Synthesis and Antimalarial Activity Study of Some New Mannich Bases of 7-Chloro-4-Aminoquinoline

2013 ◽  
Vol 9 (3) ◽  
pp. 379-383 ◽  
Author(s):  
Susanta Roy ◽  
Dipak Chetia ◽  
Mithun Rudrapal ◽  
Anil Prakash
Keyword(s):  
Antimalarial Activity ◽  
Mannich Bases

Potential Antimalarials. XVI. 4'-Chloro-3-[7″-chloro(and trifluoromethyl)quinolin-4″-yl]amino-5-(substituted amino)methylbiphenyl-4-ols and 4'-Bromo(and 3'-trifluoromethyl)-3-(substituted amino)methyl-5-(7″-trifluoromethylquinolin-4″-yl)aminobiphenyl-2-ols

1992 ◽  
Vol 45 (11) ◽  
pp. 1845 ◽  
Author(s):  
GB Barlin ◽  
FL Tian ◽  
B Kotecka ◽  
KH Rieckmann
Keyword(s):  
Plasmodium Falciparum ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
In Vitro Tests ◽  
Ic50 Values

Twenty-four mono-Mannich bases of the general formulae 4'-chloro-3-[7″-chloro(and trifluoro-methyl)quinolin-4'-yl]amino-5-(substituted amino)methylbiphenyl-4-ols and 4'-bromo(and 3'- trifluoromethyl-3(substituted amino)methyl-5(7″-trifluoromethylquinolin-4″-yl) aminobiphenyl-2-ols have been prepared by condensation of the 4-chloro heterocycle with 5-amino-3-(N-substituted amino)methyl-4'-chlorobiphenyl-4-ols or 5-amino-3-(N-substituted amino)methyl- 4'-bromo(or 3'-trifluoromethyl)biphenyl-2-ols. The antimalarial activity of these products in in vitro tests against Plasmodium falciparum reveals many with IC50 values of 50-100 nM ( chloroquine 20-40 nM ). The biphenyl-2-ols were more active than comparable biphenyl-4-ols.

Potential Antimalarials. IX. Di-mannich Bases of 4-(7′-trifluoro-methylquinazolin-4′-ylamino)phenol and 4-(7′-Trifluoromethylquinolin-4′-ylamino)phenol

1990 ◽  
Vol 43 (2) ◽  
pp. 311 ◽  
Author(s):  
GB Barlin ◽  
C Jiravinyu
Keyword(s):  
Plasmodium Falciparum ◽  
Antimalarial Activity ◽  
Mannich Bases

Syntheses are reported for a series of di-Mannich bases of 4-(7′-trifluoromethylquinazolin-4′-ylamino)phenol derived from 4-chloro-7-trifluoromethylquinazoline with the di-Mannich bases of 4-aminophenol. Some analogous quinolines were prepared similarly. When tested for antimalarial activity against Plasmodium falciparum in vitro, the quinazolines were rather less active than the corresponding quinolines.

Potential Antimalarials. XVII. Di- and Mono-Mannich Bases of 2(and 4)-[2(and 8)-Trifluoromethylquinolin-4-ylamino]phenol

1993 ◽  
Vol 46 (1) ◽  
pp. 21 ◽  
Author(s):  
GB Barlin ◽  
TMT Nguyen ◽  
B Kotecka ◽  
KH Rieckmann
Keyword(s):  
Plasmodium Falciparum ◽  
Mannich Base ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
Sensitive Strain ◽  
In Vitro Tests ◽  
Derivatives Of

Di- and mono-Mannich base derivatives of 2(and 4)-[2(and 8)-trifluoromethylquinolin-4-ylamino]phenols have been prepared for comparison with the 7-trifluoromethyl isomers in tests for antimalarial activity. The order of activity in in vitro tests against the FC-27 ( chloroquine -sensitive) strain of Plasmodium falciparum was 7-CF3 >> 8-CF3 > 2-CF3.

Potential Antimalarials. XV. Di-Mannich Bases of 2-(7'-Chloroquinolin-4'-ylamino)phenol and 2-[7'-Bromo( and trifluoromethyl)-1',5'-naphthyridin-4'-ylamino]phenol

1992 ◽  
Vol 45 (10) ◽  
pp. 1651 ◽  
Author(s):  
GB Barlin ◽  
TMT Nguyen ◽  
B Kotecka ◽  
KH Rieckmann
Keyword(s):  
Mannich Base ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
In Vitro Tests ◽  
In Vivo Tests ◽  
Methyl Derivatives ◽  
Derivatives Of ◽  
Plasmodium Vinckei

