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Paper | Regular issue | Vol 106, No. 2, 2023, pp.305-318
Published online, 21st December, 2022
DOI: 10.3987/COM-22-14788
■ Effect of Sulfur-Containing Side Chains on Transnitrosation of N-Nitroso Compounds of Thiazolidines

Noriko Usui, Masataka Mochizuki, and Keiko Inami*

*Division of Pharmaceutical Organic Chemistry, Faculty of Pharmaceutical Sciences, Sanyo-Onoda City University, Daigakudo-ri 1-1-1, Sanyo-onoda-shi,Yamaguchi, Japan

Abstract

S-Nitrosoglutathione (GSNO) acts as a potential nitric oxide donor in vivo. 3-Nitroso-1,3-thiazolidine-4-thiocarboxamide (1) exhibited a high GSNO- formation activity. In this study, we synthesized novel compounds in which mercaptomethyl (2) or methylthiomethyl (3) group was incorporated into the thiazolidine skeleton instead of a thioamide group. Pseudo-first-order rate constants for GSNO formation for the reaction between the compounds and glutathione followed the order 1>>2≒3. Introduction of another substituent containing a sulfur atom into the thioamide group this time resulted in a decrease in transnitrosation activity. These differences in activity suggested that compounds 2 and 3 transnitrate via a different reaction pathway than 1.