Synthesis and enantioselective lipase-catalyzed kinetic resolution of methyl 6-(methoxycarbonyl-methyl)sulfanyl-1,4-dihydropyridine-3-carboxylates

被引：6

作者：

Andzans, Z. ^{[1
,2
]}

Krauze, A. ^{[1
]}

Adlere, I. ^{[1
]}

Krasnova, L. ^{[1
]}

Duburs, G. ^{[1
]}

机构：

[1] Latvian Inst Organ Synth, LV-1006 Riga, Latvia

[2] Univ Latvia, LV-1586 Riga, Latvia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2013年 / 49卷 / 03期

关键词：

dihydropyridines; Candida antarctica lipase B; enzymatic kinetic resolution; CALCIUM-CHANNEL BLOCKERS; 1,4-DIHYDROPYRIDINE DERIVATIVES; RATS; DIHYDROPYRIDINES; ANTAGONISTS; MODULATION; SCAFFOLD;

D O I：

10.1007/s10593-013-1263-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of methyl 6-(methoxycarbonylmethyl)sulfanyl-1,4-dihydropyridine-3-carboxylates as more lipophilic derivatives of biologically active 6-methylsulfanyl-1,4-dihydropyridine-3-carboxylic acid esters has been prepared by alkylation of 6-thioxo-1,4-dihydropyridines with methyl bromoacetate. The kinetic resolution catalyzed by Candida antarctica lipase B (Novozym 435(A (R))) has been investigated; the enantiomeric excess of the target products reached 70%. The experiments revealed that the 6-(methoxycarbonylmethyl)sulfanyl group is an essentially new activating group, which, being removed by five bonds from the chiral center, undergoes easy enzymatic hydrolysis and could be used for kinetic resolution of racemic 1,4-dihydropyridines.

引用

页码：421 / 427

页数：7

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