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The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones

Year 2012, Volume: 16 Issue: 2, 120 - 133, 07.03.2014

Abstract

ABSTRACT: In this review, the synthesis and biological activities of 3-acyl-2,3-dihydro-1,3,4-
oxadiazole derivatives are reported. Synthesis of 1,3,4-oxadiazolines via carboxylic acid
hydrazide-hydrazones by using acetic anhydride or other cyclization agents establishes the
peculiar basis of our work.
KEYWORDS: 2,3-dihydro-1,3,4-oxadiazole, 3-acyl-1,3,4-oxadiazoline, hydrazide hydrazones,
biological activities.

References

  • Kitaev YP, Buzykin BI. The Reactions of Hydrazones. Russian Chem Rev 1972;41: 495-515.
  • Rollas S. Synthesis and Spectrometric Analysis of Some Hydrazide Hydrazones I. J Fac Pharm Ist l98l; l7: 4l-50.
  • Rollas S, Büyüktimkin S, Büyüktimkin N, Ülgen M. Yem- eni E. Evaluation of some arylhydrazones of N 2-aryli- denebenzylic acid hydrazide as antimicroial agents. Pharmazie 1988; 43: 511.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Kan- demirli F, Shvets N, Rollas S, Anatholy D. Synthesis and characterization of novel hydrazide-hydrazones and the study their structure-antituberculosis activity. Eur J Med Chem 2006; 41: 1253-61.
  • Rollas S, Küçükgüzel ŞG. Biological activities of hydra- zone derivatives. Molecules 2007; 12: 1910-39.
  • Ergenç N, Günay NS. Synthesis and antidepressant eval- uation of new 3-phenyl-5-sulfonamidoindole deriva- tives. Eur J Med Chem 1993; 33: 143-8.
  • Ling A, Plewe M, Gonzalez J, Madsen P, Sams CK, Lau J, Gregor V, Murphy D, Teston K, Kuki A, Shi S, Trues- dale L, Kiel D, May J, Lakis J, Anderes K, Iatsimirskaia E, Sidelmann UG, LB Knudsen, Brand CL, Polinsky A. Hu- man glucagon receptor antagonists based on alkylidene hydrazides. Bioorg Med Chem Lett 2002; 12: 663–6.
  • Perdicchia D, Licandro E, Maiorana S, Baldoli C, Gian- nini C. A new ‘one-pot’ synthesis of hydrazides by re- duction of hydrazones. Tetrahedron 2003; 59: 7733–42.
  • Elassar A-ZH, Dib HH, Al-Awadi NA, Elnagdi MH. Chemistry of carbofunctionally substituted hydrazones. Arkivoc 2007; (ii): 272-315.
  • Belskaya NP, Dehaen W, Bakulev VA. Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions. Arkivoc 2010; (i): 275-332.
  • Richardson DR, Milnes K. The potential of iron chela- tors of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents II: The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood 1997; 89: 3025-38.
  • Khattab SN. Synthesis and biological activity of novel amino acid-(N’-benzoyl)hydrazide and amino acid-(N’- nicotinoyl)hydrazide derivatives. Molecules 2005; 10: 1218-28.
  • Johnson DK, Murphy TB, Rose NJ. Cytotoxic chelators and chelates 1. Inhibition of DNA synthesis in cultured rodent and human cells by aroylhydrazones and by a copper (II) complex of salicylaldehyde benzoyl hydra- zone. Inorg Chim Acta 1982; 67: 159-165.
  • Richardson DR, Ponka P. Pyridoxal isonicotinoyl hy- drazone and its analogs: Potential orally effective iron- chelating agents fort the treatment of iron overload dis- ease. J Lab Clin Med 1998; 131: 307-15.
  • Mohareb RM, Fleita DH, Sakka OK. Novel synthesis of hydrazide-hydrazones derivatives and their utilization in the synthesis of coumarin, pyridine, thiazole and thi- ophene derivatives with antitumor activity. Molecules 2011; 16: 16-27.
  • Cui Z, Li Y, Ling Y, Huang J, Cui J, Wang R, Yang X. New class of potent antitumor acylhydrazone derivatives con- taining furan. Eur J Med Chem 2010; 45: 5576-84.
  • Ajani OO, Obafemi CA, Nwinyi OC, Akinpelu DA. Mi- crowave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg Med Chem 2010; 18: 214-21.
  • Narasimhan B, Kumar P, Sharma D. Biological activities of hydrazide derivatives in the new millennium. Acta Pharma Sci 2010; 52: 169-180.
  • Uppal G, Bala S, Kamboj S, Saini M. Therapeutic Review Exploring Antimicrobial potential of hydrazones as promising lead. der pharma chem 2011; 3: 250-68.
  • Küçükgüzel ŞG, Mazi A, Şahin F, Öztürk S, Stables JP. Synthesis and biological activities of diflunisal hy- drazide-hydrazones. Eur J Med Chem 2003; 38: 1005-13.
  • Özdemir A, Kaplancıklı ZA, Turan-Zitouni G, Revial G. Synthesis of some novel hydrazone derivatives and eval- uation of their antituberculosis activity. Marmara Pharm J 2010; 14:79-83.
  • Gülerman NN, Oruç EE, Kartal F, Rollas S. In vivo me- tabolism of 4-fluorobenzoic acid [(5-nitro-2-furanyl) methylene] hydrazide in rats. Eur J Drug Metab Pharma- cokinet 2000; 25: 103-8.
  • Kömürcü ŞG, Rollas S, Ülgen M, Gorrod JW, Çevikbaş A. Evaluation of some arylhydrazones of p-aminobenzoic acid hydrazide as antimicrobial agents and their in vitro hepatic microsomal metabolism. Boll Chim Farmaceuti- co-Anno 1995; 134: 281-5.
  • Imramovsky´ A, Polanc S, Vinšová J, Kočevar M, Jam- pílek J, Zuzana Rečková, Kaustová J. A new modification of anti-tubercular active molecules. Bioorg Med Chem 2007; 15: 2551–59.
  • Rollas S. Preclinical Development Handbook: ADME and Biopharmaceutical Properties Editors: Shayne Cox Gad, John Wiley & Sons, Inc. New Jersey 2008, pp. 829-851.
  • Rollas S, Kucukguzel ŞG. Hydrazone, amide, carbamate, macromolecular and other prodrugs of Doxorubicin. Open Drug Deliv J 2008; 2: 77-85.
  • Bildstein l, Dubernet C, Couvreur P. Prodrug-based in- tracellular delivery of anticancer agents. Adv Drug Deliv Rev 2011; 63: 2-23.
