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The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety

Year 2012, Volume: 16 Issue: 3, 222 - 228, 07.03.2014

Abstract

ABSTRACT: Novel derivatives of substituted hydrazone (2a-e), 2-pyrazoline-5-one (3a-e, 4ae)
and 2-isoxazoline-5-one (5a-e) derivatives possessing 1,3,4-thiadiazole moiety were synthesized
and evaluated for their antitubercular activity. The highest inhibitions were observed
with the synthesized compounds are 87% for 3-methyl-4-[4-(5-cyclohexylamino-
1,3,4-thiadiazole-2-yl)phenylhydrazono]-2-isoxazoline-5-one (5b) and 86% for ethyl
2-[4-(5-cyclohexylamino-1,3,4-thiadiazole-2-yl)phenylhydrazono]-3-oxobutirate (2b). Compounds
2b and 5b could be a good initial point to develop new lead compound.
KEY WORDS: 1,3,4-thiadiazole, 2-pyrazolin-5-one, 2-isoxazoline-5-one, hydrazone and
antitubercular activity

References

  • Maddry JA, Ananthan S, Goldman RC, Hobrath JV, Kwong CD, Maddox C, Rasmussen L, Reynolds RC, Se- crist III JA, Sosa MI, White EL, Zhang W. Antitubercu- losis activity of the molecular libraries screening center network library. Tuberculosis 2009; 89: 354-63.
  • Janin YL. Antituberculosis drugs: Ten years of research. Bioorg Med Chem 2007; 15: 2479-513.
  • Chande MS, Verma RS, Barve PA, Khanwelkar RR, Vaid- ya RB, Ajaikumar KB. Facile synthesis of active antitu- bercular, cytotoxic and antibacterial agents: a Michael addition approach. Eur J Med Chem 2005; 40: 1143-8.
  • Quesnelle CA, Gill P, Roy S, Dodier M, Marinier A, Mar- tel A, Snyder LB, S. D’Andrea SV, Bronson JJ, Frosco M, Beaulieu D, Warr GA, Denbleyker KL, Stickle TM, Yang H, Chaniewski SE, Ferraro CA, Taylor D, Russell JW, Santone KS, Clarke J, Drain RL, Knipe JO, Mosure K, Bar- rett JF. Biaryl isoxazolinone antibacterial agents. Bioorg Med Chem Lett 2005; 15: 2728-33.
  • Manojkumar P, Ravi TK, Gopalakrishnan S Antioxidant and antibacterial studies of arylazopyrazoles and aryl- hydrazonopyrazolones containing coumarin moiety. Eur J Med Chem 2009; 44: 4690-4.
  • Küçükgüzel ŞG, Rollas S, Erdeniz H, Kiraz M, Ekinci AC, Vidin A. Synthesis, characterization and pharmacologi- cal properties of some 4-arylhydrazono-2-pyrazoline- 5-one derivatives obtained from heterocyclic amines. Eur J Med Chem 2000; 35: 761-71.
  • Karakuş S. 2-(4-Aminofenil)-5-sübstitüeamino-1,3,4-ti- yadiazollerden türeyen bazı bileşiklerin sentezi ve spek- tral verileri. Ph.D. Thesis, Marmara University Institute of Health Sciences 2001.
  • Küçükgüzel ŞG, Rollas S. Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyra- zoline-5-ones as potential antimycobacterial agents. Far- maco 2002; 57 (7) : 583-7.
  • Oruç EE, Rollas S, Kandemirli F, Shvets N, Dimoglo
  • AS. 1,3,4-thiadiazole derivatives, synthesis, struc- ture elucidation and structure-antituberculosis activ- ity relationship investigation. J Med Chem 2004; 47: 6760-7.
  • Foroumadi A, Kargar Z, Sakhtemen A, Sharifzadeh Z, Feyzmohammadi R, Kazemi M, Shafiee A. Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)- 1,3,4-thiadiazol-2-ylthio]propionates. Bioorg Med Chem Lett 2006; 16:1164-7.
  • Kömürcü ŞG, Rollas S, Yılmaz N, Çevikbaş A. Synthe- sis of 3-methyl-4-[(2,4-dihydro-4-substituted-3H-1,2,4- triazole-3-thione-5-yl)phenylhydrazono]-5-isoxa-zolone and evaluation of their antimicrobial activities. Drug Metab Drug Inter 1995; 12(2): 161-8.
  • Deng BL, Hartman TL, Buckheit RW, Pannecouque C, Clercq E De, Cushman M. Replacement of the metaboli- cally labile methyl esters in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors with isoxazole, oxazolone, or cyano substituents. J Med Chem 2006; 49: 5316-23.
  • Fan X, Zhang X, Zhou L, Keith KA, Kern ER, Torrence PF. A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity. Bioorg Med Chem Lett 2006; 16: 3224-8.
  • Mavrova AT, Wesselinova D, Tsenov YA, Denkova P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on inmunocompetent cells. Eur J Med Chem 2009; 44: 63-9.
