Insecticidal heterolignans-Tubuline polymerization inhibitors with activity against chewing pests

被引：40

作者：

Frackenpohl, Jens ^{[1
]}

Adelt, Isabelle ^{[2
]}

Antonicek, Horst ^{[2
]}

Arnold, Christian ^{[2
]}

Behrmann, Patricia ^{[2
]}

Blaha, Nicole ^{[1
]}

Boehmer, Jutta ^{[2
]}

Gutbrod, Oliver ^{[2
]}

Hanke, Roman ^{[2
]}

Hohmann, Sabine ^{[1
]}

van Houtdreve, Marc ^{[2
]}

Loesel, Peter ^{[2
]}

Malsam, Olga ^{[2
]}

Melchers, Martin ^{[2
]}

Neufert, Valentina ^{[2
]}

Peschel, Elisabeth ^{[1
]}

Reckmann, Udo ^{[2
]}

Schenke, Thomas ^{[2
]}

Thiesen, Hans-Peter ^{[2
]}

Velten, Robert ^{[2
]}

Vogelsang, Kathrin ^{[2
]}

Weiss, Hans-Christoph ^{[3
]}

机构：

[1] Bayer CropSci AG, D-65926 Frankfurt, Germany

[2] Bayer CropSci AG, D-40789 Monheim, Germany

[3] Currenta GmbH, D-51368 Leverkusen, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 12期

关键词：

Heterolignan; Dihydropyridine; Tubuline polymerization inhibitor; Insecticide; JUNIPERUS-SABINA; DERIVATIVES; PODOPHYLLOTOXIN; APOPTOSIS; LIGNANS; AGENTS;

D O I：

10.1016/j.bmc.2009.01.042

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Starting from natural product podophyllotoxin 1 substituted heterolignans were identified with promising insecticidal in vivo activity. The impact of substitution in each segment of the core structure was investigated in a detailed SAR study, and variation of substituents in both aromatic moieties afforded derivatives 5 and 43 with broad insecticidal activity against lepidopteran and coleopteran species. In vitro measurements supported by modeling studies indicate that heterolignans 3-134 act as tubuline polymerization inhibitors interacting with the colchicine-binding site. Insect specific structure-activity effects were observed showing that the insecticidal SAR described herein differs from reported cytotoxicity studies. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4160 / 4184

页数：25

共 22 条

[1]

Desbene Stephanie, 2002, Current Medicinal Chemistry - Anti-Cancer Agents, V2, P71, DOI 10.2174/1568011023354353

[2] Synthesis and insecticidal activities of pyridine ring derivatives of podophyllotoxin [J].