Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide

被引：334

作者：

Küçükgüzel, G ^{[1
]}

Kocatepe, A

De Clercq, E

Sahin, F

Güllüce, M

机构：

[1] Marmara Univ, Fac Pharm, Dept Pharmaceut Chem, TR-34668 Istanbul, Turkey

[2] Katholieke Univ Leuven, Rega Inst Med Res, B-3000 Louvain, Belgium

[3] Yeditepe Univ, Fac Engn & Architecture, Dept Genet & Bioengn, TR-34755 Istanbul, Turkey

[4] Ataturk Univ, Biotechnol Applicat & Res Ctr, TR-25240 Erzurum, Turkey

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2006年 / 41卷 / 03期

关键词：

4-thiazolidinone; anti-HIV activity; diflunisal; thiosemicarbazide;

D O I：

10.1016/j.ejmech.2005.11.005

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two novel series of 4-thiazolidinone derivatives, namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [2-(5-nitro-2-furyl/substituted phenyl)-4-thiazol idinone-3 -y1jam ides (5a-g) and 2-(2',4'-difluoro4-hydroxybipheiiyl-3-carbonylhydrazono)-3-alkyl/ary1-4-thiazolidinones (6ae) together with 5-(2',4'-difluoro4-hydroxybiphenyl-5-yi)-2-cyclohexylamino-1,3,4-oxadiazole (7a) have been synthesized as title compounds. 1-(2',4'-Difluoro-4-hydroxybiphenyl-3-carbonyl)4-alkyl/atylthiosemicarbazides (4a-g) were also obtained and used as intermediate to give the title compounds. All synthesized compounds were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv, antiviral and antimicrobial activities against various virus, bacteria and fungi strains. (c) 2006 Elsevier SAS. All rights reserved.

引用

页码：353 / 359

页数：7

共 30 条

[1] 4-thiazolidinones: Novel inhibitors of the bacterial enzyme MurB [J].

Andres, CJ ;

Bronson, JJ ;

D'Andrea, SV ;

Deshpande, MS ;

Falk, PJ ;

Grant-Young, KA ;

Harte, WE ;

Ho, HT ;

Misco, PF ;

Robertson, JG ;

Stock, D ;

Sun, YX ;

Walsh, AW .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) :715-717

[2]

Ates O, 1997, ARZNEIMITTEL-FORSCH, V47, P1134

[3]

Ates Ö, 2000, ARZNEIMITTEL-FORSCH, V50, P569

[4] Novel inhibitors of an emerging target in Mycobacterium tuberculosis;: Substituted thiazolidinones as inhibitors of dTDP-rhamnose synthesis [J].

Babaoglu, K ;

Page, MA ;

Jones, VC ;

McNeil, MR ;

Dong, CJ ;

Naismith, JH ;

Lee, RE .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (19) :3227-3230

[5]

Barreca Maria Letizia, 2003, Farmaco (Lausanne), V58, P259, DOI 10.1016/S0014-827X(03)00024-7

[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] Synthesis and preliminary evaluation of some pyrazine containing thiazolines and thiazolidinones as antimicrobial agents [J].

Bonde, CG ;

Gaikwad, NJ .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2151-2161

[9]

Bukowski L, 1998, PHARMAZIE, V53, P373

[10] NEW ACYLTHIOSEMICARBAZIDES, THIAZOLIDINONES, AND 1,3,4-OXADIAZOLES AS POSSIBLE ANTICONVULSANTS [J].

CESUR, N ;

CESUR, Z ;

GURSOY, A .

ARCHIV DER PHARMAZIE, 1992, 325 (09) :623-624

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