ANTIMALARIAL-DRUGS .60. SYNTHESIS, ANTIMALARIAL ACTIVITY, AND QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS OF TEBUQUINE AND A SERIES OF RELATED 5-[(7-CHLORO-4-QUINOLINYL)AMINO]-3-[(ALKYLAMINO)METHYL][1,1'-BIPHENYL]-2-OLS AND N-OMEGA-OXIDES1,2
A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[alkylamino)methyl][1,1''-biphenyl]-2-ols and N.omega.-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1''-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[...
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Published in | Journal of medicinal chemistry Vol. 29; no. 6; pp. 924 - 939 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
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Amer Chemical Soc
01.06.1986
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Abstract | A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[alkylamino)methyl][1,1''-biphenyl]-2-ols and N.omega.-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1''-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1''-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N.omega.-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (.SIGMA. MR) and electron donation (.SIGMA..sigma.) of the phenyl ring substituents. A significant correlation with N.omega.-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man. |
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AbstractList | A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[alkylamino)methyl][1,1''-biphenyl]-2-ols and N.omega.-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1''-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1''-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N.omega.-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (.SIGMA. MR) and electron donation (.SIGMA..sigma.) of the phenyl ring substituents. A significant correlation with N.omega.-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man. |
Author | HUNG, JH ORTWINE, DF JOHNSON, JL MCNAMARA, DJ WORTH, DF ELSLAGER, EF WERBEL, LM KESTEN, SJ COOK, PD |
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RATIONAL AND SELF-CONSISTENT DATA BANK publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: NORRINGTON, FE |
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Snippet | A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[alkylamino)methyl][1,1''-biphenyl]-2-ols and N.omega.-oxides was prepared from the substituted... |
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Title | ANTIMALARIAL-DRUGS .60. SYNTHESIS, ANTIMALARIAL ACTIVITY, AND QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS OF TEBUQUINE AND A SERIES OF RELATED 5-[(7-CHLORO-4-QUINOLINYL)AMINO]-3-[(ALKYLAMINO)METHYL][1,1'-BIPHENYL]-2-OLS AND N-OMEGA-OXIDES1,2 |
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