A new method for the preparation of 5-acylidene and 5-imino substituted rhodanine derivatives and their antioxidant and antimicrobial activities

被引：29

作者：

Ungoren, Sevket Hakan ^{[1
]}

Albayrak, Sevil ^{[2
]}

Gunay, Ahmet ^{[1
]}

Yurtseven, Lutfiye ^{[2
]}

Yurttas, Nurgul ^{[1
]}

机构：

[1] Bozok Univ, Fac Arts & Sci, Dept Chem, Yozgat, Turkey

[2] Erciyes Univ, Fac Sci, Dept Biol, Kayseri, Turkey

来源：

TETRAHEDRON | 2015年 / 71卷 / 25期

关键词：

Rhodanines; Wittig reaction; Chalcones; Perimidines; Antioxidant activity; Antimicrobial activity; INHIBITORS; DESIGN; ACIDS;

D O I：

10.1016/j.tet.2015.04.069

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Versatile syntheses of 5-imino or 5-acylidene substituted 1,3-thiazolidin-4-one derivatives are reported from alpha-dioxothiazole systems and phosphoranes via Wittig reactions. Antimicrobial and antioxidant activity of the compounds were evaluated. 5-Carbonylmethylene substituted 2-thioxo-1,3-thiazolidines have better antioxidant properties than the 5-arylimino substituted ones. The % inhibition value of the compound 3 (90.8%) was near to that of standard BHT (93.6%) at the same concentration. Compounds 5 and 15, which have the alkyliden-amide group at the C-5 position of the 1,3-thiazolidine ring showed the highest antimicrobial activities among the synthesized compounds. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：4312 / 4323

页数：12

共 29 条

[1]

Acheson R. M., 1981, J CHEM SOC P1, V2, P415

[2] A simple and effective approach to the synthesis of rhodanine derivatives via three-component reactions in water [J].

Alizadeh, Abdolati ;

Rostamnia, Sadegh ;

Zohreh, Nasrin ;

Hosseinpour, Reza .

TETRAHEDRON LETTERS, 2009, 50 (14) :1533-1535

[3] An efficient solvent-tuning approach for the rapid synthesis of thiazolidinone derivatives and the selective synthesis of 2-amino-4H-1,3-thiazin-4-one and dimethyl 3,3′-thiodiacrylates [J].

Choudhary, Garima ;

Peddinti, Rama Krishna .

TETRAHEDRON LETTERS, 2014, 55 (41) :5597-5600

[4]

Delower M., 2010, OPT MATER, V32, P669

[5] MECHANISM OF INHIBITION OF HISTIDINE DECARBOXYLASE BY RHODANINES [J].

FREE, CA ;

MAJCHROWICZ, E ;

HESS, SM .

BIOCHEMICAL PHARMACOLOGY, 1971, 20 (07) :1421-+

[6] Rhodanine carboxylic acids as novel inhibitors of histone acetyltransferases [J].

Furdas, Silviya D. ;

Shekfeh, Suhaib ;

Kannan, Srinivasaraghavan ;

Sippl, Wolfgang ;

Jung, Manfred .

MEDCHEMCOMM, 2012, 3 (03) :305-311

[7] The synthesis and SAR of rhodanines as novel class C β-lactamase inhibitors [J].

Grant, EB ;

Guiadeen, D ;

Baum, EZ ;

Foleno, BD ;

Jin, HY ;

Montenegro, DA ;

Nelson, EA ;

Bush, K ;

Hlasta, DJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (19) :2179-2182

[8] 2-Thioxothiazolidin-4-one (Rhodanine) [J].

Hajibabaei, Khadijeh .

SYNLETT, 2014, 25 (14) :2083-2084

[9] ALDOSE REDUCTASE INHIBITORS - A POTENTIAL NEW CLASS OF AGENTS FOR THE PHARMACOLOGICAL CONTROL OF CERTAIN DIABETIC COMPLICATIONS [J].

KADOR, PF ;

KINOSHITA, JH ;

SHARPLESS, NE .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (07) :841-849

[10]

Koca I., 2013, HETEROCYCL CHEM, V51, P212

← 1 2 3 →