Synthesis and antimicrobial evaluation of some new fluorinated spiro[[1,5]-benzothiazepin-2,3′[3′H]-indol]-2′(1′H)-ones

A series of fluorinated spiro [1,5-benzothiazepin-2,3'[3'H] -indol]-2'(1'H)-ones have been prepared by the reaction of 2-aminobenzenethiols with 1,3-dihydro-3- [2-phenyl/(4-fluorophenyl)-2-oxoethylidene)-indol-2(1H)-ones (I) under microwave irradiation in open vessels using ethylene glycol as energy transfer medium and thermally in absolute ethanol saturated with hydrogen chloride gas. The comparative studies indicated that the microwave assisted organic synthesis has advantages of significantly reduced reaction time, improved yields and cleaner reactions as compared to the conventional method. All synthesized compounds have been characterized by analytical and spectral data and were screened for their antifungal activity against Alternaria alternata and Fusarium oxysporium and antitubercular activity against Mycobacterium tuberculosis IVb (R=F, X = F) and IVe (R=F, X = CH,) have shown above 90% inhibition in reducing fungal growth of A. alternata while IVa (R=H, X=F) has shown 98% antitubercular activity on primary screening. (C) 1998 Published by Elsevier Science S.A. All rights reserved.