MULTISTEP SYNTHESIS AND NEMATICIDAL ACTIVITY OF 2-(8-AZABICYCLO[3.2.1]OCTAN-3-YL)-3-IMINO-2,3-DIHYDRO-1<i>H</i>-ISOINDOL-1-ONE DERIVATIVES

Authors

  • Jun Xu School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
  • Tianjiao Yang School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
  • Jiayi Wang School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China
  • Gonghua Song School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China

DOI:

https://doi.org/10.1007/5882

Keywords:

azabicyclo, iminoisoindoline, isocyanide insertion, nematicidal activity.

Abstract

Novel 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-ones derived from 5-HT3 receptor antagonists hexahydroazepinylbenzamides were designed and synthesized through isocyanide insertion reaction. All target compounds were evaluated against
pinewood nematodes B. xylophilus and root-knot nematodes M. incognita. Good lethal rate (75%) for 3-(tert-butylimino)-5-chloro-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one and serious nervous curl effect against pinewood nematodes B. xylophilus for 3-(tert-butylimino)-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one were observed at 10 mg/l. The inhibition activities of 3-[(4-methoxyphenyl)imino]-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one against root-knot nematodes M. incognita were 84% at 160 mg/l and 60% at 20 mg/l for in vitro test and test tube test, respectively.

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Published

2021-01-26

Issue

Vol. 57 No. 1 (2021)

Section

Original Papers