  • Rawat J, Jain PK, Ravichandran V, Agrawal RK. Synthe- sis and evaluation of mutual prodrugs of isoniazid, p- amino salicylic acid and ethambutol. Arkivoc 2007; (i): 105-118.
  • Kratz F. DOXO-EMCH (INNO-206): the first albumin- binding prodrug of doxorubicin to enter clinical trials. Expert Opin Investig Drugs 2007; 16: 855-66.
  • Ducry L, Stump B. Antibody-Drug Conjugates: Linking Cytotoxic Payloads to Monoclonal Antibodies. Bioconju- gate Chem 2010; 21: 5–13.
  • Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterization and biological activity of novel 4-thiazolidino 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37: 197-206.
  • Cesur N, Cesur Z, Ergenç N, Uzun M, Kiraz M, Kasimo- glu Ö, Kaya D. Synthesis and antifungal activity of some 2-aryl-3-substituted 4-thiazolidinones. Arch Pharm (Weinheim) 1994; 327: 271-72.
  • Kalsi R, Shrimali M, Bhalla TN, Barthwal JP. Synthesis and anti-inflammatory activity of indolyl azetidinones. Indian J Pharm Sci 2006; 41: 353-59.
  • Kumar D, Bux FB, Singh Arun. Synthesis and biological activity of azetidinone. Rasāyan J Chem 2010; 3: 497-502.
  • Mansour AK, Eid MM, Khalil NSAM. Synthesis and re- actions of some new heterocyclic carbohydrazides and related compounds as potantial anticancer agents. Mol- ecules 2003; 8: 744-55.
  • Dobrotă C, Paraschivescu CC, Dumitru I, Matache M, Baciu I, Rută LL. Convenient preparation of unsymmet- rical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess-Martin reagent. Tetrahedron Lett 2009; 50: 1886-88.
  • Safieh KAA, Al-Titi AMS, Zahra JA, Ayoub MT. Oxida- tive cyclization of arylidene carboxyhydrazides: Synthe- sis of substituted hydroxydiphenylmethyl-1,3,4-oxadia- zoles. JJC 2007; 2: 211-8.
  • Kovařiková P, Mokry M, Klimeš J, Vávrová K. HPLC study on stability of pyridoxal isonicotinoyl hydrazone. J Pharmaceut Biomed Anal 2006; 40: 105-112.
  • Ülgen M, Barlas-Durgun B, Rollas S, Gorrod JW. The in-vitro hepatic microsomal metabolism of benzoic acid benzylidene hydrazide. Drug Metabol Drug Interact 1997; 13: 285-94.
  • Hearn MJ, Chanyaputhipong PY. Preparation and spec- troscopic properties of 3-acyl-1,3,4-oxadiazolines. J Het- erocyclic Chem 1995; 32: 1647-49.
  • Yale HL, Losee K, Martins J, Holsing M, Perry FM, Bern- stein J. Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc 1953; 75: 1933-42.
  • Somogyi Lászlό. Structure and reactions of aldose semi- carbazone and thiosemicarbazone derivatives under acetylating conditions. Carbohydr Res 1979; 75: 325-30.
  • Hassan E, Al-Ashmawi MI, Abdel-Fattah B. Synthesis and antimicrobial testing of certain oxadiazoline and triazole derivatives. Pharmazie 1983; 38: 833-5.
  • Ergenç N, Rollas S, Topaloğlu Y, Ötük G. Synthesis and characterization of new 1,3,4-oxadiazolines. Arch Pharm 1989; 322: 837-8.
  • Rollas S, Gülerman NN, Erdeniz H. Synthesis and an- timicrobial activity of some new hydrazones of 4-fluor- obenzoic acid hydrazide and 3-acetyl-2,5-disubstituted- 1,3,4-oxadiazolines. Farmaco 2002; 57: 171-4.
  • Rahman MMA, EL Ashry ESH, Abdallah AA, Rashed N.C-(Polyacetoxy)alkyloxadiazolines and related com- pounds. Carbohydr Res 1979; 73: 103-11.
  • Maccioni E, Alcaro S, Cirilli R, Vigo S, Cardia MC, Sanna ML, Meleddu R, Yanez M, Costa G, Casu L, Matyus P, Distinto S. 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadia- zoles: A new scaffold for the selective inhibition of Mon- aamine Oxidase B. J Med Chem 2011; 54: 6394-98.
  • Somogyi L. Notes on the reactions of ketone acylhydra- zones under acylation conditions. Tetrahedron 1985; 41: 5187-90.
  • Somogyi L. Stereochemical aspects of the formation of diastereo isomeric 3-acetyl-2-(polyacetoxyalkyl)-5-phe- nyl-2,3-dihydro-1,3,4-oxadiazoles. Carbohydr Res 1988; 182: 19-29.
  • Somogyi L, Czugler M, Sohár P. Synthesis and stere- ostructure of some 5,5’-disübstituted-3-acetyl-2,2’-bi-2H- 1,3,4-oxa(thia)diazolines. Tetrahedron 1992; 48: 9355-62.
  • Somogyi L. Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S- acetals. Part III. [1,2] Transforma- tion of N, O-acetals: 3-Acyl-1,3,4-oxadiazolines. J Hetero- cyclic Chem 2007; 44: 1235-46.
  • Durgun B, Çapan G, Ergen N, Rollas S. Synthesis char- acterization and biological evaluation of new benzyli- denebenzohydrazides and 2, 5-disubstituted-2,3-dihy- dro-1,3,4-oxadiazolines. Pharmazie 1993; 48: 942-3.
  • Büyüktimkin S, Rollas S, Ülgen M, Ötük G. Some 1,3,4-oxadiazoline derivatives prepared by starting form benzylic acid hydrazide arylhdrazones and their antimi- crobial evaluation. Pharmazie 1990; 45: 865.
  • Fathy NM, Abdel-Motti F, Abdel-Megeid FME. Synthe- sis of some thienoquinoline derivatives with expected pharmacological activity. Com Fac Sci Univ Ank 1991; 37: 1-8.
  • Khalil MA, El-Sayed OA, El-Shamy HA. Synthesis and antimicrobial evaluation of novel oxa(thia)diazolylqui- nolines and oxa(thia)diazepino[7,6-b]quinolines. Arch Pharm (Weinheim), 1993; 326: 489-92.
  • Farghaly AAH. Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. J Chin Chem Soc 2004; 51: 147- 56.
