α-氟代和α,α-二氟代苯甲磺酰胺的合成：碳酸酐酶的新型抑制剂
Synthesis of alpha-fluoro- and alpha,alpha-difluoro-benzenemethanesulfonamides: new inhibitors of carbonic anhydrase.
作者信息
Blackburn G Michael, Türkmen Hasan
机构信息
University of Sheffield, Department of Chemistry, Sheffield, S3 7HF, England.
出版信息
Org Biomol Chem. 2005 Jan 21;3(2):225-6. doi: 10.1039/b417327a. Epub 2004 Dec 7.
Direct fluorination of arenemethanesulfonamide anions under mild conditions and in high yield has been accomplished using N-fluorobisbenzenesulfonimide, NFSi, on carbanions of N-tert-butyl- and N-bis-(4-methoxyphenyl-methyl)-benzenemethanesulfonamides giving novel alpha-fluoro- and alpha,alpha-difluoro-benzenemethanesulfonamides respectively: IC(50) and pK(a) data show that alpha-halogenation enhances sulfonamide acidity incrementally and correlates well with increased carbonic anhydrase inhibition, while lipophilicity is also enhanced.
在温和条件下，使用N-氟双苯磺酰亚胺（NFSi）对N-叔丁基-和N-双（4-甲氧基苯基甲基）-苯甲磺酰胺的碳负离子进行芳烃甲磺酰胺阴离子的直接氟化反应，分别得到了新型的α-氟-和α,α-二氟-苯甲磺酰胺，产率很高：半数抑制浓度（IC50）和酸度系数（pKa）数据表明，α-卤化可逐步提高磺酰胺的酸度，且与碳酸酐酶抑制作用的增强密切相关，同时亲脂性也有所增强。
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