The synthesis and biological activity of two analogs of the anti-HIV alkaloid michellamine B

被引：35

作者：

Upender, V ^{[1
]}

Pollart, DJ ^{[1
]}

Liu, J ^{[1
]}

Hobbs, PD ^{[1
]}

Olsen, C ^{[1
]}

Chao, WR ^{[1
]}

Bowden, B ^{[1
]}

Crase, JL ^{[1
]}

Thomas, DW ^{[1
]}

Pandey, A ^{[1
]}

Lawson, JA ^{[1
]}

Dawson, MI ^{[1
]}

机构：

[1] SO RES INST,VIRUCIDAL TESTING SECT,BIRMINGHAM,AL 35205

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 04期

关键词：

D O I：

10.1002/jhet.5570330460

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two simplified analogs of the dimeric naphthalenyltetrahydroisoquinoline alkaloid michellamine B [4',4 ''-didesmethoxy-2',2 ''-didesmethylmichellamine B and 6,8-dihydroxy-5-(1',1 ''-dihydroxy-2',2 ''-binaphthalen-4'-yl)-1R, 3R-dimethyl-1,2,3,4-tetrahydroisoquinoline] were synthesized using Suzuki palladium-catalyzed biaryl cross-coupling of 4-(2-benzyl-6,8-dibenzyloxy-1R,3R-dimethyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-1-benzyloxy-2-bromonaphthalene to its corresponding atropisomeric 2-naphthaleneboronic acid and 1-benzyloxy-2-naphthaleneboronic acid, respectively. These analogs inhibited recombinant HIV reverse transcriptase with IC50 values of 62 mu M and 1000 mu M, respectively, whereas the IC50 value for michellamine B was 33 mu M. Both michellamine B and the analogs inhibited the phosphorylation of histones by rat brain protein kinase C. The analogs were more active (IC50 values of 36 mu M and 30 mu M, respectively) than michellamine B (IC50 = 130 mu M).

引用

页码：1371 / 1384

页数：14

共 26 条

[1] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].

BOYD, MR ;

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

MCMAHON, JB ;

BUCKHEIT, RW ;

BRINGMANN, G ;

SCHAFFER, M ;

CRAGG, GM ;

THOMAS, DW ;

JATO, JG ;

CARDELLINA, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745

[2]

BOYD MR, 1991, Patent No. 7684197

[3] ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C [J].

BRINGMANN, G ;

HARMSEN, S ;

HOLENZ, J ;

GEUDER, T ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

TETRAHEDRON, 1994, 50 (32) :9643-9648

[4] ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B [J].

BRINGMANN, G ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HENSCHEL, P ;

SCHAFFER, M ;

STABLEIN, M ;

KELLY, TR ;

BOYD, MR .

HETEROCYCLES, 1994, 39 (02) :503-508

[5] ACETOGENIC ISOQUINOLINE ALKALOIDS .11. REGIOSELECTIVE AND ATROPOISOMERIC-SELECTIVE ARYL COUPLING TO GIVE NAPHTHYL ISOQUINOLINE ALKALOIDS - THE 1ST TOTAL SYNTHESIS OF (-)-ANCISTROCLADINE [J].

BRINGMANN, G ;

JANSEN, JR ;

RINK, HP .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (10) :913-915

[6]

BRINGMANN G, 1993, ANGEW CHEM INT EDIT, V32, P1990

[7]

DAHMER A, 1904, LIEBIGS ANN CHEM, V333, P346

[8]

DERMER VH, 1939, J ORG CHEM, V3, P289

[9] REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].

ELAMIN, B ;

ANANTHARAMAIAH, GM ;

ROYER, GP ;

MEANS, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444

[10]

GREY RW, 1980, HELV CHIM ACTA, V63, P315

← 1 2 3 →