Synthesis of aristolactam analogues and evaluation of their antitumor activity

被引：57

作者：

Choi, Young Lok ^{[1
,2
]}

Kim, Joa Kyum ^{[1
]}

Choi, Sang-Un ^{[1
]}

Min, Yong-Ki ^{[1
]}

Bae, Myung-Ae ^{[1
]}

Kim, Bum Tae ^{[1
]}

Heo, Jung-Nyoung ^{[1
]}

机构：

[1] Korea Res Inst Chem Technol, Bioorgan Sci Div, Taejon 305600, South Korea

[2] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 11期

关键词：

Aristolactam; Sauristolactam; Piperolactam; Cepharanone; Anticancer; Cytotoxicity; Phenanthrene lactam; ANTIPLATELET AGGREGATION CONSTITUENTS; CYCLOADDITION APPROACH; ARISTOLOCHIC ACIDS; ALKALOIDS; APORPHINOIDS; CEPHARANONE; AMIDES; ROUTE;

D O I：

10.1016/j.bmcl.2009.04.020

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of natural aristolactams and their analogues have been prepared and evaluated for antitumor activity against human cancer cells, including multi-drug resistant cell lines. Naturally occurring aristolactams, such as aristolactam BII (cepharanone B), aristolactam BIII, aristolactam FI (piperolactam A), N-methyl piperolactam A, and sauristolactam showed moderate antitumor activities in selected cell lines. However, several synthetic aristolactam derivatives exhibited potent antitumor activities against a broad array of cancer cell lines with GI(50) values in the submicromolar range. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3036 / 3040

页数：5

共 27 条

[1] INTERMOLECULAR BENZYNE CYCLOADDITION APPROACH TO APORPHINOIDS - TOTAL SYNTHESES OF NORCEPHARADIONE-B, CEPHARADIONE-B, DEHYDROANONAINE, DUGUENAINE, DEHYDRONORNUCIFERINE, PONTEVEDRINE, O-METHYLATHEROLINE, LYSICAMINE, AND ALKALOID PO-3 [J].

ATANES, N ;

CASTEDO, L ;

GUITIAN, E ;

SAA, C ;

SAA, JM ;

SUAU, R .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2984-2988

[2] β-Phenylethylamines and the isoquinoline alkaloids [J].

Bentley, Kenneth W. .

NATURAL PRODUCT REPORTS, 2006, 23 (03) :444-463

[3] STILBENE PHOTOCYCLIZATION - SYNTHESIS OF CEPHARANONE-B [J].

CASTEDO, L ;

GUITIAN, E ;

SAA, JM ;

SUAU, R .

HETEROCYCLES, 1982, 19 (02) :279-280

[4] NEW BENZYNE APPROACH TO THE SYNTHESIS OF DEHYDROAPORPHINES, 4,5-DIOXOAPORPHINES AND ARISTOLACTAMS [J].

CASTEDO, L ;

GUITIAN, E ;

SAA, JM ;

SUAU, R .

TETRAHEDRON LETTERS, 1982, 23 (04) :457-458

[5]

Castedo L., 1990, The Alkaloids: Chemistry and Pharmacology, V39, P99, DOI DOI 10.1016/S0099-9598(08)60165-0.CHAPTER

[6] A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense [J].

Chen, YC ;

Chen, JJ ;

Chang, YL ;

Teng, CM ;

Lin, WY ;

Wu, CC ;

Chen, IS .

PLANTA MEDICA, 2004, 70 (02) :174-177

[7] Synthesis and biological evaluation of aristolactams [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Rybalko-Rosen, H ;

Léonce, S ;

Pfeiffer, B ;

Renard, P .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (24) :3557-3559

[8] Total syntheses of taliscanine, velutinam, and enterocarpam II [J].

Couture, A ;

Deniau, E ;

Grandclaudon, P ;

Hoarau, C .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :3128-3132

[9]

Couture A, 1997, SYNLETT, P1475

[10] INTRAMOLECULAR ARYNE CYCLO-ADDITION APPROACH TO ARISTOLACTAMS [J].

ESTEVEZ, JC ;

ESTEVEZ, RJ ;

GUITIAN, E ;

VILLAVERDE, MC ;

CASTEDO, L .

TETRAHEDRON LETTERS, 1989, 30 (42) :5785-5786

← 1 2 3 →