191283-15-5Relevant academic research and scientific papers
Bioactive isoxazoline and grime derivatives from 7-ketolignans
Miguel del Corral, Jose M.,Gordaliza, Marina,Castro, M. Angeles,Lopez-Vazquez, M. Luisa,Garcia-Gravalos, M. Dolores,Broughton, Howard B.,San Feliciano, Arturo
, p. 6555 - 6564 (1997)
A new type of cyclolignans with an isoxazoline ring fused to the cyclolignan core has been prepared from 7-ketolignanolides by reaction with hydroxylamine. The corresponding 7-oxime derivatives have also been obtained. The compounds prepared have been evaluated for their cytotoxic activities over four cell lines.
Synthesis and insecticidal activity of novel hydrazone compounds derived from a naturally occurring lignan podophyllotoxin against Mythimna separata (Walker)
Wang, Yi,Yu, Xiang,Zhi, Xiaoyan,Xiao, Xiao,Yang, Chun,Xu, Hui
, p. 2621 - 2624 (2014/06/09)
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, a series of novel hydrazone derivatives of podophyllotoxin, which is a naturally occurring aryltetralin lignan and isolated as the main secondary metabolite from the roots and rhizomes of Podophyllum species, were synthesized and evaluated as insecticidal agents against the pre-third-instar larvae of oriental armyworm, Mythimna separata (Walker) in vivo at 1 mg/mL. Especially compounds 8i, 8j, 8t, and 8u showed the more potent insecticidal activity with the final mortality rates greater than 60%.
Synthesis and quantitative structure-activity relationship (QSAR) study of novel isoxazoline and oxime derivatives of podophyllotoxin as insecticidal agents
Wang, Yi,Shao, Yonghua,Wang, Yangyang,Fan, Lingling,Yu, Xiang,Zhi, Xiaoyan,Yang, Chun,Qu, Huan,Yao, Xiaojun,Xu, Hui
, p. 8435 - 8443 (2012/10/29)
In continuation of our program aimed at the discovery and development of natural-product-based insecticidal agents, 33 isoxazoline and oxime derivatives of podophyllotoxin modified in the C and D rings were synthesized and their structures were characterized by Proton nuclear magnetic resonance ( 1H NMR), high-resolution mass spectrometry (HRMS), electrospray ionization-mass spectrometry (ESI-MS), optical rotation, melting point (mp), and infrared (IR) spectroscopy. The stereochemical configurations of compounds 5e, 5f, and 9f were unambiguously determined by X-ray crystallography. Their insecticidal activity was evaluated against the pre-third-instar larvae of northern armyworm, Mythimna separata (Walker), in vivo. Compounds 5e, 9c, 11g, and 11h especially exhibited more promising insecticidal activity than toosendanin, a commercial botanical insecticide extracted from Melia azedarach. A genetic algorithm combined with multiple linear regression (GA-MLR) calculation is performed by the MOBY DIGS package. Five selected descriptors are as follows: one two-dimensional (2D) autocorrelation descriptor (GATS4e), one edge adjacency indice (EEig06x), one RDF descriptor (RDF080v), one three-dimensional (3D) MoRSE descriptor (Mor09v), and one atom-centered fragment (H-052) descriptor. Quantitative structure-activity relationship studies demonstrated that the insecticidal activity of these compounds was mainly influenced by many factors, such as electronic distribution, steric factors, etc. For this model, the standard deviation error in prediction (SDEP) is 0.0592, the correlation coefficient (R2) is 0.861, and the leave-one-out cross-validation correlation coefficient (Q2 loo) is 0.797.
13C NMR data for 7- and/or 9-aza-substituted naphthalenecyclolignans
Castro, Ma. Angeles,Del Corral, Jose Ma. Miguel,Lopez-Vazquez, Ma. Luisa,Garcia, Pablo A.,San Feliciano, Arturo,Gordaliza, Marina
, p. 808 - 815 (2007/10/03)
13C NMR assignments are provided for 45 7- and/or 9-aza-substituted naphthalenecyclolignans.
