Synthesis of isatin , 5 - chloroisatin and their ∆ 2 - 1 , 3 , 4 oxadiazoline derivatives for comparative cytotoxicity study on brine shrimp

Isatin (3a), isatin 3-carbohydrazone (4a), 5-spiro (isatin) 2-(N-acetyl hydrazino) 4-(N-acetyl)-∆2-1,3,4 oxadiazoline (5a), and 5-spiro (isatin) 2-hydrazino∆2-1,3,4 oxadiazoline (6a) had been synthesized from the unsubstituted oximinoacetanilide (2a). 4-Chlorooximinoacetanilide (2b), 5-chloroisatin (3b), 5-chloroisatin 3-carbohydrazone (4b) and 5-spiro (5-chloroisatin) 2-(N-acetyl hydrazino) 4-N-acetyl ∆2-1,3,4 oxadiazoline (5b) compounds had been synthesized from p-chloroaniline. The structures of the products had been characterized from the spectral analysis and comparative cytotoxicity study of them was studied. Article Info Received: 15 December 2006 Accepted: 1 February 2007 Available Online: 3 January 2008 DOI: 10.3329/bjp.v2i1.494 Cite this article: Islam MR, Mohsin M. Synthesis of isatin, 5-chloroisatin and their ∆2-1, 3, 4 oxadiazoline derivatives for comparative cytotoxicity study on brine shrimp. Bangladesh J Pharmacol. 2007; 2: 7-12. Synthesis of isatin, 5-chloroisatin and their ∆2-1, 3, 4 oxadiazoline derivatives for comparative cytotoxicity study on brine shrimp Md. Rabiul Islam and Mohammad Mohsin Department of Chemistry, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh. This work is licensed under a Creative Commons Attribution 4.0 License. You are free to copy, distribute and perform the work. You must attribute the work in the manner specified by the author or licensor. (14.7 mL) with dry oximinoacetanilide (4 g; 0.024 mole) at 70-80°C the solution was cooled to room temperature and poured upon 10-12 times of its volume of crushed ice. The orange red crude solid product of 3a was separated from the solution after half an hour which was filtered, washed well with cold water and dried in a vacuum desiccators. The orange red pure product of 3a was re-crystallized from ethyl acetate having m.p. 180-182°C, yield 2.3 g (65%); Rf 0.4 (PE : EA ; 3 : 2). IR: : 3189 (br,nNH; amide), 3106 (w,nCH, aromatic), 1726 (sh,nC=O, keto), 1614 (sh,nC=O, lactam), 1460 (sh,nC-C, aromatic). 1H-NMR (DMSO-d6): d ppm: 11.02 (s, 1H; NH); 6.90 (d, J=7.8 Hz, 1H, C1-H); 7.12 (t, 1H, C2-H); 7.56 (t, 1H; C3) ( 1 max  cm KBr  8 Bangladesh J Pharmacol 2007; 2: 7-12