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Synthesis and Anti-HIV Activity of 4-Chloro-2-mercapto-N-(1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)benzenesulfonamide Derivatives

Pomarnacka E.

Polish Journal of Chemistry

2007

Vol. 81, nr 3

345-352

The synthesis of 4-chloro-2-mercapto-N-(1,5-dimethyl- or 1-alkyl-1,4,5,6-tetrahydro- 1,2,4-triazin-3-yl)benzenesulfonamides 15-28 is described. Suggested mechanism of the investigated reaction is discussed. The compounds 15-17 and 19 were tested for their in vitro anti-HIV potency at the National Cancer Institute and only 4-chloro-2- mercapto-N-(1-methyl-1,4,5,6-tetrahydro-1,2,4-triazin-3-yl)benzenesulfonamide (15) showed reasonable activity (TI50 = 6.21).

Synthesis of N,S-Substituted 4-Chloro-2-mercapto-5-methylbenzenesulfonamide Derivatives as Potential Anti-HIV Agents

Brzozowski Z., Sławiński J.

Polish Journal of Chemistry

2006

Vol. 80, nr 11

1807-1815

A new series of N,S-substituted 4-chloro-2-mercapto-5-methylbenzenesulfonamide derivatives 12-15, 17, 18 and 20-24 have been synthesized as potential anti-HIV agents. All compounds were screened at the National Cancer Institute (Bethesda, USA) for their in vitro anti-HIV-1 activity, and relationships between structure and anti-HIVactivity are discussed. The prominent compounds with remarkable activity were [5-chloro- 4-methyl-2-(1H-pyrrol-1-ylsulfonyl)phenylthio]acetamide 22 (EC50 = 5.9 _M) and 4-bromophenyl 5-chloro-4-methyl-2-(1H-pyrrol-1-ylsulfonyl)phenylthiomethyl ketone 4-phenylsemicarbazone 24 (EC50 = 5.1 mi M).