Etodolac thiosemicarbazides: A novel class of hepatitis C virus NS5B polymerase inhibitors;Etodolak tiyosemikarbazitleri: Yeni bir sınıf hepatit c virüsü ns5b polimeraz inhibitörleri

Marmara Pharmaceutical Journal

Volumn 17, Issue 2, 2013, Pages 138-146

  Çikla, Pelin ^a   Arora, Payal ^b   Basu, Amartya ^b   Talele, Tanaji T ^c   Kaushik Basu, Neerja ^b   Küçükgüzel, Ş Güniz ^a  

^a MARMARA UNIVERSITY   (Turkey)

^b RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

^c LONG ISLAND UNIVERSITY   (United States)

Author keywords

Etodolac; Hepatit C NS5B polymerase; Pyrano 3,4 b indole; Thiosemicarbazide

Indexed keywords

EID: 84879004365     PISSN: None     EISSN: 13090801     Source Type: Journal    
DOI: 10.12991/201317382     Document Type: Article

References (40)

1. Jones RA. Etodolac (Lodine®): Profile of an established selective COX-2 inhibitor Inflammopharmacology 2001; 9:63-70.
2. Gopalsamy A, Ciszewski GM, Shi M, Park K. Carbazole and cyclopentaindole derivatives to treat infection with hepatitis C virus. 2006; Patent No: US 2006/0063821.
3. LaPorte MG, Draper TL, Miller LE, Blackledge CW, Leister LK, Amparo E, Hussey AR, Young DC, Chunduru SK, Benetatos CA, Rhodes G, Gopalsamy A, Herbertz T, Burns CJ, Condon SM. The discovery and structure-activity relationships of pyrano[3,4-b]indole based inhibitors of hepatitis C virus NS5B polymerase. Bioorg Med Chem Lett 2010; 20:2968-2973.
4. Gopalsamy A, Lim K, Ciszewski G, Park K, Ellingboe JW, Bloom J, Insaf S, Upeslacis J, Mansour TS, Krishna-murthy G, Damarla M, Pyatski Y, Ho D, Howe AY, Or-lowski M, Feld B, O'Connell J. Discovery of pyrano[3,4-b]indoles as potent and selective HCV NS5B polymerase inhibitors. J Med Chem 2004; 47:6603-6608.
5. Durgun BB, Rollas S, Apaydin S, Öztürk R. Synthesis and antimicrobial activity of some new 1-[4-(4-fluorobenzoylamino)-benzoyl]-4-substituted thiosemicarbazides. Drug Metabol Drug Interact 1995; 12: 145-150.
6. Ulusoy N, Ergenç N, Ötük Saniş G. Synthesis, characterizations and antimicrobial evaluation of new 1-acyl-4-substituted thiosemicarbazide and 2,5-disubstituted 1,3,4-thiadiazole derivatives. Acta Pharm Turc 1996; 38:111-116.
7. Doǧan HN, Rollas S, Erdeniz H. Synthesis, structure elucidation and antimicrobial activity of some 3-hydroxy-2-naphthoic acid hydrazide derivatives. Il Farmaco 1998; 53:462-467.
8. Liesen AP, de Aquino TM, Carvalho CS, Lima VT, de Araújo JM, de Lima JG, de Faria AR, de Melo EJ, Alves AJ, Alves EW, Alves AQ, Góes AJ. Synthesis and evaluation of anti-Toxoplasma gondii and antimicrobial activities of thiosemicarbazides, 4-thiazolidinones and 1,3,4-thiadiazoles. Eur J Med Chem 2010; 45:3685-3691.
9. Botros S, Khalil NA, Naguib BH, El-Dash Y. Synthesis and anticonvulsant activity of new phenytoin derivatives. Eur J Med Chem 2012; 60:57-63.
10. Doǧan HN, Duran A, Yemni E. Synthesis and antibacterial activity of 1-(3-hydroxy-2-naphthoyl)-4-substituted thiosemicarbazides. Drug Metabol Drug Interact 1999; 15:187-195.
11. Plech T, Wujec M, Siwek A, Kosikowska U, Malm A. Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophe-nyl moiety. Eur J Med Chem 2011; 46:241-248.
