Synthesis of carbon‐14 labeled 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone

Andre Castonguay; Stephen S. Hecht

doi:10.1002/jlcr.2580220104

Synthesis of carbon‐14 labeled 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone

Andre Castonguay, Stephen S. Hecht

Laboratory Medicine and Pathology

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

The potent carcinogen 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) is present in tobacco and tobacco smoke. [Carbonyl¹⁴C]NNK (6) was synthesized in 27% overall yield. [Carboxyl‐¹⁴C] nicotinic acid (1) was esterified with benzyl alcohol and the ester 2 was alkylated by 3‐lithio‐N‐methylpyrrolidin‐2‐one (3). The resulting keto‐lactam 4 was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave [carbonyl‐¹⁴C]NNK (6). Carbonyl reduction of [carbonyl‐¹⁴C]NNK with either sodium borohydride or cultured rat liver slices gave [carbinol‐¹⁴C] 4‐(methylnitrosamino)‐1‐(3‐pyridyl) butan‐1‐ol‐(7).

Original language	English (US)
Pages (from-to)	23-28
Number of pages	6
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	22
Issue number	1
DOIs	https://doi.org/10.1002/jlcr.2580220104
State	Published - Jan 1985

Keywords

Carbon‐14 labeled tobacco‐specific N‐nitrosamines

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@article{e9cab39c2d5f4631bdd7337b07ce02d4,

title = "Synthesis of carbon‐14 labeled 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone",

abstract = "The potent carcinogen 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) is present in tobacco and tobacco smoke. [Carbonyl14C]NNK (6) was synthesized in 27% overall yield. [Carboxyl‐14C] nicotinic acid (1) was esterified with benzyl alcohol and the ester 2 was alkylated by 3‐lithio‐N‐methylpyrrolidin‐2‐one (3). The resulting keto‐lactam 4 was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave [carbonyl‐14C]NNK (6). Carbonyl reduction of [carbonyl‐14C]NNK with either sodium borohydride or cultured rat liver slices gave [carbinol‐14C] 4‐(methylnitrosamino)‐1‐(3‐pyridyl) butan‐1‐ol‐(7).",

keywords = "Carbon‐14 labeled tobacco‐specific N‐nitrosamines",

author = "Andre Castonguay and Hecht, {Stephen S.}",

year = "1985",

month = jan,

doi = "10.1002/jlcr.2580220104",

language = "English (US)",

volume = "22",

pages = "23--28",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "John Wiley and Sons Ltd",

number = "1",

}

TY - JOUR

T1 - Synthesis of carbon‐14 labeled 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone

AU - Castonguay, Andre

AU - Hecht, Stephen S.

PY - 1985/1

Y1 - 1985/1

N2 - The potent carcinogen 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) is present in tobacco and tobacco smoke. [Carbonyl14C]NNK (6) was synthesized in 27% overall yield. [Carboxyl‐14C] nicotinic acid (1) was esterified with benzyl alcohol and the ester 2 was alkylated by 3‐lithio‐N‐methylpyrrolidin‐2‐one (3). The resulting keto‐lactam 4 was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave [carbonyl‐14C]NNK (6). Carbonyl reduction of [carbonyl‐14C]NNK with either sodium borohydride or cultured rat liver slices gave [carbinol‐14C] 4‐(methylnitrosamino)‐1‐(3‐pyridyl) butan‐1‐ol‐(7).

AB - The potent carcinogen 4‐(methylnitrosamino)‐1‐(3‐pyridyl)‐1‐butanone (NNK) is present in tobacco and tobacco smoke. [Carbonyl14C]NNK (6) was synthesized in 27% overall yield. [Carboxyl‐14C] nicotinic acid (1) was esterified with benzyl alcohol and the ester 2 was alkylated by 3‐lithio‐N‐methylpyrrolidin‐2‐one (3). The resulting keto‐lactam 4 was hydrolyzed and decarboxylated by treatment with boiling hydrochloric acid. Nitrosation at pH 4.0 gave [carbonyl‐14C]NNK (6). Carbonyl reduction of [carbonyl‐14C]NNK with either sodium borohydride or cultured rat liver slices gave [carbinol‐14C] 4‐(methylnitrosamino)‐1‐(3‐pyridyl) butan‐1‐ol‐(7).

KW - Carbon‐14 labeled tobacco‐specific N‐nitrosamines

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