对4-氨基甲基恶唑-5(4H)- 1的亲核攻击，青霉素致癌性的合理化

Journal of The Chemical Society B: Physical Organic Pub Date : 1971-01-01 DOI:10.1039/J29710000848

J. Longridge, D. Timms

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引用次数: 4

摘要

4-氨基甲基恶唑-5(4H)- 1在侧链上的亚甲基碳而不是环羰基上受到亲核攻击。以前报道的青霉素酸只在羰基上反应，当巯基的分子内亲核攻击被抑制时，遵循这种一般模式，这一反应在青霉素致癌性中可能很重要。

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Nucleophilic attack on 4-aminomethyleneoxazol-5(4H)-ones, a rationalisation of penicillin carcinogenicity

4-Aminomethyleneoxazol-5(4H)-ones are shown to undergo nucleophilic attack at the methylene carbon on the side chain rather than at the ring carbonyl group. Penicillenic acid, formerly reported to react exclusively at the carbonyl, follows this general pattern when intramolecular nucleophilic attack by the thiol group is inhibited, a reaction of possible importance in penicillin carcinogenicity.

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Journal of The Chemical Society B: Physical Organic

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