Erratum to “Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides” [Bioorg. Med. Chem. 17 (2009) 203–221]

Quinolines and structurally related heterocycles as antimalarials

“…The most potent compound, 48, a morpholino derivative (IC 50 ¼ 14.1 nM, FcB1R) cured mice infected by P. berghei, and exhibited lower toxicity than AQ upon mouse macrophages [77]. In order to complete the SAR study and optimize the second side chain in this 4-anilinoquinoline series, Sergheraert et al examined the antimalarial activity of carbamate (49) and amide (50) derivatives of 4-anilinoquinolines [78]. The amide and carbamate series were very similar except for the chain length, which was crucial for the amides but not for the carbamates.…”

“…Based upon the reports that the urea derivatives interact with the dihydrofolate reductase (DHFR) through hydrogen bonding [47], accumulate in the parasitic food vacuole and inhibit the plasmepsin of the parasite [48], Batra et al investigated the antimalarial efficacy and docking studies of 2-methyl-6-ureido-4-quinolinamides 22 on the PfDHFR [49]. Two of the analogues 22a and 22b exhibited IC 50 value of 0.4 ng/mL, 5-fold better than CQ.…”

Synthesis and evaluation of a novel series of quinoline derivatives with immunosuppressive activity

“…Purification through silica gel chromatography eluting with PE/EtOAc afforded corresponding compounds 10-13. (14)(15)(16) To a solution of 4 (205 mg, 1.0 mmol) in CH 2 Cl 2 (20 mL) and water (20 mL) was added sugar donor (1.5 mmol), NaOH (320 mg, 8.0 mmol) and TBAB (386 mg, 1.2 mmol). The suspension was stirred at 50°C for 18 h. Water (10 mL) was added and the aqueous layer was extracted with CH 2 Cl 2 (3 Â 20 mL).…”

“…15 Quinoline skeleton, found in many synthetic and natural products, is a class of heterocyclic compounds which possess a variety of biological activities, such as antimalarial, 16 antiinflammatory, 17,18 antibacterial, 19 antiviral, 20 antitubercular, 21 and antitumor. 22 However, the effect of quinoline and its derivatives on immunosuppressive activity have not been studied sufficiently.…”

Novel diaryl ureas with efficacy in a mouse model of malaria

“…4 We also reported in 2005 the preparation of triclosan-based 4'-ureas (Supplementary Data Figure S1) that were less potent against cultured parasite (EC 50 values of ~100 μM) than 12 -25, but exhibited IC 50 values of ~100 nM against purified PfFabI assayed in vitro. 14 More generally, the diaryl urea class of small molecules has been previously reported in the literature to exhibit potent efficacy against cultured parasites [21][22][23][24][25] but without definitive biological target identification. This chemotype was also found amongst hits against P. falciparum dihydroorotate dehydrogenase 26 that lacked whole-cell activity.…”