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- W2058804540 abstract "Abstract The increasing resistance of Plasmodium sp. parasites to the current drugs is the principal reason for the reemergence of malaria. As a consequence, the interest for new and effective drugs against resistant or multidrug-resistant Plasmodium strains has increased. This paper describes a molecular modeling study of the new 1H-pyrazolo[3,4-b]pyridine derivatives (4 [(3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-(2-piperidinyl)]methanol; 5 [(3-methyl-1-phenyl-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-(2-piperidinyl)]methanol; 6 [(3,6-dimethyl-1-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-(2-piridyl)]methanol; 7 3,6-dimethyl-1-phenyl-4-(2-pyridoyl)-1H-pyrazolo[3,4-b]pyridine and 8 3-methyl-1-phenyl-4-(2-pyridoyl)-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine) designed as isosters of the quinoline carbinolamine antimalarial, mefloquine (2). The minimal energy conformations of the erythro and monoprotonated compounds, obtained by the AM1 semiempirical method, show that the interatomic distances, bond angles and dihedral angles of 4 and 5 are close to those of 2 (AM1 and 3-21G∗ calculations) and of the X-ray crystal structures of mefloquine salts. The atomic superimposition of 4 and 5 with mefloquine revealed the 1H-pyrazolo[3,4-b]pyridine system to be coplanar with the mefloquine quinoline ring (RMS=0.06 A). Electronic similarities are observed between 4, 5 and 2 with respect to MEPs, HOMO and LUMO eigenvalues and coefficient distribution, molecular dipole moment and cation–π interaction. Comparable structural and electronic parameters were not observed for 6–8, which can be accounted for by the chemical modifications in the hydroxyl and in the piperidine moieties of the pharmacophore. In a manual docking study performed between 4–8 and heme, a probable molecular target of quinoline antimalarial drugs, only 4 and 5 showed the geometrical and energy requirements to effect the biological interaction. The stereoelectronic properties presented here correlate to previous qualitative structure–activity relationships on carbinolamine antimalarials and are in accordance to the recently identified isosteric relationship between the 1H-pyrazolo[3,4-b]pyridine system and the quinoline nucleus of mefloquine." @default.
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- W2058804540 date "2002-03-01" @default.
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- W2058804540 title "Molecular modeling of novel 1H-pyrazolo[3,4-b]pyridine derivatives designed as isosters of the antimalarial mefloquine" @default.
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- W2058804540 doi "https://doi.org/10.1016/s0166-1280(01)00677-7" @default.
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