  • Mogilaiah K, Kumara Swamy T, Vinay Chandra A, Srivani N. Microwave assisted synthesis of 1,3,4-oxadia- zolyl 1,8-naphthyridines under solvent-free conditions using solid support. Indian J Chem 2009; 48(B): 1462-65.
  • Dewangan D, Pandey A, Sivakumar T, Rajavel R, Dubey RD. Synthesis of some novel 2,5-disubstituted 1,3,4-oxa- diazole and its analgesic, anti-inflammatory, anti-bac- terial and anti-tubercular activity. Int J Chem Tech Res 2010; 2: 1397-412.
  • Burch HA. Nitrofuryl Heterocycles. V. 4-Acyl-5,5-di- alkyl-2-(5-nitro-2-furyl)-D2-1,3,4-oxadiazolines. J Med Chem1967; 10: 91-3.
  • Cerioni G, Maccioni E, Cardia MC, Vigo S, Mocci F. Characterization of 2,5-diaryl-1,3,4-oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very re- mote Hammett correlation. Magn Reson Chem 2009; 47: 727-33.
  • Osório TM, Monache FD, Chiaradia LD, Mascarello A, Stumpf TR, Zanetti CR, Silveira DB, Barardi CRM, Smâ- nia EFA, Viancelli A, Garcia LAT, Yunes RA, Nunes RJ, Smânia A. Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococ- cus aureus. Bioorg Med Chem Lett 2012, 22: 225–30.
  • Eid AI, Ragab FA, El-Ansary SL, El-Gazayerly SM, Mourad FE. Synthesis of new 7-substituted 4-methylcou- marin derivatives of antimicrobial activity. Arch Pharm (Weinheim)1994; 327: 211-3.
  • Armesto D, Gallego MG, Horspool WM, Ramos A. Un- expected reactivity of the anion derived from benzophe- none benzoylhydrazone in the presence of electrophiles. Tetrahedron Lett 1988; 29: 3581-4.
  • Bacu E, Couture A, Grandclaudon P. Synthesis and char- acterization of 2,2-disubstituted-5-(2-phenothiazin-10- ylethyl)-2,3-dihydro-1,3,4-oxadiazoles. Synth Commun 2003; 33: 143-151.
  • Islam R, Mohsin M. Synthesis of isatin, 5-chloroisatin and their D2-1,3,4-oxadiazoline derivatives for com- parative study on brine shrimp. Bangladesh J Pharmacol 2007; 2: 7-12.
  • Han D, Meng XB, Wang LN, Liu H, Yao Y, Wang Z, Yang ZJ, Liu ZM, Li ZJ. Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadi- azole derivatives and studies of the reaction mechanism. Tetrahedron: Asymmetry 2009; 20: 399-410.
  • Wang LN, Han D, Xu FF, Meng XB, Li ZJ. Microwave- assisted efficient synthesis of glucose-based 3-acetyl-5- alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives catalyzed by sodium acetate. Carbohydr Res 2009; 344: 2113-9.
  • Allam YA, Nawwar GAM . Facile synthesis of 3-spiroin- dolines. Heteroatom Chemistry 2002; 13: 207-10.
  • Abadi AH, Eissa AAH, Hassan GS. Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evalu- ation as antitumor and antiangiogenic agents. Chem Pharm Bull 2003; 51: 838-44.
  • Alho MMA, Moglioni AG, Brousse B, Moltrasio GY, D’Accorso NB. Synthesis and characterization of 2,2-dis- ubstituted thiadiazolines. Arkivoc 2000; (iv): 627-40.
  • Ke S, Li Z, Qian X. 1,3,4-Oxadiazoline-3(2H)-carboxam- ide derivatives as potential novel class monoamine oxi- dase (MAO) inhibitors: Synthesis, evaluation, and role of urea moiety. Bioorg Med Chem 2008; 16: 7565-72.
  • Ke S, Liu F, Wang N, Yang Q, Qian X. 1,3,4-Oxadiazoline derivatives as novel potential inhibitors targeting chitin biosynthesis: Design, synthesis and biological evalua- tion. Bioorg Med Chem Lett 2009; 19: 332-5.
  • Tsoleridis CA, Stephanidou-Stephanadou J, Gounaridis P, Zika H, Pozarentzi M. Unusual reaction of N-aroyld- ihydrocyclopenta-pyrazolidinol with ketenes: formation of 1,3,4-oxadiazoles. Tetrahedron 2003; 59: 4591-601.
  • Desai NC, Dodiya AM. Conventional and microwave techniques for synthesis and antimicrobial studies of novel 1-[2-(2-chloro(3-quinolyl))-5-(4-nitrophenyl)- (1,3,4-oxadiazolin-3-yl)]-3-(aryl)prop-2-en-1-ones. Med Chem Res 2011; DOI: 10.1007/s00044-011-9670-9.
  • Gülerman N, Rollas S, Kiraz M, Ekinci AC, Vidin A. Evaluation of antimycobacterial and anticonvulsant activities of new 1-(4-fluorobenzoyl)-4- substituted-thi- osemicarbazide and 5-(4-fluorophenyl)-4-substituted- 2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives. Far- maco 1997; 52: 691-5.
  • Shaker RM. The chemistry of mercapto- and thione- sub- stituted 1,2,4-triazoles and their utility in heterocyclic synthesis. Arkivoc 2006; (ix): 59-112.
  • Rollas S, Karakuş S, Barlas-Durgun B, Erdeniz H, Kiraz M. Synthesis and antimicrobial activity of some 1,4-dis- ubstituted thiosemicarbazide and 2,5- disubstituted 1,3,4-thiadiazole derivatives. Farmaco 1996; 51: 811-4.
  • Oruç EE, Rollas S, Kandemirli F, Shvets N, Dimoglo A. 1,3,4-Thiadiazole derivatives. Synthesis, structure eluci- dation, and structure-antituberculosis activity relation investigation. J Med Chem 2004; 47: 6760-67.
  • Feng D, Huang Y, Chen R, Yu Y, Song H. A novel of 2,5-disubstituted 1,3,4-oxadiazolines by the regioselec- tive cyclization of 1,4-disubstituted thiosemicarbazides. Synthesis 2007; 12: 1779-84. 80. sam K, Pole DL, Tadey T, Warkentin J. 2,2-Dialkoxy-D3- 1,3,4-oxadiazolines: Convenient Thermal Sources of Di- alkoxycarbenes. J Am Soc 1992; 114: 8751-2.
  • El Kaim L, Le Menestrel I, Morgentin R. Trichloroacetic acid hydrazones I: New formation of 1,3,4-oxadiazoles from aldehydes. Tetrahedron Lett 1998; 39: 6885-8.
