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Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core

Year 2016, Volume: 20 Issue: 2, 207 - 215, 18.03.2016

Abstract

ABSTRACT

Some novel cyclohexylidenehydrazide derivatives carrying five membered heterocyclic ring, 1,3-thiazole were synthesized to investigate their antiviral (including anti-HIV) activity against diverse DNA and RNA viruses in CRFK, HeLa, HEL, MDCK, Vero and MT4 cell cultures. None of the compounds was active against any of the DNA or RNA viruses at 100 μM.

References

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  • Rauf A, Farshori NN. Microwave-Induced Synthesis of Aromatic Heterocycles, Springer Dordrecht Heidelberg London New York. 2012.
  • De Souza MVN, De Almeida MV. Drug antiHIV: Past, present and future perspectives. Quim Nova, 2003; 26: 366-372.
  • Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, De Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem, 2006; 49: 6819-6832.
  • Rehman MZ, Anwar CJ, Ahmad S. An efficient synthesis of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides. Bull Korean Chem Soc, 2005; 26: 1771-1775.
  • Knadler MP, Bergstrom RF, Callaghan JT, Rubin A. Nizatidine, an H2-blocker. Its metabolism and disposition in man. Drug Metab Dispos, 1986; 14: 175-182.
  • Pasqualotto AC, Thiele KO, Goldani LZ. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr Opin Investig Drugs, 2010; 11: 165-174.
  • Fox LM, Saravolatz LD. Nitazoxanide: a new thiazolide antiparasitic agent. Clin Infect Dis, 2005; 40: 1173-1180.
  • Ayati A, Emami S. Asadipour A, Shafiee A and Foroumadi A. Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery. Eur J Med Chem, 2015; 97: 699-718.
  • Rollas S, Küçükgüzel ŞG. Biological activities of hydrazone derivatives. Molecules, 2007; 12: 1910, 1939.
  • Koruncev D, Babic I, Cvetnic S, Deljac A. Antibacterial and antiviral effects in a series of hydrazides and hydrazones derived from quinoline-2-carboxylic acid. Acta Pharm Jugosl, 1975; 25: 241-246.
  • Morgan LR, Thangaraj K, LeBlanc B, Rodgers A, Wolford LT, Hooper CL, Fan D, Jursic BS. Design, synthesis and anticancer properties of 4,4’-dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues. J Med Chem, 2003; 46: 4552-4563.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Rollas S. Antituberculosis activity of hydrazones derived from 4-fluorobenzoic acid hydrazide. Med Chem Res, 2009; 18: 277-286.
  • Ulusoy N. Synthesis and antituberculosis activity of cycloalkylidenehydrazide and 4- aza-1-thiaspiro[4.5]decan-3-one derivatives of imidazo[2,1-b]thiazole. Arzneim-Forsch/Drug Res, 2002; 52: 565-571.
  • Riberio IG, Silva KCM, Parrini SC, Miranda ALP, Fraga CAM, Barreiro EJ. Synthesis and antinociceptive properties of structurally planned imidazo[1,2-a]pyridine 3-acylarylhydrazone derivatives. Eur J Med Chem, 1998; 33: 225-235.
  • Prakash D, Prasad SM. Synthesis and antibacterial activities of new quinoline 8-thioglycolylhydrazones. J Indian Chem Soc, 1988; 65: 673-675.
  • Johari RB, Nagar R, Sharma RC. Studies on copper (II), nickel (II),cobalt (II) and zinc (II) complexes of acetone salicyloylhydrazone and ethyl methyl ketone salicyloyl hydrazone. Indian J Chem, 1987; 26A: 962-963.
  • Krečmerová M, Holý A, Pohl R, Masojidková M, Andrei G, Naesens L, Neyts J, Balzarini J, De clercq E, Snoeck R. Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine: synthesis and antiviral activity. J Med Chem, 2007; 50(23): 5765-5772.
  • Ceylan Ş, Bayrak H, Demirbaş A, Ülker S, Alpay-Karaoğlu Ş and Demirbaş N. Synthesis of some new hybride molecules containing several azole moieties and investigation of their biological activities. Russ J Bioorg Chem, 2014; 40(3): 314-329.
  • Tatar E, Küçükgüzel ŞG, Karakuş S, De Clercq E, Andrei G, Snoeck R, Pannecouque C, Öktem Okullu S, Ünübol N, Kocagöz T, Kalaycı S and Şahin F. Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents. Marmara Pharm J, 2015; 19: 88-102.
  • Koçyiğit-Kaymakçıoğlu B, Toklu HZ, İkiz S, Bağcıgil AF, Rollas S, Yakut Özgür N and Ak S. Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles. J Enzym Inh Med Chem, 2008; 23(4): 454-461.
  • Somogyi L. Notes on the reactions of ketone acylhydrazones under acylation conditions. Tetrahedron, 41; 1985: 5187-5190.
  • Vicini P, Geronikaki A, Anastasia K, Incerti M and Zani F. Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg Med Chem, 2006; 14: 3859-3864.
  • Göktaş F, Vanderlinden E, Naesens L, Cesur N and Cesur Z. Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives. Bioorg Med Chem, 2012; 20: 7155-7159.
  • Güzel Ö, İlhan E and Salman A. Synthesis and antimycobacterial activity of new 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives. Monats für Chem, 2006; 137: 795-801.
  • SDBS web: http//riodb01.ibase.aist.go.jp/sdbs/cgi-bin/img_disp.cgi spectrum no: 3734HSP-44-755 (Accessed: 10 March 2016).

Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core

Year 2016, Volume: 20 Issue: 2, 207 - 215, 18.03.2016

Abstract

Nuray Ulusoy Güzeldemirci, Erkan Pehlivan, Zeynep Halamoğlu, Ayşe Kocabalkanlı Istanbul University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, 34116 Istanbul, Turkey

References

  • REFERENCES
  • Rauf A, Farshori NN. Microwave-Induced Synthesis of Aromatic Heterocycles, Springer Dordrecht Heidelberg London New York. 2012.
  • De Souza MVN, De Almeida MV. Drug antiHIV: Past, present and future perspectives. Quim Nova, 2003; 26: 366-372.
  • Das J, Chen P, Norris D, Padmanabha R, Lin J, Moquin RV, Shen Z, Cook LS, Doweyko AM, Pitt S, Pang S, Shen DR, Fang Q, De Fex HF, McIntyre KW, Shuster DJ, Gillooly KM, Behnia K, Schieven GL, Wityak J, Barrish JC. 2-Aminothiazole as a novel kinase inhibitor template. Structure-activity relationship studies toward the discovery of n-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl)]-2-methyl-4-pyrimidinyl]amino)]-1,3-thiazole-5-carboxamide (dasatinib, BMS-354825) as a potent pan-Src kinase inhibitor. J Med Chem, 2006; 49: 6819-6832.
  • Rehman MZ, Anwar CJ, Ahmad S. An efficient synthesis of 2-alkyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxides. Bull Korean Chem Soc, 2005; 26: 1771-1775.
  • Knadler MP, Bergstrom RF, Callaghan JT, Rubin A. Nizatidine, an H2-blocker. Its metabolism and disposition in man. Drug Metab Dispos, 1986; 14: 175-182.
  • Pasqualotto AC, Thiele KO, Goldani LZ. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr Opin Investig Drugs, 2010; 11: 165-174.
  • Fox LM, Saravolatz LD. Nitazoxanide: a new thiazolide antiparasitic agent. Clin Infect Dis, 2005; 40: 1173-1180.
  • Ayati A, Emami S. Asadipour A, Shafiee A and Foroumadi A. Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery. Eur J Med Chem, 2015; 97: 699-718.
  • Rollas S, Küçükgüzel ŞG. Biological activities of hydrazone derivatives. Molecules, 2007; 12: 1910, 1939.
  • Koruncev D, Babic I, Cvetnic S, Deljac A. Antibacterial and antiviral effects in a series of hydrazides and hydrazones derived from quinoline-2-carboxylic acid. Acta Pharm Jugosl, 1975; 25: 241-246.
  • Morgan LR, Thangaraj K, LeBlanc B, Rodgers A, Wolford LT, Hooper CL, Fan D, Jursic BS. Design, synthesis and anticancer properties of 4,4’-dihydroxybenzophenone-2,4-dinitrophenylhydrazone and analogues. J Med Chem, 2003; 46: 4552-4563.
  • Koçyiğit-Kaymakçıoğlu B, Oruç E, Unsalan S, Rollas S. Antituberculosis activity of hydrazones derived from 4-fluorobenzoic acid hydrazide. Med Chem Res, 2009; 18: 277-286.
  • Ulusoy N. Synthesis and antituberculosis activity of cycloalkylidenehydrazide and 4- aza-1-thiaspiro[4.5]decan-3-one derivatives of imidazo[2,1-b]thiazole. Arzneim-Forsch/Drug Res, 2002; 52: 565-571.
  • Riberio IG, Silva KCM, Parrini SC, Miranda ALP, Fraga CAM, Barreiro EJ. Synthesis and antinociceptive properties of structurally planned imidazo[1,2-a]pyridine 3-acylarylhydrazone derivatives. Eur J Med Chem, 1998; 33: 225-235.
  • Prakash D, Prasad SM. Synthesis and antibacterial activities of new quinoline 8-thioglycolylhydrazones. J Indian Chem Soc, 1988; 65: 673-675.
  • Johari RB, Nagar R, Sharma RC. Studies on copper (II), nickel (II),cobalt (II) and zinc (II) complexes of acetone salicyloylhydrazone and ethyl methyl ketone salicyloyl hydrazone. Indian J Chem, 1987; 26A: 962-963.
  • Krečmerová M, Holý A, Pohl R, Masojidková M, Andrei G, Naesens L, Neyts J, Balzarini J, De clercq E, Snoeck R. Ester prodrugs of cyclic 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine: synthesis and antiviral activity. J Med Chem, 2007; 50(23): 5765-5772.
  • Ceylan Ş, Bayrak H, Demirbaş A, Ülker S, Alpay-Karaoğlu Ş and Demirbaş N. Synthesis of some new hybride molecules containing several azole moieties and investigation of their biological activities. Russ J Bioorg Chem, 2014; 40(3): 314-329.
  • Tatar E, Küçükgüzel ŞG, Karakuş S, De Clercq E, Andrei G, Snoeck R, Pannecouque C, Öktem Okullu S, Ünübol N, Kocagöz T, Kalaycı S and Şahin F. Synthesis and biological evaluation of some new 1,3,4-thiadiazole and 1,2,4-triazole derivatives from L-methionine as antituberculosis and antiviral agents. Marmara Pharm J, 2015; 19: 88-102.
  • Koçyiğit-Kaymakçıoğlu B, Toklu HZ, İkiz S, Bağcıgil AF, Rollas S, Yakut Özgür N and Ak S. Synthesis and antinociceptive-antimicrobial activities of some new amide derivatives of 3,5-di/-and 1,3,5-trimethylpyrazoles. J Enzym Inh Med Chem, 2008; 23(4): 454-461.
  • Somogyi L. Notes on the reactions of ketone acylhydrazones under acylation conditions. Tetrahedron, 41; 1985: 5187-5190.
  • Vicini P, Geronikaki A, Anastasia K, Incerti M and Zani F. Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones. Bioorg Med Chem, 2006; 14: 3859-3864.
  • Göktaş F, Vanderlinden E, Naesens L, Cesur N and Cesur Z. Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives. Bioorg Med Chem, 2012; 20: 7155-7159.
  • Güzel Ö, İlhan E and Salman A. Synthesis and antimycobacterial activity of new 2-hydroxy-N-(3-oxo-1-thia-4-azaspiro[4.4]non-4-yl)/(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-2,2-diphenylacetamide derivatives. Monats für Chem, 2006; 137: 795-801.
  • SDBS web: http//riodb01.ibase.aist.go.jp/sdbs/cgi-bin/img_disp.cgi spectrum no: 3734HSP-44-755 (Accessed: 10 March 2016).
There are 26 citations in total.

