1. Synthesis and biological activities of novel pyrazolomatrine derivatives
- Author
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Wenlong Kong, Yinhe Bao, Hui Xu, and Qianjun Ma
- Subjects
Steric effects ,Sophora ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Crystallography, X-Ray ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,Alkaloids ,Matrine ,Drug Discovery ,Animals ,Matrines ,Molecular Biology ,Acaricides ,Natural product ,Quinolizidine ,biology ,Molecular Structure ,010405 organic chemistry ,Alkaloid ,Organic Chemistry ,biology.organism_classification ,0104 chemical sciences ,Tetranychus cinnabarinus ,010404 medicinal & biomolecular chemistry ,chemistry ,Aphids ,Proton NMR ,Molecular Medicine ,Pyrazoles ,Female ,Tetranychidae ,Quinolizines - 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.
- Published
- 2018