  • Fuloria NK, Singh V, Shaharyar M, Ali M. Synthesis and antimicrobial evaluation of some new oxadiazoles de- rived from phenylpropionohydrazides. Molecules 2009; 14: 1898-903.
  • Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyr- role ring systems: A novel class of potential antibacte- rial and antitubercular agents. Eur J Med Chem 2008; 43: 1989-996.
  • Baquero E, Quinones W, Ribon W, Caldas ML, Sarmien- to L, Echeverri F. Effect of an oxadiazoline and a lignan on mycolic acid biosynthesis and ultrastructural changes of Mycobacterium tuberculosis. Hindawi Publishing Corporation Tuberculosis Research and Treatment 2011; 1-6.
  • Chawla R, Arora A, Parameswaran MK, Sharma PC, Michael S, Ravi TK. Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Pol Pharm 2010; 67: 247-53.
  • Yang JF, Cao H, Liu H, L, BQ, Ma YM. Synthesis and bioactivity of novel bis-heterocyclic compounds contain- ing pyrazole and oxadiazoline. J Chin Chem Soc 2011; 58: 369-75.
  • Hamdi N, Passarelli V, Romerosa A. Synthesis, spectros- copy and electrochemistry of new 4-(4-acetyl-5-substi- tuted-4,5-1,3,4-oxodiazol-2-yl)methoxy)-2H-chromen-2- ones as a novel class of potential antibacterial and anti- oxidant derivatives. CR Chimie 2011; 14: 548-55.
  • Ishii M, Jorge SD, de Oliveria AA, Palace-Berl F, Sonehara IY, Pasqualoto KFM, Tavares LC. Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and anti- fungal agents. Bioorg Med Chem 2011; 19: 6292-301.
  • Ali OM, , Amer HH, Abdel-Rahman AAH. Synthesis and antiviral valuation of sugar uracil-1-ylmethylhydra- zones and their oxadiazoline derivatives. Synthesis 2007; 18: 2823-8.
  • El-Emam AA, Alrashood KA, Al-Omar MA, Al-Tamimi AMS. Synthesis and antimicrobial activity of N’-heteroaryli- dene-1-adamantylcarbohydrazides and (±)-2-(1-adamantyl)- 4-acetyl-5-[5-(4-substitutedphenyl-3-isoxazoly)]-1,3,4-oxadi- azolines. Molecules 2012; 17: 3475-83.
  • Manojkumar P, Kochupappy R, Subbuchettiar G. Syn- thesis of coumarin heterocyclic derivatives with anti- oxidant activity anda in vitro cytotoxic activity against tumour cells. Acta Pharm 2009; 59: 159-70.
  • Jin L, Chen J, Song B, Chen Z, Yang S, Li Q, Hu D, Xu R. Synthesis, structure, and bioactivity of N’- substituted benzylidene-3,4,5-trimethoxybenzohy- drazide and 3-acetyl-2-substituted phenyl-5-(3,4,5- trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole deriva- tives. Bioorg Med Chem Lett 2006; 16: 5036-40.
  • Lee L, Robb LM, Lee M, Davis R, Mackay H, Chavda S, Babu B, O’Brien EL, Risinger AL, Mooberry SL, Lee M. Design, synthesis, and biological evaluations of 2,5-di- aryl-2,3-dihydro-1,3,4-oxadiazoline analogs of Combre- tastatin–A4. J Med Chem 2010; 53: 325-34.
  • Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Befani O, Turini P, Giovannini V, Mondovi B, Cirilli R, La Torre F. Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole deriva- tives against Monaamine oxidase. J Med Chem 2004; 47: 2071-4.
  • Doğan HN, Rollas S, Erdeniz H. Synthesis, structure elu- cidation and antimicrobial activity of some 3-hydroxy-2- naphthoic acid hydrazide dervatives. Farmaco 1998; 53: 462-7.
  • Şener G, Keyer-Uysal M, Doğan HN, Rollas S. 2-(3-Acety- loxy-2-naphthyl)-4-acetyl-5-phenyl-1,3,4-oxadiazoline suppresses pentylenetetrazol-induced convulsive and oxidative activity on mice. Acta Pharm Turcica 2003; 45: 61-7.
  • Hu Y, Lu X, Chen K, Yan R, Li QS, Zhu-HL. Design, syn- thesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin–A4 as nov- el antitubulin agents. Bioorg Med Chem 2012, 20: 903-9.
  • Koçyiğit-Kaymakçıoğlu B, Oruç-Emre EE, Ünsalan S, Tabanca N, Khan SI, Wedge DE, İşcan G, Demirci F, Rollas S. Synthesis and biological activity of hydrazide- hydrazones and their corresponding 3-acetyl-2,5-disub- stituted-2,3-dihydro-1,3,4-oxadiazoles. Med Chem Res 2011; DOI 10.1007/s00044-011-9882-z.
Year 2012, Volume: 16 Issue: 2, 120 - 133, 07.03.2014

Abstract

References

  • Kitaev YP, Buzykin BI. The Reactions of Hydrazones. Russian Chem Rev 1972;41: 495-515.
  • Rollas S. Synthesis and Spectrometric Analysis of Some Hydrazide Hydrazones I. J Fac Pharm Ist l98l; l7: 4l-50.
  • Rollas S, Büyüktimkin S, Büyüktimkin N, Ülgen M. Yem- eni E. Evaluation of some arylhydrazones of N 2-aryli- denebenzylic acid hydrazide as antimicroial agents. Pharmazie 1988; 43: 511.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Kan- demirli F, Shvets N, Rollas S, Anatholy D. Synthesis and characterization of novel hydrazide-hydrazones and the study their structure-antituberculosis activity. Eur J Med Chem 2006; 41: 1253-61.
  • Rollas S, Küçükgüzel ŞG. Biological activities of hydra- zone derivatives. Molecules 2007; 12: 1910-39.
  • Ergenç N, Günay NS. Synthesis and antidepressant eval- uation of new 3-phenyl-5-sulfonamidoindole deriva- tives. Eur J Med Chem 1993; 33: 143-8.
  • Ling A, Plewe M, Gonzalez J, Madsen P, Sams CK, Lau J, Gregor V, Murphy D, Teston K, Kuki A, Shi S, Trues- dale L, Kiel D, May J, Lakis J, Anderes K, Iatsimirskaia E, Sidelmann UG, LB Knudsen, Brand CL, Polinsky A. Hu- man glucagon receptor antagonists based on alkylidene hydrazides. Bioorg Med Chem Lett 2002; 12: 663–6.
