Literature DB >> 19271724

An improved synthesis of (+/-)-N'-nitrosonornicotine 5'-acetate.

Gwendolyn A Marriner1, Sean M Kerwin.   

Abstract

A concise and efficient route to (+/-)-N'-nitrosonornicotine 5'-acetate (NNN-5'-OAc), a stable precursor of the active metabolite 5'-hydroxy(+/-)-N'-nitrosonornicotine NNN-5'-OH is reported. The synthesis utilizes sulfinimine chemistry to give (+/-)-NNN-5'-OAc in 26% yield over 4 steps.

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Year:  2009        PMID: 19271724     DOI: 10.1021/jo9000417

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  2 in total

1.  DNA Adduct Formation from Metabolic 5'-Hydroxylation of the Tobacco-Specific Carcinogen N'-Nitrosonornicotine in Human Enzyme Systems and in Rats.

Authors:  Adam T Zarth; Pramod Upadhyaya; Jing Yang; Stephen S Hecht
Journal:  Chem Res Toxicol       Date:  2016-02-09       Impact factor: 3.739

2.  Identification of an N'-Nitrosonornicotine-Specific Deoxyadenosine Adduct in Rat Liver and Lung DNA.

Authors:  Yupeng Li; Stephen S Hecht
Journal:  Chem Res Toxicol       Date:  2021-03-11       Impact factor: 3.739

  2 in total

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