@article{oai:repo.qst.go.jp:00048526,
 author = {Inami, Keiko and Ono, Yuta and Kondo, Sonoe and Nakanishi, Ikuo and Ohkubo, Kei and Fukuzumi, Shunichi and Mochizuki, Masataka and 稲見 圭子 and 中西 郁夫 and 大久保 敬},
 issue = {20},
 journal = {Bioorganic & Medicinal Chemistry},
 month = {Sep},
 note = {S-Nitrosoglutathione (GSNO) relaxes vascular smooth muscles, prevents platelet aggregation, and acts as a potential in vivo nitric oxide donor.  3-Nitroso-1,3-thiazolidine- 4-thiocarboxamide (1), a N-nitrosothioproline analogue, exhibited a high GSNO formation activity.  In this study, two compounds (2 and 3) based on compound 1 were newly synthesized by introducing either one or two methyl groups onto a nitrogen atom on the thioamide substituent in 1.  The pseudo-first-order rate constants (kobs) for the GSNO formation for the reaction between the compound and glutathione (GSH) followed the orde 1 > 2 ≈ 3.  Thus, the introduction of a methyl group(s) onto the thioamide group led to a decrease in the transnitrosation activity.  On the basis of density functional theoretical calculations, the transnitrosation for the N-nitrosothiazolidine thiocarboxamides was proposed to proceed via a bridged intermediate pathway.  Specifically, the protonated compound 1 forms a bridged structure between the nitrogen atom in the nitroso group and two sulphur atoms–one in the ring and the other in the substituent.  The bridged intermediate gives rise to a second intermediate, in which the nitroso group is bonded to the sulphur atom in the thioamide group.  Finally, the nitroso group is transferred to GSH to form GSNO.},
 pages = {6733--6739},
 title = {Effect of Alkyl Group on Transnitrosation of N-Nitrosothiazolidine Thiocarboxamides},
 volume = {23},
 year = {2015}
}