title: Gold catalyzed double condensation reaction: Synthesis, antimicrobial and cytotoxicity of spirooxindole derivatives.
abstract: Microwave assisted synthesis of spirooxindoles via tandem double condensation between isatins and 4-hydroxycoumarin under gold catalysis is reported. The reaction is practical to perform, since the products can be isolated by simple filtration without requiring tedious column chromatography. The scope of this chemistry is exemplified by preparing structurally diverse spirooxindoles (22 examples) in excellent yields. Antimicrobial evaluation of the synthesized compounds revealed that three compounds (3a, 3f and 3s) exhibited significant MIC values in comparison to the standard drugs. Molecular docking studies of these compounds with AmpC-β-lactamase receptor revealed that 3a exhibited minimum binding energy (-117.819kcal/mol) indicating its strong affinity towards amino acid residues via strong hydrogen bond interaction. All compounds were also evaluated for their in vitro cytotoxicity against COLO320 cancer cells. Biological assay and molecular docking studies demonstrated that 3g is the most active compound in terms of its low IC50 value (50.0μM) and least free energy of binding (-8.99kcal/mol) towards CHK1 receptor, respectively.
authors.affiliation: Department of Chemistry, Siddha Central Research Institute, Central Council for Research in Siddha, Arumbakkam, Chennai 600106, Tamil Nadu, India.
authors.forename: K
authors.initials: K
authors.lastname: Parthasarathy
authors.affiliation: Functional Materials Division, CSIR-Central Electrochemical Research Institute, Karaikudi 630003, Tamil Nadu, India. Electronic address: chandrasekar.praveen@gmail.com.
authors.forename: Chandrasekar
authors.initials: C
authors.lastname: Praveen
authors.affiliation: Department of Chemistry, Ramakrishna Mission Vivekananda College, Mylapore, Chennai 600004, Tamil Nadu, India.
authors.forename: J C
authors.initials: JC
authors.lastname: Jeyaveeran
authors.affiliation: Department of Chemistry, Ramakrishna Mission Vivekananda College, Mylapore, Chennai 600004, Tamil Nadu, India.
authors.forename: A A M
authors.initials: AA
authors.lastname: Prince
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D001665:Binding Sites; D002384:Catalysis; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D000071877:Checkpoint Kinase 1 / Q000737:chemistry; D003110:Colonic Neoplasms / Q000188:drug therapy; D003374:Coumarins / Q000737:chemistry; D006046:Gold / Q000737:chemistry*; D006801:Humans; D006860:Hydrogen Bonding; D007211:Indoles / Q000737:chemistry* / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D008826:Microbial Sensitivity Tests; D008872:Microwaves; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000890:Anti-Infective Agents; D003374:Coumarins; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole; D006046:Gold; C030123:coumarin; C000605867:CHEK1 protein, human; D000071877:Checkpoint Kinase 1
keywords: Biological activity; Gold catalysis; Microwave chemistry; Molecular docking; Spirooxindoles