Synthesis of Novel Highly Functionalized 4-Thiazolidinone Derivatives from 4-Phenyl-3-thiosemicarbazones

被引：32

作者：

Benmohammed, Abdelmadjid ^{[1
,2
]}

Khoumeri, Omar ^{[3
]}

Djafri, Ayada ^{[1
]}

Terme, Thierry ^{[3
]}

Vanelle, Patrice ^{[3
]}

机构：

[1] Univ Oran, Lab Synth Organ Appl, Dept Chim, Fac Sci Exactes & Appl, Oran 31000, Algeria

[2] Univ Mascara, Dept Sci & Tech, Fac Sci & Technol, Mascara 29000, Algeria

[3] Aix Marseille Univ, ICR, UMR CNRS 7273, Lab Pharmacochim Radicalaire,Fac Pharm, F-13385 Marseille 05, France

来源：

MOLECULES | 2014年 / 19卷 / 03期

关键词：

4-phenyl-3-thiosemicarbazones; thiazolidinones derivatives; ethyl; 2-bromoacetate; diethyl acetylenedicarboxylate; THIOSEMICARBAZONES; INHIBITORS; SERIES;

D O I：

10.3390/molecules19033068

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We present herein the synthesis in good yields of two series of highly functionalized thiazolidinone derivatives from the reactions of various 4-phenyl-3-thio-semicarbazones with ethyl 2-bromoacetate and diethyl acetylenedicarboxylate, respectively.

引用

页码：3068 / 3083

页数：16

共 26 条

[1]

Agrawal Vijay K., 2000, Acta Pharmaceutica (Zagreb), V50, P281

[2] In vitro activity and mechanism of action against the protozoan parasite Trypanosoma cruzi of 5-nitrofuryl containing thiosemicarbazones [J].

Aguirre, G ;

Boiani, L ;

Cerecetto, H ;

Fernández, M ;

González, M ;

Denicola, A ;

Otero, L ;

Gambino, D ;

Rigol, C ;

Olea-Azar, C ;

Faundez, M .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (18) :4885-4893

[3] Functionalization of 6-nitrobenzo[1,3]dioxole with carbonyl compounds via TDAE methodology [J].

Amiri-Attou, O ;

Terme, T ;

Vanelle, P .

MOLECULES, 2005, 10 (3-5) :545-551

[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]

Bhat MA, 2008, INDIAN J HETEROCY CH, V17, P287

[6] Lowering of 5-nitroimidazole's mutagenicity: Towards optimal antiparasitic pharmacophore [J].

Crozet, Maxime D. ;

Botta, Celine ;

Gasquet, Monique ;

Curti, Christophe ;

Remusat, Vincent ;

Hutter, Sebastien ;

Chapelle, Olivier ;

Azas, Nadine ;

De Meo, Michel ;

Vanelle, Patrice .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (02) :653-659

[7] SRN1 REACTIONS IN THE HETEROCYCLIC SERIES .4. REACTIVITY OF 2,2-DIMETHYL-5-NITRO-1,3-DIOXANE SALTS [J].

CROZET, MP ;

ARCHIAMBAULT, G ;

VANELLE, P ;

NOUGUIER, R .

TETRAHEDRON LETTERS, 1985, 26 (42) :5133-5134

[8] Synthesis, anti-Toxoplasma gondii and antimicrobial activities of benzaldehyde 4-phenyl-3-thiosemicarbazones and 2-[(phenylmethylene)hydrazonol-4-oxo-3-phenyl-5-thiazolidineacetic acids [J].

de Aquino, Thiago M. ;

Liesen, Andre P. ;

da Silva, Rosa E. A. ;

Lima, Vania T. ;

Carvalho, Cristiane S. ;

de Faria, Antnio R. ;

de Araujo, Janete M. ;

de Lima, Jose G. ;

Alves, Antonio J. ;

de Melo, Edesio J. T. ;

Goes, Alexandre J. S. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (01) :446-456

[9] Synthesis and structure-activity relationships of 2-(substituted phenyl)-3-[3-(N,N-dimethylamino)propyl]-1,3-thiazolidin-4-ones acting as H1-histamine antagonists [J].

Diurno, MV ;

Mazzoni, O ;

Correale, G ;

Monterrey, IG ;

Calignano, A ;

La Rana, G ;

Bolognese, A .

FARMACO, 1999, 54 (09) :579-583

[10] Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain [J].

Du, XH ;

Guo, C ;

Hansell, E ;

Doyle, PS ;

Caffrey, CR ;

Holler, TP ;

McKerrow, JH ;

Cohen, FE .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (13) :2695-2707

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