title: Cu(OTf)2 catalyzed three component reaction: efficient synthesis of spiro[indoline-3,4'-pyrano[3,2-b]pyran derivatives and their anticancer potency towards A549 human lung cancer cell lines.
abstract: Cu(OTf)2 catalyzed efficient synthesis of spiropyrano[3,2-b]pyran-4(8H)-ones is accomplished via one-pot three component reaction between isatin, kojic acid and active methylenes. This synthetic protocol is operationally simple and affords product with good to excellent yields at a short reaction time. The synthesized compounds were evaluated for their tumor cell growth inhibitory activity against the human lung cancer cell line (A549) and found that 13 compounds exhibited moderate to good anticancer potency. Molecular docking studies were performed for all the synthesized compounds and the results showed that compound 4e showed greater affinity for anaplastic lymphoma kinase (ALK) receptor.
authors.affiliation: Organic Chemistry Division, Central Leather Research Institute (CSIR), Adyar, Chennai 600 020, India.
authors.forename: K
authors.initials: K
authors.lastname: Parthasarathy
authors.forename: C
authors.initials: C
authors.lastname: Praveen
authors.forename: C
authors.initials: C
authors.lastname: Balachandran
authors.forename: P
authors.initials: P
authors.lastname: Senthil kumar
authors.forename: S
authors.initials: S
authors.lastname: Ignacimuthu
authors.forename: P T
authors.initials: PT
authors.lastname: Perumal
mesh_terms: D000077548:Anaplastic Lymphoma Kinase; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D001665:Binding Sites; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D006801:Humans; D007510:Isatin / Q000737:chemistry; D008175:Lung Neoplasms / Q000378:metabolism / Q000473:pathology; D008698:Mesylates / Q000737:chemistry*; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D017434:Protein Structure, Tertiary; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D011753:Pyrones / Q000737:chemistry; D020794:Receptor Protein-Tyrosine Kinases / Q000737:chemistry / Q000378:metabolism; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D008698:Mesylates; D011714:Pyrans; D011753:Pyrones; D013141:Spiro Compounds; C011890:kojic acid; D007510:Isatin; C000626173:ALK protein, human; D000077548:Anaplastic Lymphoma Kinase; D020794:Receptor Protein-Tyrosine Kinases; C012077:trifluoromethanesulfonic acid