title: Synthesis of new chromeno-annulated cis-fused pyrano[4,3-c]isoxazole derivatives via intramolecular nitrone cycloaddition and their cytotoxicity evaluation.
abstract: New cis-fused chromeno pyrano[4,3-c]isoxazole derivatives have been synthesized by intramolecular [1,3]-cycloaddition of the nitrones generated in situ from hydroxylamine derivatives and 7-O-prenyl derivatives of 8-formyl-2,3-disubstituted chromenones using PEG-400 as a reaction medium under catalyst-free conditions good to excellent yields. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis. The results showed that compounds 4b, 4c, 4d, 4e and 4k exhibit very potent antiproliferative activity against MDA-MB-231 breast cancer cells. Compounds 4a, 4c, 4e, 4i and 4k displayed potent inhibitory activity against human MCF-7 breast cancer cell lines. Compounds 4h and 4i exhibited significant anti-proliferative activity against human cervical cancer cell line, HeLa. While 4b, 4d and 4j were active against human lung cancer cell line, A549. In addition, Compound 4j was found to be the most promising against A549 (Lung cancer) with IC50 value of 0.194 μM.
authors.affiliation: Division of Organic and Biomolecular Chemistry, CSIR - Indian Institute of Chemical Technology, Hyderabad 500 067, India.
authors.forename: Naveen Kumar
authors.initials: NK
authors.lastname: Bejjanki
authors.forename: Akkaladevi
authors.initials: A
authors.lastname: Venkatesham
authors.forename: Jyothi
authors.initials: J
authors.lastname: Madda
authors.forename: Nagaiah
authors.initials: N
authors.lastname: Kommu
authors.forename: Sujitha
authors.initials: S
authors.lastname: Pombala
authors.forename: C Ganesh
authors.initials: CG
authors.lastname: Kumar
authors.forename: Kothakonda Rajendra
authors.initials: KR
authors.lastname: Prasad
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
mesh_terms: D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D007536:Isomerism; D007555:Isoxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D061986:MCF-7 Cells; D008968:Molecular Conformation; D009589:Nitrogen Oxides / Q000737:chemistry*; D011092:Polyethylene Glycols / Q000737:chemistry
chemical_list: D007555:Isoxazoles; D009589:Nitrogen Oxides; C015388:nitrones; D011092:Polyethylene Glycols