  • Perdicchia D, Licandro E, Maiorana S, Baldoli C, Gian- nini C. A new ‘one-pot’ synthesis of hydrazides by re- duction of hydrazones. Tetrahedron 2003; 59: 7733–42.
  • Elassar A-ZH, Dib HH, Al-Awadi NA, Elnagdi MH. Chemistry of carbofunctionally substituted hydrazones. Arkivoc 2007; (ii): 272-315.
  • Belskaya NP, Dehaen W, Bakulev VA. Synthesis and properties of hydrazones bearing amide, thioamide and amidine functions. Arkivoc 2010; (i): 275-332.
  • Richardson DR, Milnes K. The potential of iron chela- tors of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents II: The mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone. Blood 1997; 89: 3025-38.
  • Khattab SN. Synthesis and biological activity of novel amino acid-(N’-benzoyl)hydrazide and amino acid-(N’- nicotinoyl)hydrazide derivatives. Molecules 2005; 10: 1218-28.
  • Johnson DK, Murphy TB, Rose NJ. Cytotoxic chelators and chelates 1. Inhibition of DNA synthesis in cultured rodent and human cells by aroylhydrazones and by a copper (II) complex of salicylaldehyde benzoyl hydra- zone. Inorg Chim Acta 1982; 67: 159-165.
  • Richardson DR, Ponka P. Pyridoxal isonicotinoyl hy- drazone and its analogs: Potential orally effective iron- chelating agents fort the treatment of iron overload dis- ease. J Lab Clin Med 1998; 131: 307-15.
  • Mohareb RM, Fleita DH, Sakka OK. Novel synthesis of hydrazide-hydrazones derivatives and their utilization in the synthesis of coumarin, pyridine, thiazole and thi- ophene derivatives with antitumor activity. Molecules 2011; 16: 16-27.
  • Cui Z, Li Y, Ling Y, Huang J, Cui J, Wang R, Yang X. New class of potent antitumor acylhydrazone derivatives con- taining furan. Eur J Med Chem 2010; 45: 5576-84.
  • Ajani OO, Obafemi CA, Nwinyi OC, Akinpelu DA. Mi- crowave assisted synthesis and antimicrobial activity of 2-quinoxalinone-3-hydrazone derivatives. Bioorg Med Chem 2010; 18: 214-21.
  • Narasimhan B, Kumar P, Sharma D. Biological activities of hydrazide derivatives in the new millennium. Acta Pharma Sci 2010; 52: 169-180.
  • Uppal G, Bala S, Kamboj S, Saini M. Therapeutic Review Exploring Antimicrobial potential of hydrazones as promising lead. der pharma chem 2011; 3: 250-68.
  • Küçükgüzel ŞG, Mazi A, Şahin F, Öztürk S, Stables JP. Synthesis and biological activities of diflunisal hy- drazide-hydrazones. Eur J Med Chem 2003; 38: 1005-13.
  • Özdemir A, Kaplancıklı ZA, Turan-Zitouni G, Revial G. Synthesis of some novel hydrazone derivatives and eval- uation of their antituberculosis activity. Marmara Pharm J 2010; 14:79-83.
  • Gülerman NN, Oruç EE, Kartal F, Rollas S. In vivo me- tabolism of 4-fluorobenzoic acid [(5-nitro-2-furanyl) methylene] hydrazide in rats. Eur J Drug Metab Pharma- cokinet 2000; 25: 103-8.
  • Kömürcü ŞG, Rollas S, Ülgen M, Gorrod JW, Çevikbaş A. Evaluation of some arylhydrazones of p-aminobenzoic acid hydrazide as antimicrobial agents and their in vitro hepatic microsomal metabolism. Boll Chim Farmaceuti- co-Anno 1995; 134: 281-5.
  • Imramovsky´ A, Polanc S, Vinšová J, Kočevar M, Jam- pílek J, Zuzana Rečková, Kaustová J. A new modification of anti-tubercular active molecules. Bioorg Med Chem 2007; 15: 2551–59.
  • Rollas S. Preclinical Development Handbook: ADME and Biopharmaceutical Properties Editors: Shayne Cox Gad, John Wiley & Sons, Inc. New Jersey 2008, pp. 829-851.
  • Rollas S, Kucukguzel ŞG. Hydrazone, amide, carbamate, macromolecular and other prodrugs of Doxorubicin. Open Drug Deliv J 2008; 2: 77-85.
  • Bildstein l, Dubernet C, Couvreur P. Prodrug-based in- tracellular delivery of anticancer agents. Adv Drug Deliv Rev 2011; 63: 2-23.
  • Rawat J, Jain PK, Ravichandran V, Agrawal RK. Synthe- sis and evaluation of mutual prodrugs of isoniazid, p- amino salicylic acid and ethambutol. Arkivoc 2007; (i): 105-118.
  • Kratz F. DOXO-EMCH (INNO-206): the first albumin- binding prodrug of doxorubicin to enter clinical trials. Expert Opin Investig Drugs 2007; 16: 855-66.
  • Ducry L, Stump B. Antibody-Drug Conjugates: Linking Cytotoxic Payloads to Monoclonal Antibodies. Bioconju- gate Chem 2010; 21: 5–13.
  • Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterization and biological activity of novel 4-thiazolidino 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37: 197-206.
  • Cesur N, Cesur Z, Ergenç N, Uzun M, Kiraz M, Kasimo- glu Ö, Kaya D. Synthesis and antifungal activity of some 2-aryl-3-substituted 4-thiazolidinones. Arch Pharm (Weinheim) 1994; 327: 271-72.
  • Kalsi R, Shrimali M, Bhalla TN, Barthwal JP. Synthesis and anti-inflammatory activity of indolyl azetidinones. Indian J Pharm Sci 2006; 41: 353-59.
  • Kumar D, Bux FB, Singh Arun. Synthesis and biological activity of azetidinone. Rasāyan J Chem 2010; 3: 497-502.
  • Mansour AK, Eid MM, Khalil NSAM. Synthesis and re- actions of some new heterocyclic carbohydrazides and related compounds as potantial anticancer agents. Mol- ecules 2003; 8: 744-55.
  • Dobrotă C, Paraschivescu CC, Dumitru I, Matache M, Baciu I, Rută LL. Convenient preparation of unsymmet- rical 2,5-disubstituted 1,3,4-oxadiazoles promoted by Dess-Martin reagent. Tetrahedron Lett 2009; 50: 1886-88.
