THE SYNTHESIS OF A CONFORMATIONALLY RIGID CALCIUM-CHANNEL BLOCKER

被引：4

作者：

BARRISH, JC ^{[1
]}

SPERGEL, SH ^{[1
]}

MORELAND, S ^{[1
]}

HEDBERG, SA ^{[1
]}

机构：

[1] BRISTOL MYERS SQUIBB PHARMACEUT RES INST,DEPT PHARMACOL,PRINCETON,NJ 08543

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1992年 / 2卷 / 01期

关键词：

D O I：

10.1016/S0960-894X(00)80664-2

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The preparation of (+/-)-3 and 4, conformationally rigid calcium channel blockers related to diltiazem, is described starting from the known bicyclic ketone 5. The syntheses include the addition of an aryl organometallic reagent to the ketones 9 and 13a respectively, which occurs with unexpected pi-facial selectivity.

引用

页码：95 / 98

页数：4

共 14 条

[1] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF NOVEL CALCIUM-CHANNEL BLOCKERS - 2,5-DIHYDRO-4-METHYL-2-PHENYL-1,5-BENZOTHIAZEPINE-3-CARBOXYLIC ACID-ESTERS AND 2,5-DIHYDRO-4-METHYL-2-PHENYL-1,5-BENZODIAZEPINE-3-CARBOXYLIC ACID-ESTERS [J].

ATWAL, KS ;

BERGEY, JL ;

HEDBERG, A ;

MORELAND, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (04) :635-640

[2]

DAS J, IN PRESS J MED CHEM

[3] SYNTHESIS OF BENZAZEPINONE AND 3-METHYLBENZOTHIAZEPINONE ANALOGS OF DILTIAZEM [J].

FLOYD, DM ;

MOQUIN, RV ;

ATWAL, KS ;

AHMED, SZ ;

SPERGEL, SH ;

GOUGOUTAS, JZ ;

MALLEY, MF .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) :5572-5579

[4]

FLOYD DM, IN PRESS J MED CHEM

[5]

GODFRAIND T, 1986, PHARMACOL REV, V38, P321

[6] CHEMICAL MECHANISMS OF CATALYSIS BY CYTOCHROMES-P-450 - A UNIFIED VIEW [J].

GUENGERICH, FP ;

MACDONALD, TL .

ACCOUNTS OF CHEMICAL RESEARCH, 1984, 17 (01) :9-16

[7] ORGANOCERIUM REAGENTS - NUCLEOPHILIC-ADDITION TO EASILY ENOLIZABLE KETONES [J].

IMAMOTO, T ;

SUGIURA, Y ;

TAKIYAMA, N .

TETRAHEDRON LETTERS, 1984, 25 (38) :4233-4236

[8] CERIUM CHLORIDE-PROMOTED NUCLEOPHILIC-ADDITION OF GRIGNARD-REAGENTS TO KETONES AN EFFICIENT METHOD FOR THE SYNTHESIS OF TERTIARY ALCOHOLS [J].

IMAMOTO, T ;

TAKIYAMA, N ;

NAKAMURA, K .

TETRAHEDRON LETTERS, 1985, 26 (39) :4763-4766

[9]

KIMBALL SD, UNPUB

[10]

KIMBALL SD, IN PRESS J MED CHEM

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