Abstract
Starting from 4-chlorobenzoic acid, 10 new 5-(4-chlorophenyl)-N-substituted-N-1,3,4-thiadiazole-2-sulfonamide derivatives were synthesized in six-steps. Esterification of 4-chlorobenzoic acid with methanol and subsequent hydrazination, salt formation and cyclization afforded 5-(4-chlorophen-yl)-1,3,4-thiadiazole-2-thiol (5). Conversion of this intermediate into sulfonyl chloride 6, followed by nucleophilic attack of the amines gave the title sulfonamides 7a-7j whose structures were confirmed by NMR, IR and elemental analysis. The bioassay tests showed that compounds 7b and 7i possessed certain anti-tobacco mosaic virus activity.
Highlights
Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities [1,2,3]
We synthesized a series of 2-alkylthio-5-(3,4,5-trimethoxyphenyl)-1,3,4thiadiazole derivatives to inhibit the growth of tumor cells [12]
We obtained some chiral thioureas and α-aminophosphonates, cyanoacrylates and certain heterocyclic compounds with the aim of protecting tobacco plants affected with tobacco mosaic virus (TMV), but barring a few exceptional cases, these compounds did not reveal the expected anti-TMV activity [13]
Summary
Sulfonamide drugs which have brought about an antibiotic revolution in medicine are associated with a wide range of biological activities [1,2,3]. Sulfonamide derivatives have been reported to possess antifungal [4,5,6] and herbicidal [7] properties for potential agricultural applications. Certain 1,3,4-thiadiazoles prepared by different groups have often displayed other interesting bioactivities, e.g. anticonvulsant [8], antifungal and antibacterial properties [9,10,11]. Since the incorporation of sulfonamides into 1,3,4-thiadiazole rings can produce compounds that can act as carbonic anhydrase inhibitors [3], we have combined the two pharmacophoric units into one structure to generate new compounds with potential plant anti-viral activities. In the present investigation, 10 novel sulfonamide derivatives containing 1,3,4-thiadiazole rings were synthesized and screened for their anti-TMV activities. Compounds 7b and 7i exhibited approximately 50% TMV inhibition, in the same range as that displayed by the commercial antifungal ningnanmycin
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