title: Synthesis and antimalarial activity study of some new Mannich bases of 7-chloro-4-aminoquinoline.
abstract: New derivatives of 7-chloro-4-aminoquinoline Mannich base were prepared by selectively modifying the aliphatic diethyl amino function of isoquine with different aliphatic/aromatic heterocyclic primary amino moieties at Mannich side chain. The synthesized compounds were characterized by their analytical and spectral data, and screened for in-vitro antimalarial activity against a chloroquine-sensitive 3D7 strain of Plasmodium falciparum. All the compounds showed in-vitro antimalarial activity at the tested dose; which, however, was considerably less than that of the standard reference drug, chloroquine. Among synthesized compounds, compounds with cyclohexyl (2f), methyl (2c) substitutions showed better activity than compounds substituted with n-octyl (2a), propyl (2b), 3-aminopropyl (2d) and furan-2- ylmethyl (2e) moieties at aminomethyl side chain. The results clearly demonstrate that the compound substituted with saturated cycloalkyl moiety (cyclohexyl) exhibited to some extent increased activity as compared to the compound containing heterocyclic moiety (furan-2-ylmethyl), and compounds with short chain alkyl substitutions (methyl, propyl) were found to be more active than that of compounds with long chain alkyl substitution (n-octyl).
authors.affiliation: Department of Pharmaceutical Sciences, Dibrugarh University, Dibrugarh, Assam, India. roy.susanta84@gmail.com
authors.forename: Susanta
authors.initials: S
authors.lastname: Roy
authors.forename: Dipak
authors.initials: D
authors.lastname: Chetia
authors.forename: Mithun
authors.initials: M
authors.lastname: Rudrapal
authors.forename: Anil
authors.initials: A
authors.lastname: Prakash
mesh_terms: D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000627:therapeutic use*; D008352:Mannich Bases / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects*; D013329:Structure-Activity Relationship
chemical_list: D000634:Aminoquinolines; D000962:Antimalarials; D008352:Mannich Bases; C047186:7-chloro-4-aminoquinoline