Synthesis and structure-activity studies of antofine analogues as potential anticancer agents

被引:93
作者
Fu, Ye
Lee, Sang Kook
Min, Hye-Young
Lee, Taeho
Lee, Jaekwang
Cheng, Maosheng
Kim, Sanghee
机构
[1] Seoul Natl Univ, Coll Pharm, Seoul 151742, South Korea
[2] Seoul Natl Univ, Coll Pharm, Inst Nat Prod Res, Seoul 110460, South Korea
[3] Ewha Womans Univ, Coll Pharm, Seoul 120750, South Korea
[4] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China
关键词
antofine; phenanthroindolizidine; structure-activity relationship; anticancer;
D O I
10.1016/j.bmcl.2006.09.080
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Due to the profound cytotoxicities and interesting biochemical aspects, phenanthroindolizidine alkaloids have received an attention as potential therapeutic leads. To define the features of the molecule that are essential for cytotoxicity, we have synthesized and evaluated a series of phenanthroindolizidine alkaloid, antofine, analogues with different substituents on the phenanthrene ring. The systematic structure activity relationship studies elucidate the essential functional group requirement of phenanthrene ring, providing the basis for further development of phenanthroindolizidine alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:97 / 100
页数:4
相关论文
共 34 条
[11]  
Gellert E., 1987, ALKALOIDS CHEM BIOL, P55
[12]   Cytotoxic alkaloids from the roots of Tylophora atrofolliculata [J].
Huang, XS ;
Gao, S ;
Fan, LH ;
Yu, SS ;
Liang, XT .
PLANTA MEDICA, 2004, 70 (05) :441-445
[13]  
Jin Z, 2004, CHINESE CHEM LETT, V15, P1164
[14]   Asymmetric total syntheses of (-)-antofine and (-)-cryptopleurine using (R)-(E)-4-(tributylstannyl)but-3-en-2-ol [J].
Kim, S ;
Lee, T ;
Lee, E ;
Lee, J ;
Fan, GJ ;
Lee, SK ;
Kim, D .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3144-3149
[15]   First asymmetric total synthesis of (-)-antofine by using an enantioselective catalytic phase transfer alkylation [J].
Kim, S ;
Lee, J ;
Lee, T ;
Park, HG ;
Kim, D .
ORGANIC LETTERS, 2003, 5 (15) :2703-2706
[16]  
Kim S, 2000, SYNTHESIS-STUTTGART, P1622
[17]   ZINC-MODIFIED CYANOBOROHYDRIDE AS A SELECTIVE REDUCING AGENT [J].
KIM, S ;
OH, CH ;
KO, JS ;
AHN, KH ;
KIM, YJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (11) :1927-1932
[18]   Total syntheses of (±)-cryptopleurine, (±)-antofine and (±)-deoxypergularinine [J].
Lebrun, S ;
Couture, A ;
Deniau, E ;
Grandclaudon, P .
TETRAHEDRON, 1999, 55 (09) :2659-2670
[19]   Synthesis and evaluation of cytotoxicity of stilbene analogues [J].
Lee, SK ;
Nam, KA ;
Hoe, YH ;
Min, HY ;
Kim, EY ;
Ko, H ;
Song, S ;
Lee, T ;
Kim, S .
ARCHIVES OF PHARMACAL RESEARCH, 2003, 26 (04) :253-257
[20]   Cytotoxic activity and G2/M cell cycle arrest mediated by antofine, a phenanthroindolizidine alkaloid isolated from Cynanchum paniculatum [J].
Lee, SK ;
Nam, KA ;
Heo, YH .
PLANTA MEDICA, 2003, 69 (01) :21-25