Antimalarial potency of 2-benzoyl-4-quinolinemethanols

Synthesis, antimalarial activity, and phototoxicity of some benzo[h]quinoline-4-methanols

“…The following procedure for a-bromomethyl-2-(2,4-dimethylphenyl)-3-methylbenzo[h]quinolyl ketone (44) is typical. A solution of 41.0 g (0.12 mol) of the carboxylic acid (11) in 130 ml of SOCI2 was refluxed 2 h. The SOCI2 was removed in vacuo, and the residue was dissolved in dry Et2Ü (100 ml) and filtered and the EtaO evaporated. Dry CeHs (200 ml) was added and evaporated in vacuo.…”

“…59-67 (Table VII) I [8][9][10][11][12][13][14][15][16][17][18][19] (Table II) system. Several 2-unsubstituted 3-methyl candidate drugs were also prepared to evaluate this type of substitution in relation to phototoxicity and antimalarial activity.…”

“…In our continuing search for novel local anesthetics,1 we have synthesized and tested a number of oxindole-3spiropyrrolidines and -piperidines (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11). These compounds incorporate the principal structural moieties of the local anesthetic and antiarrhythmic drug lidocaine (12)-viz.…”

Copper‐Catalyzed ortho‐Functionalization of Quinoline N‐Oxides with Vinyl Arenes

“…Quinoline derivatives are known to have a wide application in pharmaceutical, agrochemical and industrial chemistry, which also serve as useful building blocks in synthetic organic chemistry . Especially, C2‐substituted quinoline derivatives have been found to exhibit various biological activities, such as CysLT 1 antagonist, antileishmanial activity, antimalarial activity and P‐selectin inhibitors for the treatment of atherosclerosis and deep vein thrombosis etc. (Figure ) .…”

Antimalarials. 9. .alpha.-(2-Piperidyl)-4-quinolinemethanols carrying 2-aroxy and 2-(p-chloroanilino) groups

“…2-Chloro-a-diethylaminomethyl-4-quinolinemethanol, synthesized by a conventional route, was "inactive" against P. berghei but active against Plasmodium gallinaceum in birds Syntheses of 12 a-(2-piperidyl)-4-quinolinemethanols (1 -12) (and incidentally the 2-chlorodiethylamino alcohols 13 and 14) were undertaken with the following expectations: that the 2-aroxy and 2-(p-chIoroanilino) would prevent oxidative biotransformations to less active carbostyryls;4 that these groups would lead to high activities against Plasmodium berghei in mice with firm binding of the molecules to the host tissues;5 and that phototoxicity, formerly thought to be associated with conjugation of aryl and the 2-quinoline nuclei6"8 in highly curative drugs such as 15,9 might be reduced by intervention between the aromatic nuclei of the heteroelement O or N which would destroy the direct conjugation although replacing it by forked conjugation. 10 Chemistry. The a-(2-piperidyl)methanols 1-12 were synthesized from appropriate isatins through 2-hydroxy-and 2chlorocinchoninic acids 16-20 (and ester 21).11"14 Rather than displacing the 2-Cl at this stage,11 the reactions outlined in Scheme I were used, namely, additions of 2-PyLi,15"19 then aroxy and anilino displacements of the active 2-Cl20 of the 2-pyridyl ketones [22][23][24][25][26] (more difficult when an 8 substituent was present), and simultaneous Pt-H2-AcOH17 hydrogenations of the keto and pyridyl groups of [27][28][29][30][31][32][33][34][35][36][37][38] 43, presumably because of catalyst poisoning by sulfur of the substrate.…”