Design and synthesis of a conformationally rigid mimic of the dihydropyrimidine calcium channel modulator SQ 32,926

被引：106

作者：

Jauk, B ^{[1
]}

Pernat, T ^{[1
]}

Kappe, CO ^{[1
]}

机构：

[1] Karl Franzens Univ Graz, Inst Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

来源：

MOLECULES | 2000年 / 5卷 / 03期

关键词：

dihydropyrimidines; Biginelli reaction; isomunchnones; 1,3-dipolar cycloaddition reactions; AM1; calculations; conformation;

D O I：

10.3390/50300227

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A conformationally rigid polyheterocycle (3) which mimics the putative receptor-bound conformation of dihydropyridine-type calcium channel modulators is prepared in a seven-step reaction sequence based on a Biginelli-type cyclocondensation reaction.

引用

页码：227 / 239

页数：13

共 38 条

[1]

[Anonymous], 1999, J CHEM EDUC

[2] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .3. 3-CARBAMOYL-4-ARYL-1,2,3,4-TETRAHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS ORALLY EFFECTIVE ANTIHYPERTENSIVE AGENTS [J].

ATWAL, KS ;

SWANSON, BN ;

UNGER, SE ;

FLOYD, DM ;

MORELAND, S ;

HEDBERG, A ;

OREILLY, BC .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) :806-811

[3] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS - 2-HETEROSUBSTITUTED 4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

SCHWARTZ, J ;

MORELAND, S ;

HEDBERG, A ;

GOUGOUTAS, JZ ;

MALLEY, MF ;

FLOYD, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1510-1515

[4] DIHYDROPYRIMIDINE CALCIUM-CHANNEL BLOCKERS .2. 3-SUBSTITUTED-4-ARYL-1,4-DIHYDRO-6-METHYL-5-PYRIMIDINECARBOXYLIC ACID-ESTERS AS POTENT MIMICS OF DIHYDROPYRIDINES [J].

ATWAL, KS ;

ROVNYAK, GC ;

KIMBALL, SD ;

FLOYD, DM ;

MORELAND, S ;

SWANSON, BN ;

GOUGOUTAS, JZ ;

SCHWARTZ, J ;

SMILLIE, KM ;

MALLEY, MF .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (09) :2629-2635

[5] A revision of the Biginelli reaction under solid acid catalysis. Solvent-free synthesis of dihydropyrimidines over montmorillonite KSF [J].

Bigi, F ;

Carloni, S ;

Frullanti, B ;

Maggi, R ;

Sartori, G .

TETRAHEDRON LETTERS, 1999, 40 (17) :3465-3468

[6] DIHYDROPYRIMIDINES - NOVEL CALCIUM-ANTAGONISTS WITH POTENT AND LONG-LASTING VASODILATIVE AND ANTIHYPERTENSIVE ACTIVITY [J].

CHO, H ;

UEDA, M ;

SHIMA, K ;

MIZUNO, A ;

HAYASHIMATSU, M ;

OHNAKA, Y ;

TAKEUCHI, Y ;

HAMAGUCHI, M ;

AISAKA, K ;

HIDAKA, T ;

KAWAI, M ;

TAKEDA, M ;

ISHIHARA, T ;

FUNAHASHI, K ;

SATOH, F ;

MORITA, M ;

NOGUCHI, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2399-2406

[7] Ring conformation and ester orientation in dihydropyrimidinecarboxylates: a combined theoretical (ab initio, density functional) and X-ray crystallographic study [J].

Fabian, WMF ;

Semones, MA ;

Kappe, CO .

THEOCHEM-JOURNAL OF MOLECULAR STRUCTURE, 1998, 432 (03) :219-228

[8] Researches on pyrimidines CXXX Synthesis of 2-keto-1,2,3,4-tetrahydropyrimidines [J].

Folkers, K ;

Harwood, HJ ;

Johnson, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1932, 54 :3751-3758

[9] 1,4-DIHYDROPYRIDINES - EFFECTS OF CHIRALITY AND CONFORMATION ON THE CALCIUM-ANTAGONIST AND CALCIUM AGONIST ACTIVITIES [J].

GOLDMANN, S ;

STOLTEFUSS, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1559-1578

[10]

Goldmann S., 1991, ANGEW CHEM, V103, P1587

← 1 2 3 4 →