  • Wakabayashi K, Imai K, Miyachi H, Hashimoto Y, Tanatani A. 4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor. Bioorg Med Chem 2008; 16: 6799-812.
  • Laughlin SK, Clark MP, Djung JF, Golebiowski A, Brugel TA, Sabat M, Bookland RG, Laufersweiler MJ, VanRens JC, Townes JA, De B, Hsieh LC, Xu SC, Walter RL, Me- kel MJ, Janusz MJ. The development of new isoxazolone based inhibitors of tumor necrosis factor-alpha (TNF-α) production. Bioorg Med Chem Lett 2005; 15: 2399-403.
  • Ishioka T, Kubo A, Koiso Y, Nagasawa K, Itai A, Hashi- moto Y. Novel non-steroidal /non-anilide type andro- gen antagonist with an isoxazolone moiety. Bioorg Med Chem 2002; 10: 1555-66.
  • Conchon E, Aboab B, Goldsteyn RM, Cruzalegui F, Ed- monds T, Léonce S, Pfeiffer B, Prudhomme M. Synthesis, in vitro antiproliferative activities and Chk1 inhibitory properties of indolylpyrazolones and indolylpyridazin- edione. Eur J Med Chem 2006; 41: 1470-7.
  • El-Hawash SAM, Badawey SAM, El-Ashmawey IM. Nonsteroidal antiinflamatory agents part-2 antiinflama- tory, analgesic and antipyretic activity of some sustituted 3-pyrazolin-5-ones and 1,2,4,5,6,7-3H-hexahydroindol- 3-ones. Eur J Med Chem 2006; 41: 155-65.
  • Girges MM, Hana MA, Rasal D, Berghot M. Potentially active hypoglycemic agents from N1-nicotinoyl-2-pyra- zolin-5-one derivatives and their N1-(oxynicotinoyl)ana- logues. Arzneim-Forsch./Drug Res 1992; 42: 1350-3.
  • Golebiowski A, Townes JA, Laufersweiler MJ, Brugel TA, Clark MP, Clark CM, Djung JF, Laughlin SK, Sabat MP, Bookland RG, VanRens JC, De B, Hsieh LC, Janusz MJ, Walter RL, Webster ME, Mekel MJ.: The develop- ment of monocyclic pyrazolone based cytokine synthesis inhibitors. Bioorg Med Chem Lett 2005; 15: 2285-9.
  • Chen T, Benmohammed R, Kim J, Smith K, Amante D, MorimotoRI, KirschDR, Ferrante RJ, Silverman RB. ADME-guided design and synthesis of aryloxanyl pyra- zolone derivatives to block mutant superoxide dismutase 1 (SOD1) cytotoxicity and protein aggregation:potential application fort he treatment of amyotrophic lateral scle- rosis. J Med Chem 2012; 55: 515-27.
  • Anderegg TR, Sader HS, Fritsche TR, Ross JE, Jones RN. Trends in linezolid susceptibility patterns: report from the 2002-2003 worldwide Zyvox Annual Appraisal of Potency and Spectrum (ZAAPS) Program. Int J Antimicr Agents 2005; 26: 13-21.
  • Von der Lippe B, Sandven P, Brubakk O. Efficacy and safety of linezolid in multidrug resistand tuberculosis. J Infect 2006; 52: 92-6.
  • Prammananan T, Chaiprasert A, Leechawengwongs M. In vitro activity of linezolid against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant (XDR)-TB isolates. Int J Antimicrob Agents 2009; 33: 190-1.
  • Solak N, Rollas S. Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadia- zoles and their Shiff bases. ARKIVOC 2006; 12: 173-81.
  • Karakuş S, Çoruh U, Barlas-Durgun B, Vázquez-López EM, Özbaş-Turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted-1,3,4-thiadiazole derivatives. Marmara Pharm J 2010; 14(2): 84-90.
  • Rollas S, Kokyan Ş, Koçyiğit-Kaymakcıoğlu B, Özbaş- Turan S, Akbuga J. Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. Marmara Pharm J 2011; 15: 94-9.
  • Rollas S. Cleavage of azo compounds with hydrazine hydrate and some new 1,3,4-thiadiazole derivatives. J Pharm Univ Mar 1985; 1: 59-68.
  • Rollas S. Reduction of aromatic and heteroaromatic azo compounds with hydrazine hydrate. Marmara Pharm J 2010; 14: 41-6.
  • Özger Y, Rollas S. Reductive cleavage of azo compounds with hydrazine and some 1,3,4-thiadiazole derivatives III. J Pharm Univ Mar 1988; 5: 133-41.
  • Ergenç N, Rollas S The coupling products of aliphatic ac- tive C-H compounds with diazonium salts I. J Fac Pharm Istanbul 1975; 11: 8-23.
  • Collins L, Franzblau SG. Microplate alamar blue assay vesus BACTEC 460 system for high-throughput screen- ing of compoundsagainst Myccbacterium tuberculosis and Myccbacterium avium. Antimicrob Agents Chem- other 1997; 41: 1004-9.