12. Siwek A, Staczek P, Stefahska J. Synthesis and structure-activity relationship studies of 4-arylthiosemicarbazides as topoisomerase IV inhibitors with Gram-positive antibacterial activity. Search for molecular basis of antibacterial activity of thiosemicarbazides. Eur J Med Chem 2011; 46:5717-5726.
13. Kalyoncuoǧlu N, Rollas S, Sür-Altiner D, Yeǧenoǧlu Y, Anǧ O. 1-[p-(Benzoylamino)benzoyl]-4-substituted thiosemicarbazides: synthesis and antibacterial and antifungal activities. Pharmazie 1992; 47:796-797.
14. Rollas S, Karakuş S, Durgun BB, Kiraz M, Erdeniz H. Synthesis and antimicrobial activity of some 1,4-disubsti-tuted thiosemicarbazide and 2,5-disubstituted 1,3,4-thia-diazole derivatives. Il Farmaco 1996; 51:811-814.
15. Terzioǧlu Klip N, Çapan G, Gürsoy A, Uzun M, Satana D. Synthesis, structure, and antifungal evaluation of some novel 1,2,4-triazolylmercaptoacetylthiosemicar-bazide and 1,2,4-triazolylmercaptomethyl-1,3,4-thiadia-zole analogs. J Enzyme Inhib Med Chem 2010; 25:126-131.
16. Cesur Z, Güner H, Ötük G. Synthesis and antimicrobial activity of new imidazo[2,1-b]thiazole derivatives. Eur J Med Chem 1994; 29:981-983.
17. Siwek A, Stefahska J, Dzitko K, Ruszczak A. Antifungal effect of 4-arylthiosemicarbazides against Candida species. Search for molecular basis of antifungal activity of thiosemicarbazide derivatives. J Mol Model 2012; 18:4159-4170.
18. Şahin G, Palaska E, Kelicen P, Demirdamar R, Altinok G. Synthesis of some new 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones and their anti-inflammatory activities. Arznei-mittelforschung 2001; 51:478-484.
19. Rabea SM, El-Koussi NA, Hassan HY, Aboul-Fadl T. Synthesis of 5-phenyl-1-(3-pyridyl)-1H-1,2,4-triazole-3-carboxylic acid derivatives of potential anti-inflammatory activity. Arch Pharm (Weinheim) 2006; 339:32-40.
20. Küçükgüzel ŞG, Kocatepe A, De Clercq E, Şahin F, Gül-lüce M. Synthesis and biological activity of 4-thiazoli-dinones, thiosemicarbazides derived from diflunisal hy-drazide. Eur J Med Chem 2006; 41:353-359.
21. El-Sabbagh OI, Rady HM. Synthesis of new acridines and hydrazones derived from cyclic 3-diketone for cytotoxic and antiviral evaluation. Eur J Med Chem 2009; 44:3680-3686.
22. Xu K, Thornalley PJ. Antitumour activity of sphingoid base adducts of phenethyl isothiocyanate. Bioorg Med Chem Lett 2000; 10:53-54.
23. He J, Wang X, Zhao X, Liang Y, He H, Fu L. Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety. Eur J Med Chem 2012; 54:925-930.
24. Al-Saadi MS, Faidallah HM, Rostom SA. Synthesis and biological evaluation of some 2,4,5-trisubstituted thia-zole derivatives as potential antimicrobial and anticancer agents. Arch Pharm (Weinheim) 2012; 341:424-434.
25. Çikla P, Derya Özsavci D, Bingöl-Özakpinar Ö, Şener A, Çe-vik Ö, Suna Özbaş-Turan S, Akbuǧa J, Şahin F, Küçükgüzel SG. Synthesis, cytotoxicity and pro-apoptosis of etodolac hy-drazide derivatives as anticancer agents. Arch Pharm Chem Life Sci. 2013; in press.
26. Chen Y, Bopda-Waffo A, Basu A, Krishnan R, Silberstein E, Taylor DR, Talele TT, Arora P, Kaushik-Basu N. Characterization of aurintricarboxylic acid as a potent hepatitis C virus replicase inhibitor. Antivir Chem Chemother 2009; 20:19-36.