  • Safieh KAA, Al-Titi AMS, Zahra JA, Ayoub MT. Oxida- tive cyclization of arylidene carboxyhydrazides: Synthe- sis of substituted hydroxydiphenylmethyl-1,3,4-oxadia- zoles. JJC 2007; 2: 211-8.
  • Kovařiková P, Mokry M, Klimeš J, Vávrová K. HPLC study on stability of pyridoxal isonicotinoyl hydrazone. J Pharmaceut Biomed Anal 2006; 40: 105-112.
  • Ülgen M, Barlas-Durgun B, Rollas S, Gorrod JW. The in-vitro hepatic microsomal metabolism of benzoic acid benzylidene hydrazide. Drug Metabol Drug Interact 1997; 13: 285-94.
  • Hearn MJ, Chanyaputhipong PY. Preparation and spec- troscopic properties of 3-acyl-1,3,4-oxadiazolines. J Het- erocyclic Chem 1995; 32: 1647-49.
  • Yale HL, Losee K, Martins J, Holsing M, Perry FM, Bern- stein J. Chemotherapy of experimental tuberculosis. VIII. The synthesis of acid hydrazides, their derivatives and related compounds. J Am Chem Soc 1953; 75: 1933-42.
  • Somogyi Lászlό. Structure and reactions of aldose semi- carbazone and thiosemicarbazone derivatives under acetylating conditions. Carbohydr Res 1979; 75: 325-30.
  • Hassan E, Al-Ashmawi MI, Abdel-Fattah B. Synthesis and antimicrobial testing of certain oxadiazoline and triazole derivatives. Pharmazie 1983; 38: 833-5.
  • Ergenç N, Rollas S, Topaloğlu Y, Ötük G. Synthesis and characterization of new 1,3,4-oxadiazolines. Arch Pharm 1989; 322: 837-8.
  • Rollas S, Gülerman NN, Erdeniz H. Synthesis and an- timicrobial activity of some new hydrazones of 4-fluor- obenzoic acid hydrazide and 3-acetyl-2,5-disubstituted- 1,3,4-oxadiazolines. Farmaco 2002; 57: 171-4.
  • Rahman MMA, EL Ashry ESH, Abdallah AA, Rashed N.C-(Polyacetoxy)alkyloxadiazolines and related com- pounds. Carbohydr Res 1979; 73: 103-11.
  • Maccioni E, Alcaro S, Cirilli R, Vigo S, Cardia MC, Sanna ML, Meleddu R, Yanez M, Costa G, Casu L, Matyus P, Distinto S. 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadia- zoles: A new scaffold for the selective inhibition of Mon- aamine Oxidase B. J Med Chem 2011; 54: 6394-98.
  • Somogyi L. Notes on the reactions of ketone acylhydra- zones under acylation conditions. Tetrahedron 1985; 41: 5187-90.
  • Somogyi L. Stereochemical aspects of the formation of diastereo isomeric 3-acetyl-2-(polyacetoxyalkyl)-5-phe- nyl-2,3-dihydro-1,3,4-oxadiazoles. Carbohydr Res 1988; 182: 19-29.
  • Somogyi L, Czugler M, Sohár P. Synthesis and stere- ostructure of some 5,5’-disübstituted-3-acetyl-2,2’-bi-2H- 1,3,4-oxa(thia)diazolines. Tetrahedron 1992; 48: 9355-62.
  • Somogyi L. Synthesis, oxidation and dehydrogenation of cyclic N,O- and N,S- acetals. Part III. [1,2] Transforma- tion of N, O-acetals: 3-Acyl-1,3,4-oxadiazolines. J Hetero- cyclic Chem 2007; 44: 1235-46.
  • Durgun B, Çapan G, Ergen N, Rollas S. Synthesis char- acterization and biological evaluation of new benzyli- denebenzohydrazides and 2, 5-disubstituted-2,3-dihy- dro-1,3,4-oxadiazolines. Pharmazie 1993; 48: 942-3.
  • Büyüktimkin S, Rollas S, Ülgen M, Ötük G. Some 1,3,4-oxadiazoline derivatives prepared by starting form benzylic acid hydrazide arylhdrazones and their antimi- crobial evaluation. Pharmazie 1990; 45: 865.
  • Fathy NM, Abdel-Motti F, Abdel-Megeid FME. Synthe- sis of some thienoquinoline derivatives with expected pharmacological activity. Com Fac Sci Univ Ank 1991; 37: 1-8.
  • Khalil MA, El-Sayed OA, El-Shamy HA. Synthesis and antimicrobial evaluation of novel oxa(thia)diazolylqui- nolines and oxa(thia)diazepino[7,6-b]quinolines. Arch Pharm (Weinheim), 1993; 326: 489-92.
  • Farghaly AAH. Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. J Chin Chem Soc 2004; 51: 147- 56.
  • Mogilaiah K, Kumara Swamy T, Vinay Chandra A, Srivani N. Microwave assisted synthesis of 1,3,4-oxadia- zolyl 1,8-naphthyridines under solvent-free conditions using solid support. Indian J Chem 2009; 48(B): 1462-65.
  • Dewangan D, Pandey A, Sivakumar T, Rajavel R, Dubey RD. Synthesis of some novel 2,5-disubstituted 1,3,4-oxa- diazole and its analgesic, anti-inflammatory, anti-bac- terial and anti-tubercular activity. Int J Chem Tech Res 2010; 2: 1397-412.
  • Burch HA. Nitrofuryl Heterocycles. V. 4-Acyl-5,5-di- alkyl-2-(5-nitro-2-furyl)-D2-1,3,4-oxadiazolines. J Med Chem1967; 10: 91-3.
  • Cerioni G, Maccioni E, Cardia MC, Vigo S, Mocci F. Characterization of 2,5-diaryl-1,3,4-oxadiazolines by multinuclear magnetic resonance and density functional theory calculations. Investigation on a case of very re- mote Hammett correlation. Magn Reson Chem 2009; 47: 727-33.
  • Osório TM, Monache FD, Chiaradia LD, Mascarello A, Stumpf TR, Zanetti CR, Silveira DB, Barardi CRM, Smâ- nia EFA, Viancelli A, Garcia LAT, Yunes RA, Nunes RJ, Smânia A. Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococ- cus aureus. Bioorg Med Chem Lett 2012, 22: 225–30.
  • Eid AI, Ragab FA, El-Ansary SL, El-Gazayerly SM, Mourad FE. Synthesis of new 7-substituted 4-methylcou- marin derivatives of antimicrobial activity. Arch Pharm (Weinheim)1994; 327: 211-3.
  • Armesto D, Gallego MG, Horspool WM, Ramos A. Un- expected reactivity of the anion derived from benzophe- none benzoylhydrazone in the presence of electrophiles. Tetrahedron Lett 1988; 29: 3581-4.