Details

Primary Language English
Journal Section Articles
Authors

Nuray Ulusoy

Erkan Pehlivan This is me

Zeynep Halamoğlu This is me

Ayşe Kocabalkanlı This is me

Publication Date March 18, 2016
Published in Issue Year 2016 Volume: 20 Issue: 2

Cite

APA Ulusoy, N., Pehlivan, E., Halamoğlu, Z., Kocabalkanlı, A. (2016). Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core. Marmara Pharmaceutical Journal, 20(2), 207-215. https://doi.org/10.12991/mpj.20162019913
AMA Ulusoy N, Pehlivan E, Halamoğlu Z, Kocabalkanlı A. Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core. Marmara Pharm J. February 2016;20(2):207-215. doi:10.12991/mpj.20162019913
Chicago Ulusoy, Nuray, Erkan Pehlivan, Zeynep Halamoğlu, and Ayşe Kocabalkanlı. “Synthesis and Antiviral Activity Evaluation of Some New Cyclohexylidenehydrazide Derivatives of 1,3-Thiazole Core”. Marmara Pharmaceutical Journal 20, no. 2 (February 2016): 207-15. https://doi.org/10.12991/mpj.20162019913.
EndNote Ulusoy N, Pehlivan E, Halamoğlu Z, Kocabalkanlı A (February 1, 2016) Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core. Marmara Pharmaceutical Journal 20 2 207–215.
IEEE N. Ulusoy, E. Pehlivan, Z. Halamoğlu, and A. Kocabalkanlı, “Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core”, Marmara Pharm J, vol. 20, no. 2, pp. 207–215, 2016, doi: 10.12991/mpj.20162019913.
ISNAD Ulusoy, Nuray et al. “Synthesis and Antiviral Activity Evaluation of Some New Cyclohexylidenehydrazide Derivatives of 1,3-Thiazole Core”. Marmara Pharmaceutical Journal 20/2 (February 2016), 207-215. https://doi.org/10.12991/mpj.20162019913.
JAMA Ulusoy N, Pehlivan E, Halamoğlu Z, Kocabalkanlı A. Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core. Marmara Pharm J. 2016;20:207–215.
MLA Ulusoy, Nuray et al. “Synthesis and Antiviral Activity Evaluation of Some New Cyclohexylidenehydrazide Derivatives of 1,3-Thiazole Core”. Marmara Pharmaceutical Journal, vol. 20, no. 2, 2016, pp. 207-15, doi:10.12991/mpj.20162019913.
Vancouver Ulusoy N, Pehlivan E, Halamoğlu Z, Kocabalkanlı A. Synthesis and antiviral activity evaluation of some new cyclohexylidenehydrazide derivatives of 1,3-thiazole core. Marmara Pharm J. 2016;20(2):207-15.