A total of 26 di-Mannich base derivatives of 2-(7'-chloroquinolin-4'-ylamino)phenol and 2-[7'- bromo (and trifluoromethyl )-1',5'-naphthyridin-4'-ylino]phenol, such as 2-(7'-chloroquinolin- 4'-ylamino)-4,6-bis( piperidin-1″-ylmethyl )phenol, together with some 3- and 5-methyl derivatives and mono-Mannich analogues, have been prepared by condensation of the 4-chloro heterocycle with the appropriate Mannich base derivatives of 2-aminophenols. In in vitro tests against Plasmodium falciparum, many of the di-Mannich base derivatives of 2-(7'-chloroquinolin-4'-ylarnino)phenol exhibited activity comparable to or superior to chloroquine against the chloroquine -sensitive (FCQ-27) isolate, and vastly superior activity compared with chloroquine against the chloroquine -resistant (K-1) isolate. Strong antimalarial activity was also revealed in in vivo tests against Plasmodium vinckei vinckei in mice.

ChemInform Abstract: Synthesis of Quinoline-Mannich Bases of Possible Antimalarial Activity.

1986 ◽  
Vol 17 (4) ◽  
Author(s):  
M. M. KAMEL ◽  
I. NABIH ◽  
M. E. NASR ◽  
M. M. ABBASI
Keyword(s):  
Antimalarial Activity ◽  
Mannich Bases

Potential Antimalarials. VI. Mannich-Bases Derived From 4-[7′-Bromo(and Chloro)-1′,5′-Naphthyridin-4′-Ylamino]Phenols and 4-(7′-Trifluoromethylquinolin-4′-Ylamino)Phenol

1986 ◽  
Vol 39 (1) ◽  
pp. 51 ◽  
Author(s):  
GB Barlin ◽  
WL Tan
Keyword(s):  
Single Dose ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
Plasmodium Vinckei

Eleven di-Mannich bases derived from 4-[7′-bromo(and chloro )-1′,5′-naphthyridin-4′-ylamino]phenols and 4-(7′-trifluoromethylquinolin-4′- ylamino )phenol have been prepared. Each of these compounds showed very good antimalarial activity w en injected intraperitoneally in a single dose of 50-100 mg/kg to mice infected with Plasmodium vinckei vinckei.

Potential Antimalarials. IV. 4-[7'-Bromo(and Chloro)-1′,5′-Naphthyridin-4′-Ylamino]Phenols and N4-Substituted 7-Chloro-1,5-Naphthyridin-4-Amines

1985 ◽  
Vol 38 (6) ◽  
pp. 905 ◽  
Author(s):  
G Barlin ◽  
W Tan
Keyword(s):  
Single Dose ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
Parasite Control ◽  
Plasmodium Vinckei

A series of nine mono- and di-Mannich bases, for example 4-(7′-bromo-1′,5′-naphthyridin-4′-ylamino)-2,6-bis( dimethylaminomethyl )phenol derived from 4-(7′-bromo-1′,5′-naphthyridin-4′-ylamino)phenol and several other N4-substituted 7-bromo- and 7-chloro-1,5-naphthyridin-4- amines have been prepared. ′All these compounds showed significant antimalarial activity when injected intraperitoneally in a single dose of 100-200 mg/kg to mice infected with Plasmodium vinckei vinckei. The di-Mannich bases appeared to be the most potent and effective in parasite control; however, no deaths were observed in infected mice treated with the mono- Mannich compounds.

Potential Antimalarials. XVIII. Some Mono- and Di-Mannich Bases of 3-[7-Chloro(and trifluoromethyl)quinolin-4-ylamino]phenol

1993 ◽  
Vol 46 (11) ◽  
pp. 1685 ◽  
Author(s):  
GB Barlin ◽  
SJ Ireland ◽  
TMT Nguyen ◽  
B Kotecka ◽  
KH Rieckmann
Keyword(s):  
Plasmodium Falciparum ◽  
Mannich Reaction ◽  
Mannich Base ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
Derivatives Of

Syntheses are reported for mono- and di-Mannich base derivatives of 3-[7-chloro(and trifluoro-methyl)quinolin-4-ylamino]phenols by Mannich reaction on 3-[7-chloro(and trifluoromethyl )-quinolin-4-ylamino]phenols or by condensation of Mannich base derivatives of 3-aminophenol, prepared from 3-nitrophenol, with the appropriate 4-chloroquinoline. The antimalarial activity of 3-(7′-chloroquinolin-4′-ylamino)-2,6-bis[ pyrrolidin-1″-ylmethyl -(or piperidin-1″-ylmethyl)]phenol against the FC-27 isolate of Plasmodium falciparum was comparable to that of chloroquine, and it was not significantly diminished in tests against the chloroquine -resistant K-1 isolate.

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