Synthesis and Antiviral Activity of 5‑(4‑Chlorophenyl)-1,3,4-Thiadiazole Sulfonamides

Abstract

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 antitobacco mosaic virus activity.

Structural and vibrational studies on 1-(5-methyl-[1,3,4] thiadiazol-2-yl)-pyrolidin-2-ol

“…The bands in the ranges 1299-1350 cm -1 (Raman bands), 1237-1270 cm -1 (FT-IR gas phase) and 939-1035 cm -1 (FT-IR gas phase) were assigned to CH 2 wagging, CH 2 twisting and CH 2 rocking vibrations, respectively[61]. Based on the above literature data, in this study, the harmonic wavenumbers 1480, 1457, 1439 cm -1 (mode nos:[14][15][16] with >90% TED are assigned to CH 2 scissoring mode of MTPN . Mode no: 16 show good correlation with recorded (1442cm -1 : FT-IR/1445 cm -1 : FT-Raman) spectral data.…”

“…The synthesis of novel thiadiazole derivatives and investigation of their chemical and biological behavior have gained more importance in recent decades. During recent years, an intense investigation of different classes of thiadiazole compounds in many of which are known to possess vast biological properties such as antimicrobial [1], antituberculosis [2,3], anti-inflammatory [4,5], analgesic [6], anticonvulsant [7], antihypertensive [8], antioxidant [9] anticancer [10,11], antifungal [12,13], antiviral [14], antidepressant [15], antibacterial [16][17][18] and antitumour [19]. Thiadiazole become very important compound in medicine, agriculture, and many fields of technology.…”

Synthesis and pro-apoptotic effects of new sulfonamide derivatives via activating p38/ERK phosphorylation in cancer cells

“…In recent times, there has been an increase in studies regarding the substances containing sulfonamide fragment because of their potential applications such as for coordination chemistry 18 , medicinal chemistry 19 , catalyst chemistry 20 , chemical luminescence 21 and analytical chemistry fields 22 . On the other hand, sulfonamide compounds are known to contain inherent pharmacological properties such as antimicrobial 23 , anti-inflammatory 24 , anti-viral 25 , anti-proliferative 26 , angiogenesis 27 and enzyme inhibitory (carbonic anhydrase) activities 28 . Therefore, based on these findings, sulfonamide compounds were synthesized by the reaction of sulfonamide fragments; N-(2-amino-5-benzoylphenyl)-4-nitrobenzenesulfonamide hydrochloride (1), N-(quinolin-8-yl)-4-nitro-benzenesulfonamide hydrochloride (2), N-(pyridine-2-ylmethyl)-4-nitro-benzenesulfonamide hydrochloride (3) with3,4-diaminobenzophenone, 8-aminoquinoline or 2-picoylamine and 4-nitrobenzensulfonyl chloride, respectively and we tested the effects compounds on cell viability, pro-apoptotic gene expression and of p38/ERK activation.…”

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“…[9,10] Sulfonamides represent an important class of medically important compound, which is present in a number of biologically active molecules. In addition, sulfonamide derivatives are extensively used as antitumor, [11,12] antiviral, [13] antimalarial, [14,15] anti-inflammatory, [16] anticancer, [17] anti-carbonic anhydrase, [18] antidiabetic agents, [19] and in Alzheimer's diseases. [20] Computer-aided structure-based rational drug designing have the potential not only of speeding up the drug discovery process thus reducing the costs, but also of changing the way drugs are designed.…”