title: Synthesis, antidepressant and antifungal evaluation of novel 2-chloro-8-methylquinoline amine derivatives.
abstract: A new series of N-[(2-chloro-8-methylquinolin-3-yl)methyl]-(substituted)-aniline/butylamine/cyclohexylamine/benzylamine derivatives (4a-p) was synthesized by nucleophilic substitution reaction of 2-chloro-3-(chloromethyl)-8-methylquinoline 3 with various aliphatic and aromatic amines in absolute ethanol in the presence of triethylamine (TEA). The newly synthesized secondary amines were characterized by the combined use of IR, 1H NMR, 13C NMR, mass spectral data and microanalyses. The antidepressant activity of the synthesized compounds (4a-p) was evaluated by Forced swim test in rats and their neurotoxicity was evaluated by the rotarod test. Test compounds and clomipramine were administered intraperitoneally at dose of 100 mg/kg and 20 mg/kg respectively. Preliminary antidepressant screening of compounds (4a-p) revealed that compounds 4b, 4c, 4d, 4e, 4i and 4o significantly (P<0.01) reduces the duration of immobility time. These compounds were also tested in-vitro for MAO inhibitory effect. All the compounds were also screened for antifungal activity against Aspergillus niger MTCC 281, Aspergillus flavus MTCC 277, Monascus purpureus MTCC 369 and Penicillium citrinum NCIM 768 strains.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, New Delhi 110062, India. sureshkr.2006@gmail.com
authors.forename: Suresh
authors.initials: S
authors.lastname: Kumar
authors.forename: Sandhya
authors.initials: S
authors.lastname: Bawa
authors.forename: Sushma
authors.initials: S
authors.lastname: Drabu
authors.forename: Himanshu
authors.initials: H
authors.lastname: Gupta
authors.forename: Lalit
authors.initials: L
authors.lastname: Machwal
authors.forename: Rajiv
authors.initials: R
authors.lastname: Kumar
mesh_terms: D000818:Animals; D000928:Antidepressive Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects; D001234:Aspergillus niger / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D032741:Monascus / Q000187:drug effects; D008995:Monoamine Oxidase / Q000378:metabolism; D009043:Motor Activity / Q000187:drug effects*; D010407:Penicillium / Q000187:drug effects; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D051381:Rats; D017208:Rats, Wistar; D045442:Rotarod Performance Test; D013237:Stereoisomerism; D013315:Stress, Psychological / Q000188:drug therapy*; D013329:Structure-Activity Relationship; D013550:Swimming
chemical_list: C558523:2-chloro-8-methylquinolineamine; D000928:Antidepressive Agents; D000935:Antifungal Agents; D004791:Enzyme Inhibitors; D011804:Quinolines; D008995:Monoamine Oxidase