Synthesis and biological activities of novel pyrazolomatrine derivatives

Bioorg Med Chem Lett. 2018 Nov 1;28(20):3338-3341. doi: 10.1016/j.bmcl.2018.09.008. Epub 2018 Sep 6.

Abstract

In continuation of our program aimed at the development of new natural product-based pesticides, a series of novel pyrazolomatrine derivatives were prepared by structural modifications of matrine, isolated as a quinolizidine alkaloid from the roots of Sophora flave. Their structures were confirmed by 1H NMR, HRMS, etc. Moreover, the steric structures of three compounds were determined by single-crystal X-ray diffraction. Among all derivatives, 19-(naphthyl-2-oyl)pyrazolomatrine (5y) showed 3.13-fold more potent acaricidal activity than its precusor matrine against Tetranychus cinnabarinus; 19-(4-methylbenzoyl)pyrazolomatrine (5j) and 19-(3,5-dimethylbenzoyl)pyrazolomatrine (5k) displayed the promising aphicidal activity against Aphis citricola van der. Their structure-activity relationships were also observed.

Keywords: Acaricidal activity; Aphicidal activity; Matrine; Natural-product-based; Pyrazolomatrine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acaricides / chemical synthesis
  • Acaricides / chemistry
  • Acaricides / toxicity*
  • Alkaloids / chemical synthesis
  • Alkaloids / chemistry
  • Alkaloids / toxicity*
  • Animals
  • Aphids / drug effects
  • Crystallography, X-Ray
  • Female
  • Matrines
  • Molecular Structure
  • Pyrazoles / chemical synthesis
  • Pyrazoles / chemistry
  • Pyrazoles / toxicity*
  • Quinolizines / chemical synthesis
  • Quinolizines / chemistry
  • Quinolizines / toxicity*
  • Structure-Activity Relationship
  • Tetranychidae / drug effects

Substances

  • Acaricides
  • Alkaloids
  • Pyrazoles
  • Quinolizines
  • Matrines