4-Aminoquinoline-ferrocenyl-chalcone conjugates: Synthesis and anti-plasmodial evaluation.
A series of aliphatic and aromatic substituted 1H-1,2,3-triazole-tethered 4-amino-quinoline-ferrocenylchalcone conjugates has been synthesized and evaluated for anti-plasmodial activity. The conjugates with flexible aliphatic (aminoethanol or aminopropanol) substituents on the quinoline ring showed better anti-plasmodial activities compared to those with cyclic (piperazine or aminophenol) substituents. The conjugate 17j was the most potent and non-cytotoxic, with an IC50value of 0.37 μM against the chloroquine-resistant W2 strain of Plasmodium falciparum.
Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, Punjab, India.
Amandeep
A
Singh
Department of Medicine, University of California, San Francisco, CA, USA.
Jiri
J
Gut
Department of Medicine, University of California, San Francisco, CA, USA.
Philip J
PJ
Rosenthal
Department of Chemistry, Guru Nanak Dev University, Amritsar, 143005, Punjab, India. Electronic address: vipan_org@yahoo.com.
Vipan
V
Kumar
D000634:Aminoquinolines / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000494:pharmacology; D000977:Antiparasitic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002599:Chalcone / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004352:Drug Resistance, Microbial / Q000187:drug effects; D005296:Ferrous Compounds / Q000737:chemistry; D006801:Humans; D000075163:Metallocenes; D021261:Parasitic Sensitivity Tests; D010961:Plasmodium / Q000187:drug effects; D010963:Plasmodium falciparum / Q000187:drug effects; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry / Q000494:pharmacology
D000634:Aminoquinolines; D000962:Antimalarials; D000977:Antiparasitic Agents; D005296:Ferrous Compounds; D000075163:Metallocenes; D014230:Triazoles; D002599:Chalcone; C001920:4-aminoquinoline; C004998:ferrocene
1,3-dipolar cycloaddition; 4-Amino-quinoline-ferrocenylchalcone; Antiplasmodial activities; Structure-activity relationship