Synthesis of novel 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives and their cytotoxic activity

The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having α-hy...

Full description

Saved in:
Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-03, Vol.24 (5), p.1349-1351
Main Authors: Sambasiva Rao, P, Kurumurthy, C, Veeraswamy, B, Poornachandra, Y, Ganesh Kumar, C, Narsaiah, B
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - toxicity
Cell Line, Tumor
Cell Survival - drug effects
Drug Screening Assays, Antitumor
Humans
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Isoxazoles - toxicity
Quinolines - chemistry
Schiff Bases - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The propargyl alcohol on reaction with aldoxime and NaOCl in DCM gave exclusively (3-arylisoxazol-5-yl) methanol 1. The compound 1 was oxidized to an aldehyde 2 followed by reaction with aniline resulted in Schiff's base 3. The compounds 3 were further reacted with various aldehydes having α-hydrogen using molecular iodine as catalyst and which yielded 5-(3-alkylquinolin-2-yl)-3-aryl isoxazole derivatives 4. All the final compounds 4 were screened against four human cancer cell lines (A549, COLO 205, MDA-MB 231 and PC-3) and among these compounds 4n showed potent cytotoxicity against all the cell lines at IC50 values of
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2014.01.038