SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 13-EPI-AVERMECTINS - POTENT ANTHELMINTIC AGENTS WITH AN INCREASED MARGIN OF SAFETY

被引：27

作者：

BLIZZARD, TA

MARGIATTO, GM

MROZIK, H

SHOOP, WL

FRANKSHUN, RA

FISHER, MH

机构：

[1] Merck Sharp and Dohme Research Laboratories, Rahway, New Jersey 07065, R50G-231

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1992年 / 35卷 / 21期

关键词：

D O I：

10.1021/jm00099a014

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chemical conversion of the potent anthelmintic natural products avermectin B1 (1) and avermectin B2 (3) to the corresponding 13-epi analogs (15 and 9) is described. The novel analogs retain the full potency of the natural products but are substantially safer.

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页码：3873 / 3878

页数：6

相关论文

共 28 条

[1]

Benz G. W., 1989, Ivermectin and abamectin., P215

[2] AVERMECTIN ANALOGS WITH A SPACER BETWEEN THE AGLYCONE AND THE DISACCHARIDE [J].

BLIZZARD, T ;

MARGIATTO, G ;

LINN, B ;

MROZIK, H ;

FISHER, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1991, 1 (07) :369-372

[3] CONVERSION OF AVERMECTIN-B1 TO 19-EPI-AVERMECTIN-B1 [J].

BLIZZARD, T ;

BOSTROM, L ;

MARGIATTO, G ;

MROZIK, H ;

FISHER, M .

TETRAHEDRON LETTERS, 1991, 32 (24) :2723-2726

[4]

BLIZZARD T, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P65

[5] SYNTHESIS, REACTIVITY, AND BIOACTIVITY OF AVERMECTIN-B1-3,4-OXIDE [J].

BLIZZARD, TA ;

MROZIK, H ;

PREISER, FA ;

FISHER, MH .

TETRAHEDRON LETTERS, 1990, 31 (35) :4965-4968

[6] BRINE SHRIMP (ARTEMIA-SALINA) AS A CONVENIENT BIOASSAY FOR AVERMECTIN ANALOGS [J].

BLIZZARD, TA ;

RUBY, CL ;

MROZIK, H ;

PREISER, FA ;

FISHER, MH .

JOURNAL OF ANTIBIOTICS, 1989, 42 (08) :1304-1307

[7] AN IMPROVED PREPARATION OF THE AVERMECTIN DISACCHARIDE UNIT [J].

BLIZZARD, TA ;

MARINO, G ;

MROZIK, H ;

FISHER, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (07) :1756-1757

[8] IVERMECTIN, A NEW BROAD-SPECTRUM ANTI-PARASITIC AGENT [J].

CHABALA, JC ;

MROZIK, H ;

TOLMAN, RL ;

ESKOLA, P ;

LUSI, A ;

PETERSON, LH ;

WOODS, MF ;

FISHER, MH ;

CAMPBELL, WC ;

EGERTON, JR ;

OSTLIND, DA .

JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (10) :1134-1136

[9] THE TOTAL SYNTHESIS OF AVERMECTIN-A1A [J].

DANISHEFSKY, SJ ;

ARMISTEAD, DM ;

WINCOTT, FE ;

SELNICK, HG ;

HUNGATE, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2967-2980

[10] AVERMECTINS AND MILBEMYCINS [J].

DAVIES, HG ;

GREEN, RH .

NATURAL PRODUCT REPORTS, 1986, 3 (02) :87-121