27. Kaushik-Basu N, Bopda-Waffo A, Talele TT, Basu A, Chen Y, Küçükgüzel ŞG 4-Thiazolidinones: a novel class of hepatitis C virus NS5B polymerase inhibitors. Front Biosci 2008; 13:3857-3868.
28. Kaushik-Basu N, Bopda-Waffo A, Talele TT, Basu A, Costa PR, da Silva AJ, Sarafianos SG, Noel F. Identification and characterization of coumestans as novel HCV NS5B polymerase inhibitors. Nucleic Acids Res 2008; 36:1482-1496.
29. Li H, Tatlock J, Linton A, Gonzalez J, Jewell T, Patel L, Ludlum S, Drowns M, Rahavendran SV, Skor H, Hunter R, Shi ST, Herlihy KJ, Parge H, Hickey M, Yu X, Chau F, Nonomiya J, Lewis C. Discovery of (R)-6-cyclopen-tyl-6-(2-(2,6-diethylpyridin-4-yl)ethyl)-3-((5,7-dime-thyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methyl)-4-hy-droxy-5,6-dihydropyran-2-one (PF-00868554) as a potent and orally available hepatitis C virus polymerase inhibitor. J Med Chem 2009; 52:1255-1258.
30. Rollas S. Bazi{dotless} 1-aroil-4-alkil/ariltiyosemikarbazitler. Doǧa Bilim Dergisi Ti{dotless}p 1983; 7:65-72
31. Palaska E, Şahin G, Kelicen P, Durlu NT, Altinok G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones. Il Farmaco 2002; 57:101-107.
32. Çapan G, Ulusoy N, Ergenç N, Kiraz M New 6-phenylimidazo[2,1-b]thiazole derivates: Synthesis and antifungal activity. Monatsh. für Chemie 1999; 130:1399-1407
33. Küçükgüzel ŞG, Oruç EE, Rollas S, Şahin F, Özbek A. Synthesis, characterisation and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur J Med Chem 2002; 37:197-206.
34. Wujec M, Stefahska J, Siwek A, Tatarczak M. Synthesis, lipophilicity and antimicrobial activity of new derivatives of thiosemicarbazides and 1,2,4-triazoline-5-thione. Acta Pol Pharm 2009; 66:73-82.
35. Tatar E, Küçükgüzel İ, De Clercq, Şahin F, Güllüce M. Synthesis, characterization and screening of antimicrobial, antituberculosis, antiviral and anticancer activity of novel 1,3-thiazolidine-4-ones derived from 1-[2-(benzoylamino)-4-(methylthio)butyryl]-4-alkyl/ arylalkyl thiosemicarbazides. Arkivoc 2008;, 14:191-210.
36. Gürsoy A, Karali N. Synthesis and anticonvulsant activity of new acylthiosemicarbazides and thiazolidones. Il Farmaco 1995; 50:857-866.
37. Abdel-Aziz M, Abdel-Rahman HM Synthesis and anti-my-cobacterial evaluation of some pyrazine-2-carboxylic acid hydrazide derivatives. Eur J Med Chem 2010; 45: 3384-3388
38. Salgn-Gökşen U, Gökhan-Kelekçi N, Göktaş Ö, Köysal Y, Kiliç E, Işik Ş, Aktay G, Özalp M.1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: Synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorg Med Chem 2007; 15:5738-5751.
39. Howe AY, Cheng H, Thompson I, Chunduru SK, Herrmann S, O'Connell J, Agarwal A, Chopra R, Del Vecchio AM Molecular mechanism of a thumb domain hepatitis C virus nonnucleoside RNA-dependent RNA polymerase inhibitor. Antimicrob Agents Chemother 2006; 50:4103-4113.
40. This work was supported by The Scientific and Technical Research Council of Turkey (TÜBİTAK), Research Fund Project Number: SBAG-HYD-339 (108S257) to S.G.K and. the National Institute of Health Research Grant DK066837 to N.K.-B. Etodolac was supplied by Bilim Pharmaceutical Industry