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Effect of alkyl group on transnitrosation of N-nitrosothiazolidine thiocarboxamides

Title
Effect of alkyl group on transnitrosation of N-nitrosothiazolidine thiocarboxamides
Authors
Inami, KeikoOno, YutaKondo, SonoeNakanishi, IkuoOhkubo, KeiFukuzumi, ShunichiMochizuki, Masataka
Ewha Authors
Shunichi FukuzumiKei Okubo
SCOPUS Author ID
Shunichi Fukuzumiscopus; Kei Okuboscopus
Issue Date
2015
Journal Title
BIOORGANIC & MEDICINAL CHEMISTRY
ISSN
0968-0896JCR Link1464-3391JCR Link
Citation
vol. 23, no. 20, pp. 6733 - 6739
Keywords
S-NitrosoglutathioneTransnitrosationN-Nitrosothioproline1,3-ThiazolidineThiocarboxamide
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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 (k(obs)) for the GSNO formation for the reaction between the compound and glutathione followed the order 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 sulfur 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 sulfur atom in the thioamide group. Finally, the nitroso group is transferred to GSH to form GSNO. (c) 2015 Elsevier Ltd. All rights reserved.
DOI
10.1016/j.bmc.2015.09.008
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자연과학대학 > 화학·나노과학전공 > Journal papers
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