Chemoenzymatic synthesis of (S) and (R)-propranolol and sotalol employing one-pot lipase resolution protocol

被引：26

作者：

Kamal, A ^{[1
]}

Sandbhor, M ^{[1
]}

Shaik, AA ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem, Biotransformat Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2004年 / 14卷 / 17期

关键词：

propranolol; sotalol; one-pot lipase resolution;

D O I：

10.1016/j.bmcl.2004.05.084

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Synthesis of both enantiomers of biologically active propranolol and sotalol has been achieved in high optical purity by one-pot reduction of 3 and 7 followed by in situ lipase resolution of the respective chlorohydrins. Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) provided the chlorohydrin and acetate, which on nucleophilic substitution with isopropyl amine afforded the target amino alcohols in high enantio selectivity under mild reaction conditions. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：4581 / 4583

页数：3

相关论文

共 35 条

[1] CLINICAL EXPERIENCES WITH PROPRANOLOL [J].

BESTERMAN, EM ;

FRIEDLANDER, DH .

POSTGRADUATE MEDICAL JOURNAL, 1965, 41 (479) :526-+

[2] PRACTICAL CHEMOENZYMATIC SYNTHESIS OF BOTH ENANTIOMERS OF PROPRANOLOL [J].

BEVINAKATTI, HS ;

BANERJI, AA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5372-5375

[3] Asymmetric synthesis of the antiarrhythmia agent d-sotalol [J].

Brodfuehrer, PR ;

Smith, P ;

Dillon, JL ;

Vemishetti, P .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1997, 1 (02) :176-178

[4] ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION [J].

CHINCHILLA, R ;

NAJERA, C ;

SANCHEZAGULLO, P .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1393-1402

[5] Kinetic resolution of propranolol by a lipase-catalyzed N-acetylation [J].

Chiou, TW ;

Chang, CC ;

Lai, CT ;

Tai, DF .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (04) :433-436

[6] THE SYNTHESIS AND POTASSIUM CHANNEL BLOCKING ACTIVITY OF SOME (4-METHANESULFONAMIDOPHENOXY)PROPANOLAMINES AS POTENTIAL CLASS-III ANTIARRHYTHMIC AGENTS [J].

CONNORS, SP ;

DENNIS, PD ;

GILL, EW ;

TERRAR, DA .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) :1570-1577

[7]

Damle SV, 1999, SYNTHETIC COMMUN, V29, P3855

[8] CHROMATOGRAPHIC RESOLUTION OF 1,2-AMINO ALCOHOLS ON A CHIRAL STATIONARY PHASE CONTAINING N,N'-(3,5-DINITROBENZOYL)-TRANS-1,2-DIAMINOCYCLOHEXANE - THEORETICAL AND PRACTICAL ASPECTS [J].

GASPARRINI, F ;

MISITI, D ;

VILLANI, C ;

LATORRE, F .

JOURNAL OF CHROMATOGRAPHY, 1991, 539 (01) :25-36

[9] RESOLUTION OF THE ENANTIOMERS OF DRUGS CONTAINING AMINO ALCOHOL STRUCTURE AFTER DERIVATIZATION WITH BROMOACETIC ACID [J].

GUBITZ, G ;

PIERER, B ;

WENDELIN, W .

CHIRALITY, 1992, 4 (05) :333-337

[10]

HANDSON RM, 1991, CHEM REV, V91, P437

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