Singh P., Raj R., Singh P., Gut J., Rosenthal P.J., Kumar V.
Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India; Department of Chemistry, Durban University of Technology, Durban 4000, South Africa; Department of Medicine, University of California, San Francisco, CA, United States
Singh, P., Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India; Raj, R., Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India; Singh, P., Department of Chemistry, Durban University of Technology, Durban 4000, South Africa; Gut, J., Department of Medicine, University of California, San Francisco, CA, United States; Rosenthal, P.J., Department of Medicine, University of California, San Francisco, CA, United States; Kumar, V., Department of Chemistry, Guru Nanak Dev University, Amritsar 143005, Punjab, India
The manuscript pertains to the synthesis of urea/oxalamide tethered β-lactam-7-chloroquinoline conjugates with well modulated chain lengths and their antimalarial evaluation. The results reveal the dependence of activity profiles on the N-1 substituent of the β-lactam ring, the nature of the linker as well as the length of the alkyl chain. The most potent of the tested compounds showed an IC50 of 34.97 nM against chloroquine resistant W2 strain of Plasmodium falciparum. © 2013 Elsevier Masson SAS. All rights reserved.
(1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) carbamic acid ethyl ester; (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) carbamic acid ethyl ester; 1 [2 (7 chloro quinolin 4 ylamino) ethyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [2 (7 chloro quinolin 4 ylamino) ethyl] 3 (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) urea; 1 [3 (7 chloro quinolin 4 ylamino) propyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [3 (7 chloro quinolin 4 ylamino) propyl] 3 (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) urea; 1 [4 (7 chloro quinolin 4 ylamino) butyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [4 (7 chloro quinolin 4 ylamino) butyl] 3 (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) urea; 1 [6 ( 7 chloro quinolin 4 ylamino) hexyl] 3 (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) urea; 1 [6 (7 chloro quinolin 4 ylamino) hexyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; artemisinin; bleomycin; chloroquine; deethylamodiaquine; doxorubicin; n (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamic acid ethyl ester; n (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) oxalamic acid ethyl ester; n [1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] n' [4 (7 chloro quinolin 4 ylamino) butyl] oxalamide; n [1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] oxalamic acid ethyl ester; n [2 (7 chloro quinolin 4 ylamino) ethyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl oxalamide; n [2 (7 chloro quinolin 4 ylamino) ethyl] n' (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) oxalamide; n [3 (7 chloro quinolin 4 ylamino) propyl] n' (1 cyclohexyl 2 oxo 4-styry azetidin 3 oxalimide; n [4 (7 chloro quinolin 4 ylamino) butyl] n' (1 cyclohexyl 2 oxo 4 styryl azetiidn 3 oxalamide; n [6 (7 chloro quinolin 4 ylamino) hexyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 oxalamide; n[1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] n' [6 (7 chloro quinolin 4 ylamino) hexyl] oxalamide; n[3 (7 chloro quinolin 4 ylamino) propyl] n' (2 oxo 4 styryl 1 p tolyl azetidin 3 yl) oxalamide; quinine; quinoline derivative; unclassified drug; urea derivative; (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) carbamic acid ethyl ester; (2 oxo 4) styryl 1 4 tolyl azetidin 3 yl) carbamic acid ethyl ester; 1 [2 (7 chloro quinolin 4 ylamino) ethyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [2 (7 chloro quinolin 4 ylamino) ethyl] 3 (2 oxo 4 styryl 1 4 azetidin 3 yl) urea; 1 [3 (7 chloro quinolin 4 ylamino) propyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [3 (7 chloro quinolin 4 ylamino) propyl] 3 (2 oxo 4 styryl 1 4 azetidin 3 yl) urea; 1 [4 (7 chloro quinolin 4 ylamino) butyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [4 (7 chloro quinolin 4 ylamino) butyl] 3 (2 oxo 4 styryl 1 4 azetidin 3 yl) urea; 1 [6 (7 chloro quinolin 4 ylamino) hexyl] 3 (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) urea; 1 [6 (7 chloro quinolin 4 ylamino) hexyl] 3 (2 oxo 4 styryl 1 4 azetidin 3 yl) urea; antimalarial agent; artemisinin; beta lactam 7 chloroquinoline derivative; chloroquine; deethylamodiaquine; n (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamic acid ethyl ester; n (2 oxo 4 styryl 1 4 tolyl azetidin 3 yl) oxalamic acid ethyl ester; n [1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] n' [4 (7 chloro quinolin 4 ylamino) butyl] oxalamide; n [1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] n' [6 (7 chloro quinolin 4 ylamino) hexyl] oxalamide; n [1 (4 chloro phenyl) 2 oxo 4 styryl azetidin 3 yl] oxalamic acid ethyl ester; n [2 (7 chloro quinolin 4 ylamino) ethyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamide; n [2 (7 chloro quinolin 4 ylamino) ethyl] n' (2 oxo 4 styryl 1 4 tolyl azetidin 3 yl) oxalamide; n [3 (7 chloro quinolin 4 ylamino) propyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamide; n [3 (7 chloro quinolin 4 ylamino) propyl] n' (2 oxo 4 styryl 1 4 tolyl azetidin 3 yl) oxalamide; n [4 (7 chloro quinolin 4 ylamino) butyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamide; n [6 (7 chloro quinolin 4 ylamino) hexyl] n' (1 cyclohexyl 2 oxo 4 styryl azetidin 3 yl) oxalamide; oxalamide; quinine; urea; antimalarial activity; article; controlled study; drug conjugation; drug synthesis; human; human cell; IC 50; in vitro study; melting point; Plasmodium falciparum; proton nuclear magnetic resonance; thin layer chromatography; antimalarial drug resistance; Article; cytotoxicity; female; HeLa cell line; hydrogen bond; IC50; nonhuman; Antimalarial evaluation; Structure-activity relationship; Urea/oxalamide linker; β-Lactam-7-chloroquinoline conjugates; Antimalarials; beta-Lactams; Chloroquine; Humans; Malaria, Falciparum; Oxamic Acid; Plasmodium falciparum; Structure-Activity Relationship; Urea