Parimal M. Chatrabhuji et al./ Elixir Org. Chem. 54A (2013) 12781-12783 12781 Introduction 4- Thiazolidinones are associated with anticancer 1 and versatile pharmacological activities 2,3 like Anti-tubercular 4 Anti– inflammatory 5 antimicrobial 6 , Anti - HIV 7 , antioxidant 8 , etc. Some thiazolidines are reported as analgesic and ulcerogenic 9 . Moreover anils are reported to have significant anticancer 10 and antibacterial 11 activity. All these observations and important role of anils and 4- thiazolidinones in certain biological reactions prompted us to synthesize some 4- Thiazolidinones incorporating styryl moiety and to study their antibacterial activity. 4 - Oxo - thiazolidines are synthesized either by cyclisation of acyclic compounds or by interconversion among appropriately substituted thiazolidinone derivatives by the action of thioglycolic acid on Schiff ’ s bases. The reaction undergoes by the attack of the mercapto acetic acid upon the C = N group, with the - S - CH 2 - COOH adding to the carbon atom followed by the capture of a proton by nitrogen and subsequent cyclisation. 1 – benzylidine – 2 – [(4 – methyl cinnamoyl)] hydrazine on condensation with thiomalic acid gives 4- thiazolidinone-5-acetic acid. The steps involved in the synthesis are shown in scheme 1(Page-8). The constitution of all the products has been characterized using elemental analyses, IR, 1 H NMR and mass spectral study. All the compounds were screened for their in vitro antimicrobial activity against different strains of bacteria. Experimental All the reagents used were of A R grade. Melting point of all the compounds are determined in open capillary tubes and are uncorrected. Thin layer chromatography was used for monitoring the reaction and to check purity. IR spectra recorded on Bio – Rad FTS – 40 spectrophotometer on KBr disc. 1 H NMR spectra were recorded on a model DPX – 200 Brucker FT – NMR instrument using TMS as an internal standard, FAB mass spectra were recorded on JEOL SX 102/DA 6000 spectrophotometer. All the compounds gave satisfactory elemental analysis. PREPARATION OF 2 – PHENYL - 3 - [(4 - METHYL CINNAMOYL AMINO) - 4 - OXO – THIAZOLIDINES-5- ACETIC ACID Different methods for the preparation of 4-thiazolidinone s have been reported 12,13 . Preparation of 1 – benzylidine– 2 – [(4 – methyl cinnamoyl)] hydrazine (Type -III)( Compound3a): 4 – Methyl cinnamoyl hydrazine (1.76 g; 0.01 M) was dissolved in methanol (30 ml) and benzaldehyde (0.92 g; 0.01 M) in methanol (10 ml) was slowly added. The reaction mixture was refluxed for 3 hours on water bath. The resulting mass was allowed to cool at room temperature; product separated was filtered and washed with ice cold methanol, dried and recrystallised from ethanol (95 %). Compound(3a): Yield : 87.12 % ; m.p. : 182 o C; Anal. Calcd. For C 17 H 16 N 2 O : C 72.27; H 6.06; N 10.60 . Found : C 72.10; H 5.96; N 10.50 . IR (KBr, cm -1 ) : 1646 (C=O stretching of cinnamoyl group), 814 (para substituted Pheyl ring), 3221 (N-H stretching) , 1445(C=N stretching), 1375, 2850(C-H sym. and asym. stretching of –CH 3 group). 1 H NMR(200M Hz,DMSO-d 6 , / ppm ): 1.65 (3H , s, Ar - CH 3 ), 8.5 (1H, s, NH ) , 8.7- 7.5 (9H, m, Aromatic protons ) , , 6.4(1H, m, Ar-CH), 2. 26 (2H , dd, - CH = CH -). Preparation of 2–phenyl– 3 – [(4 – methyl cinnamoyl) amino] 4 - oxo – thiazolidine-5-acetic acid(Type-IV) (Compound 4a): To a solution of 1 – benzylidine – 2 – [(4 – methyl cinnamoyl)] hydrazine (2.64 g; 0.01 M) in 1: 4 dioxane (25 ml) was added thiomalic acid (1.6 g; 0.01 M). The mixture was refluxed at 110 – 115 o C for 8 hours. The reaction mixture was allowed to cool at room temperature and triturated with 10 % sodium bicarbonate solution to remove un reacted mercapto acetic acid. The solid product thus separated was filtered and washed with water. Recrystallized from ethanol (95 %). Compound(4a): Yield: 73.23% ; m.p.: 73 o C; m.w.: 396.46 ; Anal. Calcd. For C 21 H 20 N 2 O 4 S ;C 63.62; H 5.04; N 7.06; S, 8.09. Found : C 63.59; H 5.01; N , 7.01 ; S, 8.02. TLC solvent Tele: E-mail addresses: kirankartik@yahoo.com © 2013 Elixir All rights reserved Synthesis and antimicrobial activity of some 4 - oxo – thiazolidines-5-acetic acids Parimal M. Chatrabhuji 1 , Kartik B. Vyas 2 , Kiran S. Nimavat 2 and Navinchandra K. Undavia 1 * 1 Department of Chemistry, Kadi Science College – Kadi (N.G.) Gujarat, India. 2 Department of Chemistry, Government Science College – Gandhinagar-382 015,Gujarat, India. ABSTRACT 4- Oxo- thiazolidines substituted in 2 and 3 positions exhibit a wide range of biological activities. A series of 4-oxo-thiazolidine (4 a-o) have been obtained by cyclisation of various Schiff’s base (3) with thiomalic acid. The Schiff’s bases (3) are obtained by the reaction of 4 – Methyl cinnamoyl hydrazine with appropriate benzaldehyde. The product is characterized by spectral and analytical data. Most of the tested compounds show promising antibacterial activity. © 2013 Elixir All rights reserved. ARTICLE INFO Article history: Received: 14 July 2012; Received in revised form: 15 March 2013; Accepted: 18 March 2013; Keywords Schiff’s base, Thiazolidinones Antibacterial activity. Elixir Org. Chem. 54A (2013) 12781-12783 Organic Chemistry Available online at www.elixirpublishers.com (Elixir International Journal)