The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety

Year 2012, Volume: 16 Issue: 3, 222 - 228, 07.03.2014

Abstract

References

  • Maddry JA, Ananthan S, Goldman RC, Hobrath JV, Kwong CD, Maddox C, Rasmussen L, Reynolds RC, Se- crist III JA, Sosa MI, White EL, Zhang W. Antitubercu- losis activity of the molecular libraries screening center network library. Tuberculosis 2009; 89: 354-63.
  • Janin YL. Antituberculosis drugs: Ten years of research. Bioorg Med Chem 2007; 15: 2479-513.
  • Chande MS, Verma RS, Barve PA, Khanwelkar RR, Vaid- ya RB, Ajaikumar KB. Facile synthesis of active antitu- bercular, cytotoxic and antibacterial agents: a Michael addition approach. Eur J Med Chem 2005; 40: 1143-8.
  • Quesnelle CA, Gill P, Roy S, Dodier M, Marinier A, Mar- tel A, Snyder LB, S. D’Andrea SV, Bronson JJ, Frosco M, Beaulieu D, Warr GA, Denbleyker KL, Stickle TM, Yang H, Chaniewski SE, Ferraro CA, Taylor D, Russell JW, Santone KS, Clarke J, Drain RL, Knipe JO, Mosure K, Bar- rett JF. Biaryl isoxazolinone antibacterial agents. Bioorg Med Chem Lett 2005; 15: 2728-33.
  • Manojkumar P, Ravi TK, Gopalakrishnan S Antioxidant and antibacterial studies of arylazopyrazoles and aryl- hydrazonopyrazolones containing coumarin moiety. Eur J Med Chem 2009; 44: 4690-4.
  • Küçükgüzel ŞG, Rollas S, Erdeniz H, Kiraz M, Ekinci AC, Vidin A. Synthesis, characterization and pharmacologi- cal properties of some 4-arylhydrazono-2-pyrazoline- 5-one derivatives obtained from heterocyclic amines. Eur J Med Chem 2000; 35: 761-71.
  • Karakuş S. 2-(4-Aminofenil)-5-sübstitüeamino-1,3,4-ti- yadiazollerden türeyen bazı bileşiklerin sentezi ve spek- tral verileri. Ph.D. Thesis, Marmara University Institute of Health Sciences 2001.
  • Küçükgüzel ŞG, Rollas S. Synthesis, characterization of novel coupling products and 4-arylhydrazono-2-pyra- zoline-5-ones as potential antimycobacterial agents. Far- maco 2002; 57 (7) : 583-7.
  • Oruç EE, Rollas S, Kandemirli F, Shvets N, Dimoglo
  • AS. 1,3,4-thiadiazole derivatives, synthesis, struc- ture elucidation and structure-antituberculosis activ- ity relationship investigation. J Med Chem 2004; 47: 6760-7.
  • Foroumadi A, Kargar Z, Sakhtemen A, Sharifzadeh Z, Feyzmohammadi R, Kazemi M, Shafiee A. Synthesis and antimycobacterial activity of some alkyl [5-(nitroaryl)- 1,3,4-thiadiazol-2-ylthio]propionates. Bioorg Med Chem Lett 2006; 16:1164-7.
  • Kömürcü ŞG, Rollas S, Yılmaz N, Çevikbaş A. Synthe- sis of 3-methyl-4-[(2,4-dihydro-4-substituted-3H-1,2,4- triazole-3-thione-5-yl)phenylhydrazono]-5-isoxa-zolone and evaluation of their antimicrobial activities. Drug Metab Drug Inter 1995; 12(2): 161-8.
  • Deng BL, Hartman TL, Buckheit RW, Pannecouque C, Clercq E De, Cushman M. Replacement of the metaboli- cally labile methyl esters in the alkenyldiarylmethane series of non-nucleoside reverse transcriptase inhibitors with isoxazole, oxazolone, or cyano substituents. J Med Chem 2006; 49: 5316-23.
  • Fan X, Zhang X, Zhou L, Keith KA, Kern ER, Torrence PF. A pyrimidine-pyrazolone nucleoside chimera with potent in vitro anti-orthopoxvirus activity. Bioorg Med Chem Lett 2006; 16: 3224-8.
  • Mavrova AT, Wesselinova D, Tsenov YA, Denkova P. Synthesis, cytotoxicity and effects of some 1,2,4-triazole and 1,3,4-thiadiazole derivatives on inmunocompetent cells. Eur J Med Chem 2009; 44: 63-9.
  • Wakabayashi K, Imai K, Miyachi H, Hashimoto Y, Tanatani A. 4-(Anilino)pyrrole-2-carboxamides: Novel non-steroidal/non-anilide type androgen antagonists effective upon human prostate tumor LNCaP cells with mutated nuclear androgen receptor. Bioorg Med Chem 2008; 16: 6799-812.
  • Laughlin SK, Clark MP, Djung JF, Golebiowski A, Brugel TA, Sabat M, Bookland RG, Laufersweiler MJ, VanRens JC, Townes JA, De B, Hsieh LC, Xu SC, Walter RL, Me- kel MJ, Janusz MJ. The development of new isoxazolone based inhibitors of tumor necrosis factor-alpha (TNF-α) production. Bioorg Med Chem Lett 2005; 15: 2399-403.
