Chemical modification of nodulisporic acid A: Preliminary structure-activity relationships

被引:20
作者
Meinke, PT
Ayer, MB
Colletti, SL
Li, CS
Lim, J
Ok, D
Salva, S
Schmatz, DM
Shih, TL
Shoop, WL
Warmke, LM
Wyvratt, MJ
Zakson-Aiken, M
Fisher, MH
机构
[1] Merck Res Labs, Dept Med Chem, Rahway, NJ 07065 USA
[2] Merck Res Labs, Dept Basic Anim Sci Res, Rahway, NJ 07065 USA
关键词
D O I
10.1016/S0960-894X(00)00469-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Medicinal chemistry efforts were initiated to identify the key constituents of the nodulisporic acid A (1) pharmacophore that are integral to its potent insecticidal activity. New semisynthetic derivatives delineated 1 into 'permissive' and 'nonpermissive' regions and led to the discovery of new nodulisporamides with significantly improved flea efficacy. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2371 / 2374
页数:4
相关论文
共 22 条
[1]   Ion channels as targets for insecticides [J].
Bloomquist, JR .
ANNUAL REVIEW OF ENTOMOLOGY, 1996, 41 :163-190
[2]  
BRUCE CI, 1999, ANN M AM ASS VET PAR
[3]  
CASTRO B, 1975, TETRAHEDRON LETT, V14, P1219
[4]   ESTERIFICATION OF CARBOXYLIC-ACIDS USING BOP OR PYBOP [J].
COSTE, J ;
CAMPAGNE, JM .
TETRAHEDRON LETTERS, 1995, 36 (24) :4253-4256
[5]   AVERMECTINS AND MILBEMYCINS [J].
DAVIES, HG ;
GREEN, RH .
NATURAL PRODUCT REPORTS, 1986, 3 (02) :87-121
[6]  
DRYDEN MW, 1999, ANN M AM ASS VET PAR
[7]  
Fisher M.H., 1984, MACROLIDE ANTIBIOTIC, P553
[8]  
Fisher MH, 1997, ACS SYM SER, V658, P220
[9]   FACILE REDUCTION OF ETHYL THIOL ESTERS TO ALDEHYDES - APPLICATION TO A TOTAL SYNTHESIS OF (+)-NEOTHRAMYCIN-A METHYL-ETHER [J].
FUKUYAMA, T ;
LIN, SC ;
LI, LP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (19) :7050-7051
[10]   Isolation and structure of nodulisporic acid A1 and A2, novel insecticides from a Nodulisporium sp. [J].
Hensens, OD ;
Ondeyka, JG ;
Dombrowski, AW ;
Ostlind, DA ;
Zink, DL .
TETRAHEDRON LETTERS, 1999, 40 (30) :5455-5458