Der Pharma Chemica
Journal for Medicinal Chemistry, Pharmaceutical Chemistry and Computational Chemistry


Synthesis, structural study and biological evaluation of pharmacologically important substituted bis-benzothiazole systems

Author(s): Pradip P. Deohate

A series of {4-[4-(6-substituted-benzothiazol-2-yl-amino)-3-nitro-benzyl]-2-nitro-phenyl}-6-substitutedbenzothiazol- 2-yl-amines have been synthesized by oxidative cyclization of 1-{4-[4-(3-aryl thiocarbamido)-3-nitrobenzyl]- 2-nitro-phenyl}-3-aryl thiocarbamides using the solution of bromine in chloroform followed by the basification with dilute ammonium hydroxide solution. Initially 1-{4-[4-(3-aryl thiocarbamido)-3-nitro-benzyl]-2- nitro-phenyl}-3-aryl thiocarbamides were prepared by the interaction of different aryl isothiocyanates with 4,4’- methylene-bis-(2-nitro aniline). The latter was obtained by treating the mixture of 2-nitro aniline and concentrated hydrochloric acid with 3% aqueous formaldehyde followed by neutralization with sodium hydroxide. The acetylation of bis-benzothiazoles afforded di-acetyl derivatives. The structures of synthesized compounds have been established on the basis of chemical transformation, elemental analysis, equivalent weight determination and IR, 1H-NMR spectral studies. The title compounds have been assayed for their biological activity against gram-positive as well as gram-negative microorganisms.

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