title: Design, microwave-mediated synthesis and biological evaluation of novel 4-aryl(alkyl)amino-3-nitroquinoline and 2,4-diaryl(dialkyl)amino-3-nitroquinolines as anticancer agents.
abstract: Design, microwave-assisted synthesis of novel 4-aryl (alkyl)amino-3-nitroquinoline (1a-1l) and 2,4-diaryl (dialkyl)amino-3-nitroquinolines (2a-2k and 3a) via regioselective and complete nucleophilic substitution of 2,4-dichloro-3-nitroquinoline, respectively in water are presented. The newly synthesized compounds were evaluated for the first time for antiproliferative activity against EGFR overexpressing human lung (A-549 and H-460) and colon (HCT-116-wild type and HCT-116-p53 null) cancer cell lines. Some notions about structure-activity relationships (SAR) are presented. Compounds 2e, 2f, 2j and 3a overall exhibited excellent anticancer activity comparable to erlotinib which was used as a positive control. Molecular modeling studies disclosed the recognition pattern of the compounds and also supported the observed SAR.
authors.affiliation: Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India.
authors.forename: Monika
authors.initials: M
authors.lastname: Chauhan
authors.affiliation: Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India.
authors.forename: Anil
authors.initials: A
authors.lastname: Rana
authors.affiliation: Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India.
authors.forename: Jimi Marin
authors.initials: JM
authors.lastname: Alex
authors.affiliation: Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India.
authors.forename: Arvind
authors.initials: A
authors.lastname: Negi
authors.affiliation: Centre for Genetic Diseases and Molecular Medicine, Central University of Punjab, Bathinda 151 001, India.
authors.forename: Sandeep
authors.initials: S
authors.lastname: Singh
authors.affiliation: Laboratory for Drug Design and Synthesis, Centre for Chemical and Pharmaceutical Sciences, School of Basic and Applied Sciences, Central University of Punjab, Bathinda 151 001, India. Electronic address: raj.khunger@gmail.com.
authors.forename: Raj
authors.initials: R
authors.lastname: Kumar
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008872:Microwaves; D008958:Models, Molecular; D009600:Nitroquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013057:Spectrum Analysis / Q000379:methods; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D009600:Nitroquinolines
keywords: 2,4-Diaminoquinolines; Anticancer activity; Microwave heating; Molecular modeling; Synthesis