  • Bacu E, Couture A, Grandclaudon P. Synthesis and char- acterization of 2,2-disubstituted-5-(2-phenothiazin-10- ylethyl)-2,3-dihydro-1,3,4-oxadiazoles. Synth Commun 2003; 33: 143-151.
  • Islam R, Mohsin M. Synthesis of isatin, 5-chloroisatin and their D2-1,3,4-oxadiazoline derivatives for com- parative study on brine shrimp. Bangladesh J Pharmacol 2007; 2: 7-12.
  • Han D, Meng XB, Wang LN, Liu H, Yao Y, Wang Z, Yang ZJ, Liu ZM, Li ZJ. Efficient synthesis of a series of novel fructose-based 3-acetyl-5-alkyl-2,3-dihydro-1,3,4-oxadi- azole derivatives and studies of the reaction mechanism. Tetrahedron: Asymmetry 2009; 20: 399-410.
  • Wang LN, Han D, Xu FF, Meng XB, Li ZJ. Microwave- assisted efficient synthesis of glucose-based 3-acetyl-5- alkyl-2,3-dihydro-1,3,4-oxadiazole derivatives catalyzed by sodium acetate. Carbohydr Res 2009; 344: 2113-9.
  • Allam YA, Nawwar GAM . Facile synthesis of 3-spiroin- dolines. Heteroatom Chemistry 2002; 13: 207-10.
  • Abadi AH, Eissa AAH, Hassan GS. Synthesis of novel 1,3,4-trisubstituted pyrazole derivatives and their evalu- ation as antitumor and antiangiogenic agents. Chem Pharm Bull 2003; 51: 838-44.
  • Alho MMA, Moglioni AG, Brousse B, Moltrasio GY, D’Accorso NB. Synthesis and characterization of 2,2-dis- ubstituted thiadiazolines. Arkivoc 2000; (iv): 627-40.
  • Ke S, Li Z, Qian X. 1,3,4-Oxadiazoline-3(2H)-carboxam- ide derivatives as potential novel class monoamine oxi- dase (MAO) inhibitors: Synthesis, evaluation, and role of urea moiety. Bioorg Med Chem 2008; 16: 7565-72.
  • Ke S, Liu F, Wang N, Yang Q, Qian X. 1,3,4-Oxadiazoline derivatives as novel potential inhibitors targeting chitin biosynthesis: Design, synthesis and biological evalua- tion. Bioorg Med Chem Lett 2009; 19: 332-5.
  • Tsoleridis CA, Stephanidou-Stephanadou J, Gounaridis P, Zika H, Pozarentzi M. Unusual reaction of N-aroyld- ihydrocyclopenta-pyrazolidinol with ketenes: formation of 1,3,4-oxadiazoles. Tetrahedron 2003; 59: 4591-601.
  • Desai NC, Dodiya AM. Conventional and microwave techniques for synthesis and antimicrobial studies of novel 1-[2-(2-chloro(3-quinolyl))-5-(4-nitrophenyl)- (1,3,4-oxadiazolin-3-yl)]-3-(aryl)prop-2-en-1-ones. Med Chem Res 2011; DOI: 10.1007/s00044-011-9670-9.
  • Gülerman N, Rollas S, Kiraz M, Ekinci AC, Vidin A. Evaluation of antimycobacterial and anticonvulsant activities of new 1-(4-fluorobenzoyl)-4- substituted-thi- osemicarbazide and 5-(4-fluorophenyl)-4-substituted- 2,4-dihydro-3H-1,2,4-triazole-3-thione derivatives. Far- maco 1997; 52: 691-5.
  • Shaker RM. The chemistry of mercapto- and thione- sub- stituted 1,2,4-triazoles and their utility in heterocyclic synthesis. Arkivoc 2006; (ix): 59-112.
  • Rollas S, Karakuş S, Barlas-Durgun B, Erdeniz H, Kiraz M. Synthesis and antimicrobial activity of some 1,4-dis- ubstituted thiosemicarbazide and 2,5- disubstituted 1,3,4-thiadiazole derivatives. Farmaco 1996; 51: 811-4.
  • Oruç EE, Rollas S, Kandemirli F, Shvets N, Dimoglo A. 1,3,4-Thiadiazole derivatives. Synthesis, structure eluci- dation, and structure-antituberculosis activity relation investigation. J Med Chem 2004; 47: 6760-67.
  • Feng D, Huang Y, Chen R, Yu Y, Song H. A novel of 2,5-disubstituted 1,3,4-oxadiazolines by the regioselec- tive cyclization of 1,4-disubstituted thiosemicarbazides. Synthesis 2007; 12: 1779-84. 80. sam K, Pole DL, Tadey T, Warkentin J. 2,2-Dialkoxy-D3- 1,3,4-oxadiazolines: Convenient Thermal Sources of Di- alkoxycarbenes. J Am Soc 1992; 114: 8751-2.
  • El Kaim L, Le Menestrel I, Morgentin R. Trichloroacetic acid hydrazones I: New formation of 1,3,4-oxadiazoles from aldehydes. Tetrahedron Lett 1998; 39: 6885-8.
  • Fuloria NK, Singh V, Shaharyar M, Ali M. Synthesis and antimicrobial evaluation of some new oxadiazoles de- rived from phenylpropionohydrazides. Molecules 2009; 14: 1898-903.
  • Joshi SD, Vagdevi HM, Vaidya VP, Gadaginamath GS. Synthesis of new 4-pyrrol-1-yl benzoic acid hydrazide analogs and some derived oxadiazole, triazole and pyr- role ring systems: A novel class of potential antibacte- rial and antitubercular agents. Eur J Med Chem 2008; 43: 1989-996.
  • Baquero E, Quinones W, Ribon W, Caldas ML, Sarmien- to L, Echeverri F. Effect of an oxadiazoline and a lignan on mycolic acid biosynthesis and ultrastructural changes of Mycobacterium tuberculosis. Hindawi Publishing Corporation Tuberculosis Research and Treatment 2011; 1-6.
  • Chawla R, Arora A, Parameswaran MK, Sharma PC, Michael S, Ravi TK. Synthesis of novel 1,3,4-oxadiazole derivatives as potential antimicrobial agents. Acta Pol Pharm 2010; 67: 247-53.
  • Yang JF, Cao H, Liu H, L, BQ, Ma YM. Synthesis and bioactivity of novel bis-heterocyclic compounds contain- ing pyrazole and oxadiazoline. J Chin Chem Soc 2011; 58: 369-75.
