title: In situ Bronsted-Lowry acid catalyzed syntheses, characterization, single crystal XRD, electronic spectral-, DPPH radical scavenging-, and DNA protection studies of aryl-3,3'-bis(indolyl)methanes.
abstract: A series of novel aryl-3,3'-bis(indolyl)methanes (BIMs) were synthesized using indole and formylphenoxyaliphatic acid(s) in water in the absence of any catalyst. The formylphenoxyaliphatic acid behaves as an in situ Bronsted-Lowry acid catalyst in water. UV-Visible and fluorescence spectra of the compounds were recorded in selected solvents. The gas phase geometry optimization of the compounds were achieved using DFT calculations at B3LYP/3-21G((*)) level of theory. The electronic properties, such as HOMO-LUMO energies were calculated using the above method based on the optimized structure. Compounds have better DPPH radical scavenging activity and reduction of oxidative damage of DNA.
authors.affiliation: Faculty of Chemistry, Department of Science and Humanities, Dr. Mahalingam College of Engineering and Technology (Dr. MCET), Udumalai Road, Pollachi 642 003, Tamilnadu, India.
authors.forename: G S
authors.initials: GS
authors.lastname: Suresh Kumar
authors.affiliation: Department of Chemistry, Manonmaniam Sundaranar University, Tirunelveli 627 012, Tamilnadu, India.
authors.forename: A
authors.initials: A
authors.lastname: Antony Muthu Prabhu
authors.affiliation: Department of Chemistry, APC Mahalakshmi College for Women, Toothukkudi 628 002, Tamilnadu, India.
authors.forename: P G
authors.initials: PG
authors.lastname: Seethalaksmi
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, TX 77842, USA.
authors.forename: N
authors.initials: N
authors.lastname: Bhuvanesh
authors.affiliation: Department of Chemistry, Noorul Islam University, Kumaracoil, Thuckalay 629 180, Tamilnadu, India. Electronic address: skumarmsu@yahoo.com.
authors.forename: S
authors.initials: S
authors.lastname: Kumaresan
mesh_terms: D000818:Animals; D001713:Biphenyl Compounds / Q000378:metabolism; D002417:Cattle; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008958:Models, Molecular; D010851:Picrates / Q000378:metabolism
chemical_list: C512018:1,1-bis(3'-indolyl)methane; D001713:Biphenyl Compounds; D016166:Free Radical Scavengers; D007211:Indoles; D010851:Picrates; D004247:DNA; C427203:calf thymus DNA; C004931:1,1-diphenyl-2-picrylhydrazyl
keywords: 3,3′-Bis(indolyl)methanes; Crystal structure; DNA protection; DPPH radical scavenging; Density functional theory