  • Ishioka T, Kubo A, Koiso Y, Nagasawa K, Itai A, Hashi- moto Y. Novel non-steroidal /non-anilide type andro- gen antagonist with an isoxazolone moiety. Bioorg Med Chem 2002; 10: 1555-66.
  • Conchon E, Aboab B, Goldsteyn RM, Cruzalegui F, Ed- monds T, Léonce S, Pfeiffer B, Prudhomme M. Synthesis, in vitro antiproliferative activities and Chk1 inhibitory properties of indolylpyrazolones and indolylpyridazin- edione. Eur J Med Chem 2006; 41: 1470-7.
  • El-Hawash SAM, Badawey SAM, El-Ashmawey IM. Nonsteroidal antiinflamatory agents part-2 antiinflama- tory, analgesic and antipyretic activity of some sustituted 3-pyrazolin-5-ones and 1,2,4,5,6,7-3H-hexahydroindol- 3-ones. Eur J Med Chem 2006; 41: 155-65.
  • Girges MM, Hana MA, Rasal D, Berghot M. Potentially active hypoglycemic agents from N1-nicotinoyl-2-pyra- zolin-5-one derivatives and their N1-(oxynicotinoyl)ana- logues. Arzneim-Forsch./Drug Res 1992; 42: 1350-3.
  • Golebiowski A, Townes JA, Laufersweiler MJ, Brugel TA, Clark MP, Clark CM, Djung JF, Laughlin SK, Sabat MP, Bookland RG, VanRens JC, De B, Hsieh LC, Janusz MJ, Walter RL, Webster ME, Mekel MJ.: The develop- ment of monocyclic pyrazolone based cytokine synthesis inhibitors. Bioorg Med Chem Lett 2005; 15: 2285-9.
  • Chen T, Benmohammed R, Kim J, Smith K, Amante D, MorimotoRI, KirschDR, Ferrante RJ, Silverman RB. ADME-guided design and synthesis of aryloxanyl pyra- zolone derivatives to block mutant superoxide dismutase 1 (SOD1) cytotoxicity and protein aggregation:potential application fort he treatment of amyotrophic lateral scle- rosis. J Med Chem 2012; 55: 515-27.
  • Anderegg TR, Sader HS, Fritsche TR, Ross JE, Jones RN. Trends in linezolid susceptibility patterns: report from the 2002-2003 worldwide Zyvox Annual Appraisal of Potency and Spectrum (ZAAPS) Program. Int J Antimicr Agents 2005; 26: 13-21.
  • Von der Lippe B, Sandven P, Brubakk O. Efficacy and safety of linezolid in multidrug resistand tuberculosis. J Infect 2006; 52: 92-6.
  • Prammananan T, Chaiprasert A, Leechawengwongs M. In vitro activity of linezolid against multidrug-resistant tuberculosis (MDR-TB) and extensively drug-resistant (XDR)-TB isolates. Int J Antimicrob Agents 2009; 33: 190-1.
  • Solak N, Rollas S. Synthesis and antituberculosis activity of 2-(aryl/alkylamino)-5-(4-aminophenyl)-1,3,4-thiadia- zoles and their Shiff bases. ARKIVOC 2006; 12: 173-81.
  • Karakuş S, Çoruh U, Barlas-Durgun B, Vázquez-López EM, Özbaş-Turan S, Akbuğa J, Rollas S. Synthesis and cytotoxic activity of some 1,2,4-triazoline-3-thione and 2,5-disubstituted-1,3,4-thiadiazole derivatives. Marmara Pharm J 2010; 14(2): 84-90.
  • Rollas S, Kokyan Ş, Koçyiğit-Kaymakcıoğlu B, Özbaş- Turan S, Akbuga J. Synthesis and evaluation of cytotoxic activities of some substituted isoxazolone derivatives. Marmara Pharm J 2011; 15: 94-9.
  • Rollas S. Cleavage of azo compounds with hydrazine hydrate and some new 1,3,4-thiadiazole derivatives. J Pharm Univ Mar 1985; 1: 59-68.
  • Rollas S. Reduction of aromatic and heteroaromatic azo compounds with hydrazine hydrate. Marmara Pharm J 2010; 14: 41-6.
  • Özger Y, Rollas S. Reductive cleavage of azo compounds with hydrazine and some 1,3,4-thiadiazole derivatives III. J Pharm Univ Mar 1988; 5: 133-41.
  • Ergenç N, Rollas S The coupling products of aliphatic ac- tive C-H compounds with diazonium salts I. J Fac Pharm Istanbul 1975; 11: 8-23.
  • Collins L, Franzblau SG. Microplate alamar blue assay vesus BACTEC 460 system for high-throughput screen- ing of compoundsagainst Myccbacterium tuberculosis and Myccbacterium avium. Antimicrob Agents Chem- other 1997; 41: 1004-9.
There are 34 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Başak Oral This is me