  • Hamdi N, Passarelli V, Romerosa A. Synthesis, spectros- copy and electrochemistry of new 4-(4-acetyl-5-substi- tuted-4,5-1,3,4-oxodiazol-2-yl)methoxy)-2H-chromen-2- ones as a novel class of potential antibacterial and anti- oxidant derivatives. CR Chimie 2011; 14: 548-55.
  • Ishii M, Jorge SD, de Oliveria AA, Palace-Berl F, Sonehara IY, Pasqualoto KFM, Tavares LC. Synthesis, molecular modeling and preliminary biological evaluation of a set of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole as potential antibacterial, anti-Trypanosoma cruzi and anti- fungal agents. Bioorg Med Chem 2011; 19: 6292-301.
  • Ali OM, , Amer HH, Abdel-Rahman AAH. Synthesis and antiviral valuation of sugar uracil-1-ylmethylhydra- zones and their oxadiazoline derivatives. Synthesis 2007; 18: 2823-8.
  • El-Emam AA, Alrashood KA, Al-Omar MA, Al-Tamimi AMS. Synthesis and antimicrobial activity of N’-heteroaryli- dene-1-adamantylcarbohydrazides and (±)-2-(1-adamantyl)- 4-acetyl-5-[5-(4-substitutedphenyl-3-isoxazoly)]-1,3,4-oxadi- azolines. Molecules 2012; 17: 3475-83.
  • Manojkumar P, Kochupappy R, Subbuchettiar G. Syn- thesis of coumarin heterocyclic derivatives with anti- oxidant activity anda in vitro cytotoxic activity against tumour cells. Acta Pharm 2009; 59: 159-70.
  • Jin L, Chen J, Song B, Chen Z, Yang S, Li Q, Hu D, Xu R. Synthesis, structure, and bioactivity of N’- substituted benzylidene-3,4,5-trimethoxybenzohy- drazide and 3-acetyl-2-substituted phenyl-5-(3,4,5- trimethoxyphenyl)-2,3-dihydro-1,3,4-oxadiazole deriva- tives. Bioorg Med Chem Lett 2006; 16: 5036-40.
  • Lee L, Robb LM, Lee M, Davis R, Mackay H, Chavda S, Babu B, O’Brien EL, Risinger AL, Mooberry SL, Lee M. Design, synthesis, and biological evaluations of 2,5-di- aryl-2,3-dihydro-1,3,4-oxadiazoline analogs of Combre- tastatin–A4. J Med Chem 2010; 53: 325-34.
  • Chimenti F, Bolasco A, Manna F, Secci D, Chimenti P, Befani O, Turini P, Giovannini V, Mondovi B, Cirilli R, La Torre F. Synthesis and selective inhibitory activity of 1-acetyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole deriva- tives against Monaamine oxidase. J Med Chem 2004; 47: 2071-4.
  • Doğan HN, Rollas S, Erdeniz H. Synthesis, structure elu- cidation and antimicrobial activity of some 3-hydroxy-2- naphthoic acid hydrazide dervatives. Farmaco 1998; 53: 462-7.
  • Şener G, Keyer-Uysal M, Doğan HN, Rollas S. 2-(3-Acety- loxy-2-naphthyl)-4-acetyl-5-phenyl-1,3,4-oxadiazoline suppresses pentylenetetrazol-induced convulsive and oxidative activity on mice. Acta Pharm Turcica 2003; 45: 61-7.
  • Hu Y, Lu X, Chen K, Yan R, Li QS, Zhu-HL. Design, syn- thesis, biological evaluation and molecular modeling of 1,3,4-oxadiazoline analogs of combretastatin–A4 as nov- el antitubulin agents. Bioorg Med Chem 2012, 20: 903-9.
  • Koçyiğit-Kaymakçıoğlu B, Oruç-Emre EE, Ünsalan S, Tabanca N, Khan SI, Wedge DE, İşcan G, Demirci F, Rollas S. Synthesis and biological activity of hydrazide- hydrazones and their corresponding 3-acetyl-2,5-disub- stituted-2,3-dihydro-1,3,4-oxadiazoles. Med Chem Res 2011; DOI 10.1007/s00044-011-9882-z.
There are 97 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Sevim Rollas This is me

Sevgi Karakuş This is me

Publication Date March 7, 2014
Published in Issue Year 2012 Volume: 16 Issue: 2

Cite

APA Rollas, S., & Karakuş, S. (2014). The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones. Marmara Pharmaceutical Journal, 16(2), 120-133. https://doi.org/10.12991/mpj.44775
AMA Rollas S, Karakuş S. The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones. J Res Pharm. March 2014;16(2):120-133. doi:10.12991/mpj.44775
Chicago Rollas, Sevim, and Sevgi Karakuş. “The Synthesis and Biological Activities of 3-Acyl- 2,3-Dihydro-1,3,4-Oxadiazole / 3-Acyl-1,3,4-Oxadiazoline Derivatives Obtained from Hydrazide-Hydrazones”. Marmara Pharmaceutical Journal 16, no. 2 (March 2014): 120-33. https://doi.org/10.12991/mpj.44775.
EndNote Rollas S, Karakuş S (March 1, 2014) The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones. Marmara Pharmaceutical Journal 16 2 120–133.
IEEE S. Rollas and S. Karakuş, “The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones”, J Res Pharm, vol. 16, no. 2, pp. 120–133, 2014, doi: 10.12991/mpj.44775.
ISNAD Rollas, Sevim - Karakuş, Sevgi. “The Synthesis and Biological Activities of 3-Acyl- 2,3-Dihydro-1,3,4-Oxadiazole / 3-Acyl-1,3,4-Oxadiazoline Derivatives Obtained from Hydrazide-Hydrazones”. Marmara Pharmaceutical Journal 16/2 (March 2014), 120-133. https://doi.org/10.12991/mpj.44775.
JAMA Rollas S, Karakuş S. The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones. J Res Pharm. 2014;16:120–133.
MLA Rollas, Sevim and Sevgi Karakuş. “The Synthesis and Biological Activities of 3-Acyl- 2,3-Dihydro-1,3,4-Oxadiazole / 3-Acyl-1,3,4-Oxadiazoline Derivatives Obtained from Hydrazide-Hydrazones”. Marmara Pharmaceutical Journal, vol. 16, no. 2, 2014, pp. 120-33, doi:10.12991/mpj.44775.
Vancouver Rollas S, Karakuş S. The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole / 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones. J Res Pharm. 2014;16(2):120-33.

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