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Paper | Regular issue | Vol 106, No. 5, 2023, pp.847-857
Published online, 14th March, 2023
DOI: 10.3987/COM-23-14830
Transnitrosation of Alicyclic N-Nitrosamines Containing Sulfur Atoms in Five- or Six-Membered Rings

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


Nitric oxide (NO) is a cell transmitter produced in vivo. Alicyclic N-nitroso compounds serve as potential NO donors in vivo due to the formation of S-nitrosoglutathione by transnitrosation. In this study, N-nitroso compounds with a thioamide group and endocyclic sulfur atoms in 5- or 6-membered rings were synthesized and the transfer of nitroso group was analyzed. All compounds synthesized exhibited transnitrosation activity under acidic condtions. N-Nitroso-1,3-thiazinane-4-carbothioamide exhibited the highest transnitrosation activity.