First synthesis and pharmacological evaluation of benzoindolizidine and benzoquinolizidine analogues of α- and β-peltatin

被引：17

作者：

Couture, A ^{[1
]}

Deniau, E

Grandclaudon, P

Lebrun, S

Léonce, S

Renard, P

Pfeiffer, B

机构：

[1] Univ Sci & Technol Lille, CNRS, ESA 8009, Chim Organ Phys Lab, F-59655 Villeneuve Dascq, France

[2] Inst Rech Int Servier, Div Cancerol Expt, F-92415 Suresnes, France

[3] ADIR, F-92415 Courbevoie, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2000年 / 8卷 / 08期

关键词：

D O I：

10.1016/S0968-0896(00)00130-9

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：

The benzoindolizidine and-quinolizidine analogues of alpha- and beta-peltatin were designed and synthesized by two different synthetic routes involving as the key step the Bischler-Napieralski cyclization of suitably substituted N-acyl-2-arylmethylpyrrolidine and -piperidine derivatives. The in vitro biological activity of these analogues as well as some of their derivatives was subsequently evaluated. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2113 / 2125

页数：13

共 44 条

[1]

[Anonymous], 1980, ANTICANCER AGENTS BA

[2]

ARAI Y, 1968, Yakugaku Zasshi, V88, P1197

[3]

AYRES DC, 1990, LIGNANS CHEM BIOL CL

[4] THE SYNTHESIS OF 2-AZAPODOPHYLLOTOXINS [J].

BOSMANS, JP ;

VANDEREYCKEN, J ;

VANDEWALLE, M ;

HULKENBERG, A ;

VANHES, R ;

VEERMAN, W .

TETRAHEDRON LETTERS, 1989, 30 (29) :3877-3880

[5]

BRADLEY R, 1928, J CHEM SCO, P1555

[6] TOTAL SYNTHESIS OF (+/-)ISO BETA-PELTATIN AND ITS ANALOGS [J].

BROWN, E ;

LORIOT, M ;

ROBIN, JP .

TETRAHEDRON LETTERS, 1982, 23 (09) :949-952

[7] A 6-STEP SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].

COMINS, DL ;

HONG, H ;

SAHA, JK ;

GAO, JH .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5120-5121

[8]

CORTESE F, 1977, J BIOL CHEM, V252, P1134

[9] A new synthetic route to 2-alkyl-4-aryl-1(2H)-isoquinolones and 2-alkyl-4-aryl-1,2,3,4-tetrahydroisoquinolines [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Woisel, P .

TETRAHEDRON, 1996, 52 (12) :4433-4448

[10]

EMMENEGGER H, 1961, ARZNEIMITTEL-FORSCH, V327, P459

← 1 2 3 4 5 →