Sevim Rollas This is me

Publication Date March 7, 2014
Published in Issue Year 2012 Volume: 16 Issue: 3

Cite

APA Oral, B., & Rollas, S. (2014). The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety. Marmara Pharmaceutical Journal, 16(3), 222-228. https://doi.org/10.12991/mpj.61269
AMA Oral B, Rollas S. The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety. J Res Pharm. March 2014;16(3):222-228. doi:10.12991/mpj.61269
Chicago Oral, Başak, and Sevim Rollas. “The Synthesis and Antitubercular Activity of Substituted hydrazone,2-Pyrazoline-5- One and 2-Isoxazoline-5-One Derivatives Possessing 1,3,4-Thiadiazole Moiety”. Marmara Pharmaceutical Journal 16, no. 3 (March 2014): 222-28. https://doi.org/10.12991/mpj.61269.
EndNote Oral B, Rollas S (March 1, 2014) The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety. Marmara Pharmaceutical Journal 16 3 222–228.
IEEE B. Oral and S. Rollas, “The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety”, J Res Pharm, vol. 16, no. 3, pp. 222–228, 2014, doi: 10.12991/mpj.61269.
ISNAD Oral, Başak - Rollas, Sevim. “The Synthesis and Antitubercular Activity of Substituted hydrazone,2-Pyrazoline-5- One and 2-Isoxazoline-5-One Derivatives Possessing 1,3,4-Thiadiazole Moiety”. Marmara Pharmaceutical Journal 16/3 (March 2014), 222-228. https://doi.org/10.12991/mpj.61269.
JAMA Oral B, Rollas S. The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety. J Res Pharm. 2014;16:222–228.
MLA Oral, Başak and Sevim Rollas. “The Synthesis and Antitubercular Activity of Substituted hydrazone,2-Pyrazoline-5- One and 2-Isoxazoline-5-One Derivatives Possessing 1,3,4-Thiadiazole Moiety”. Marmara Pharmaceutical Journal, vol. 16, no. 3, 2014, pp. 222-8, doi:10.12991/mpj.61269.
Vancouver Oral B, Rollas S. The synthesis and antitubercular activity of substituted hydrazone,2-pyrazoline-5- one and 2-isoxazoline-5-one derivatives possessing 1,3,4-thiadiazole moiety. J Res Pharm. 2014;16(3):222-8.

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