Synthesis, characterization and antiviral evaluation of 1,3-Thiazolidine-4-one derivatives bearing L-Valine side chain.

被引:10
作者
Tatar, Esra [1 ]
Kucukguzel, Ilkay [1 ]
De Clercq, Erik [2 ]
Krishnan, Ramalingam [3 ]
Kaushik-Basu, Neerja [3 ]
机构
[1] Marmara Univ, Dept Pharmaceut Chem, Fac Pharm, Istanbul, Turkey
[2] Katholieke Univ Leuven, Rega Inst Med Res, Leuven, Belgium
[3] UMDNJ New Jersey Med Sch, Dept Biochem & Mol Biol, Newark, NJ USA
关键词
4-Thiazolidinones; L-valine; anti-HIV activity; anti-HCV activity;
D O I
10.12991/201216397
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
1,3-Thiazolidine-4-ones have been known to possess anti-HIV and anti-HCV activity as they are, respectively, HIV-1 non-nucleoside reverse transcriptase inhibitors and HCV NS5B RNA-dependent RNA- polymerase inhibitors. Some novel 1-[2-(benzoylamino)-3-methylbutyryl]-4-alkyl/arylalkylthiosemicarbazides, 2-[2-(benzoylamino)-3-methylbutyrylhydrazono]-3-alkyl-/arylalkyl-5-nonsubstituted/methyl-1, 3-thiazolidinones, were synthesized and evaluated for their antiviral activity. Antiviral activity of the synthesized compounds were screened against various types of viruses ( Feline Corona Virus ( FIPV), Feline Herpes Virus, HSV- 1(KOS), HSV- 1(TK-KOS ACVr), HSV- 2(G), Vaccinia virus, Vesicular stomatitis virus, Varicella-ZosterVirus TK+VZV, Varicella-ZosterVirus TK-VZV, Cytomegalovirus, Respiratory syncytial virus, Coxsackie B4 virus, Parainfluenza-3 virus, Reovirus-1, Sindbis virus and Punta Toro virus) in CRFK, HEL, HeLa and Vero cell cultures. Anti-HIV and cytotoxicity data were also obtained with the compounds using the strains HIV-1 (IIIB) and HIV-2 ( ROD) in an MT-4/MTT based assay. None of the tested compounds showed antiviral activity at subtoxic concentrations. For all the synthesized compounds anti-HCV NS5B RdRp activity was not observed at the concentration of 100 mu M which was the highest concentration tested.
引用
收藏
页码:181 / 193
页数:13
相关论文
共 53 条
[1]   THE ALPHA-CHYMOTRYPSIN-CATALYZED HYDROLYSIS OF ACETYL-L-VALINE, CHLOROACETYL-L-VALINE AND BENZOYL-L-VALINE METHYL ESTER [J].
APPLEWHITE, TH ;
WAITE, H ;
NIEMANN, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (06) :1465-1469
[2]   Synthesis of newer thiadiazolyl and thiazolidinonyl quinazolin-4(3H)-ones as potential anticonvulsant agents [J].
Archana ;
Srivastava, VK ;
Kumar, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (11) :873-882
[3]   Synthesis and anti-HIV studies of 2-and 3-adamantyl-substituted thiazolidin-4-ones [J].
Balzarini, Jan ;
Orzeszko-Krzesinska, Barbara ;
Maurin, Jan K. ;
Orzeszko, Andrzej .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :303-311
[4]   The role of coinfections in HIV epidemic trajectory and positive prevention: a systematic review and meta-analysis [J].
Barnabas, Ruanne V. ;
Webb, Emily L. ;
Weiss, Helen A. ;
Wasserheit, Judith N. .
AIDS, 2011, 25 (13) :1559-1573
[5]   Computational strategies in discovering novel non-nucleoside inhibitors of HIV-1 RT [J].
Barreca, ML ;
Rao, A ;
De Luca, L ;
Zappalà, L ;
Monforte, AM ;
Maga, G ;
Pannecouque, C ;
Balzarini, J ;
De Clercq, E ;
Chimirri, A ;
Monforte, P .
JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3433-3437
[6]   Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents [J].
Barreca, ML ;
Chimirri, A ;
De Luca, L ;
Monforte, AM ;
Monforte, P ;
Rao, A ;
Zappalà, M ;
Balzarini, J ;
De Clercq, E ;
Pannecouque, C ;
Witvrouw, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (13) :1793-1796
[7]   ISOLATION OF A T-LYMPHOTROPIC RETROVIRUS FROM A PATIENT AT RISK FOR ACQUIRED IMMUNE-DEFICIENCY SYNDROME (AIDS) [J].
BARRESINOUSSI, F ;
CHERMANN, JC ;
REY, F ;
NUGEYRE, MT ;
CHAMARET, S ;
GRUEST, J ;
DAUGUET, C ;
AXLERBLIN, C ;
VEZINETBRUN, F ;
ROUZIOUX, C ;
ROZENBAUM, W ;
MONTAGNIER, L .
SCIENCE, 1983, 220 (4599) :868-871
[8]   Dimerization inhibitors of HIV-1 reverse transcriptase, protease and integrase:: A single mode of inhibition for the three HIV enzymes? [J].
Camarasa, Maria-Jose ;
Velazquez, Sonsoles ;
San-Felix, Ana ;
Perez-Perez, Maria-Jesus ;
Gago, Federico .
ANTIVIRAL RESEARCH, 2006, 71 (2-3) :260-267
[9]   New 6-phenylimidazo[2,1-b]thiazole derivatives:: Synthesis and antifungal activity [J].
Çapan, G ;
Ulusoy, N ;
Ergenç, N ;
Kiraz, M .
MONATSHEFTE FUR CHEMIE, 1999, 130 (11) :1399-1407
[10]   Design, microwave-assisted synthesis and HIV-RT inhibitory activity of 2-(2,6-dihalophenyl)-3-(4,6-dimethyl-5-(un)substituted-pyrimidin-2-yl)thiazolidin-4-ones [J].
Chen, Hua ;
Bai, Jie ;
Jiao, Lingling ;
Guo, Zaihong ;
Yin, Qingmei ;
Li, Xiaoliu .
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (11) :3980-3986