Synthesis and anticancer activity of side chain analogs of the crambescidin alkaloids

被引:28
作者
Aron, ZD
Pietraszkiewicz, H
Overman, LE
Valeriote, F
Cuevas, C
机构
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
[2] Josephine Ford Canc Ctr, Detroit, MI 48202 USA
[3] Pharma Mar SA, Madrid 28770, Spain
关键词
D O I
10.1016/j.bmcl.2004.04.071
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Twenty three side chain analogs of the crambescidin alkaloids were prepared from the corresponding pentacyclic zwitterionic core acid. In the crambescidin 800 and 657 series, potency increased with increasing chain length. In addition, substantial variations in tumor selectivity with structure were seen. Crambescidin analogs having short, nonpolar side chains were identified for the first time as promising anticancer agents. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3445 / 3449
页数:5
相关论文
共 26 条
[1]   The tethered Biginelli condensation in natural product synthesis [J].
Aron, ZD ;
Overman, LE .
CHEMICAL COMMUNICATIONS, 2004, (03) :253-265
[2]   POLYCYCLIC GUANIDINE ALKALOIDS FROM THE MARINE SPONGE CRAMBE-CRAMBE AND CA++ CHANNEL BLOCKER ACTIVITY OF CRAMBESCIDIN-816 [J].
BERLINCK, RGS ;
BRAEKMAN, JC ;
DALOZE, D ;
BRUNO, I ;
RICCIO, R ;
FERRI, S ;
SPAMPINATO, S ;
SPERONI, E .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07) :1007-1015
[3]   Natural guanidine derivatives [J].
Berlinck, RGS .
NATURAL PRODUCT REPORTS, 2002, 19 (05) :617-649
[4]   Synthesis and biological activity of analogues of ptilomycalin A [J].
Black, GP ;
Coles, SJ ;
Hizi, A ;
Howard-Jones, AG ;
Hursthouse, MB ;
McGown, AT ;
Loya, S ;
Moore, CG ;
Murphy, PJ ;
Smith, NK ;
Walshe, NDA .
TETRAHEDRON LETTERS, 2001, 42 (19) :3377-3381
[5]   Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora [J].
Braekman, JC ;
Daloze, D ;
Tavares, R ;
Hajdu, E ;
Van Soest, RWM .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (02) :193-196
[6]   Crambescidin 826 and dehydrocrambine A:: New polycyclic guanidine alkaloids from the marine sponge Monanchora sp that inhibit HIV-1 fusion [J].
Chang, LC ;
Whittaker, NF ;
Bewley, CA .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (11) :1490-1494
[7]   A practical entry to the crambescidin family of guanidine alkaloids. Enantioselective total syntheses of ptilomycalin A, crambescidin 657 and its methyl ester (neofolitispates 2), and crambescidin 800 [J].
Coffey, DS ;
McDonald, AI ;
Overman, LE ;
Rabinowitz, MH ;
Renhowe, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4893-4903
[8]   Enantioselective total syntheses of 13,14,15-isocrambescidin 800 and 13,14,15-isocrambescidin 657 [J].
Coffey, DS ;
Overman, LE ;
Stappenbeck, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4904-4914
[9]   Marine natural products [J].
Faulkner, DJ .
NATURAL PRODUCT REPORTS, 2002, 19 (01) :1-48
[10]  
Georgieva A, 2003, SYNTHESIS-STUTTGART, P1427