LIPASE-CATALYZED ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE MEPHOBARBITAL, HEXOBARBITAL AND FEBARBAMATE

被引：9

作者：

MURATA, M ^{[1
]}

UCHIDA, H ^{[1
]}

ACHIWA, K ^{[1
]}

机构：

[1] UNIV SHIZUOKA, SCH PHARMACEUT SCI, 395 YADA, SHIZUOKA 422, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 10期

关键词：

LIPASE; HYDROLYSIS; ORGANIC SOLVENT; ASYMMETRIC SYNTHESIS; N-ACYLOXYMETHYL GROUP; CHIRAL BARBITURATE; MEPHOBARBITAL; HEXOBARBITAL; FEBARBAMATE;

D O I：

10.1248/cpb.40.2605

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chiral 5,5-disubstituted N-acyloxymethylbarbiturates have been obtained in 40-99% optical yields by lipase-catalyzed hydrolyses of 5,5-disubstituted N,N'-bisacyloxymethylbarbiturates in H2O-saturated diisopropyl ether. These chiral barbiturates were readily converted into chiral drugs, mephobarbital, hexobarbital and febarbamate.

引用

页码：2605 / 2609

页数：5

共 31 条

[1] PHARMACOKINETICS OF (+)-HEXOBARBITONE, (-)-HEXOBARBITONE AND (+-]-HEXOBARBITONE IN MAN AFTER ORAL ADMINISTRATION
BREIMER, DD
VANROSSU.JM
[J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1973, 25 (09) : 762 - 764
[2] COMPARISON OF DISTRIBUTION NARCOTIC ACTIVITY AND METABOLIC ELIMINATION OF OPTICAL ANTIPODES OF METHYLPHENOBARBITAL
BUCH, H
BUZELLO, W
NEUROHR, O
RUMMEL, W
[J]. BIOCHEMICAL PHARMACOLOGY, 1968, 17 (12) : 2391 - &
[3] GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES
CHEN, CS
SIH, CJ
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06): : 695 - 707
[4] CROUT DHG, 1989, MOD SYN MET, V5, P1
[5] PHARMACODYNAMIC AND PHARMACOKINETIC DIFFERENCES BETWEEN DRUG ENANTIOMERS IN HUMANS - AN OVERVIEW
DRAYER, DE
[J]. CLINICAL PHARMACOLOGY & THERAPEUTICS, 1986, 40 (02) : 125 - 133
[6] ACYLOXYMETHYL AS AN ACTIVATING GROUP IN LIPASE-CATALYZED ENANTIOSELECTIVE HYDROLYSIS - A VERSATILE APPROACH TO CHIRAL 4-ARYL-1,4-DIHYDRO-2,6-DIMETHYL-3,5-PYRIDINEDICARBOXYLATES
EBIIKE, H
TERAO, Y
ACHIWA, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (41) : 5805 - 5808
[7] GOLDAUBERT P, 1961, HELV CHIM ACTA, V44, P1050
[8] MECHANISM OF ACTION OF BARBITURATES
HO, IK
HARRIS, RA
[J]. ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY, 1981, 21 : 83 - 111
[9] ENZYMES IN ORGANIC-SYNTHESIS
JONES, JB
[J]. TETRAHEDRON, 1986, 42 (13) : 3351 - 3403
[10] ASYMMETRIC TRANSFORMATIONS CATALYZED BY ENZYMES IN ORGANIC-SOLVENTS
KLIBANOV, AM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1990, 23 (04) : 114 - 120

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