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

Bioorg Med Chem Lett. 2014 Mar 1;24(5):1349-51. doi: 10.1016/j.bmcl.2014.01.038.

P Sambasiva Rao ¹, C Kurumurthy ¹, B Veeraswamy ¹, Y Poornachandra ², C Ganesh Kumar ², B Narsaiah ³

Affiliations

1 Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
2 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India.
3 Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India. Electronic address: narsaiah@iict.res.in.

PMID: 24507927 DOI: 10.1016/j.bmcl.2014.01.038

Abstract

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 <12 μM.

Keywords

Aldoxime; Cytotoxic activity; Isoxazole; Jones reagent; Quinoline.

Name
Email *

	Sorry, but the email address you supplied was invalid.