Synthesis and cytotoxicity of novel isomeric C-seco limonoids

Attempts to cleave the C-ring in the bioactive limonoids characteristic of the species Azadirachta indica A. Juss using BF 3·OEt 2 and (C 4H 9) 4NBr resulted in novel isomeric C-seco limonoids. Structure related cytotoxic properties of the isomers and the native compounds have been studied using bri...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2006-08, Vol.41 (8), p.997-1002
Main Authors: Genupur, Anitha, Jesu, Josepha Lourdu Raj, Srinivasan, Narasimhan, Kamalakaran, Anand Solomon, Sundar, Rajan Sundararajan
Format: Article
Language:English
Subjects:
Animals
Biological and medical sciences
C-seco limonoids
Cell Line, Tumor
Crustacea
Cytotoxicity
Drug Screening Assays, Antitumor
Humans
Isomerisation
Limonins - chemical synthesis
Limonins - chemistry
Limonins - pharmacology
Magnetic Resonance Spectroscopy
Medical sciences
Miscellaneous
Pharmacology. Drug treatments
Structure activity relationship
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Summary:Attempts to cleave the C-ring in the bioactive limonoids characteristic of the species Azadirachta indica A. Juss using BF 3·OEt 2 and (C 4H 9) 4NBr resulted in novel isomeric C-seco limonoids. Structure related cytotoxic properties of the isomers and the native compounds have been studied using brine shrimp lethality bioassay (BSLB) method and molecular descriptors viz., theoretical and chromatographic hydrophobicity constants, oxidation state and molecular modelling studies. The O–O diad distances reveal the significance of the orientation of the furan ring in enhancing the cytotoxicity of the molecule.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2006.04.003