Potential Antimalarials. V. 4-(7′-Trifluoromethylquinolin-4′-Ylamino)Phenols, 4-[2′,7′ and 2',8′-Bis(Trifluoromethyl)Quinolin-4′-Ylamino]Phenols and N4-Substituted 2,7-(and 2,8-)Bis(Trifluoromethyl)-Quinolin-4-Amines

1985 ◽  
Vol 38 (12) ◽  
pp. 1827 ◽  
Author(s):  
GB Barlin ◽  
WL Tan
Keyword(s):  
Single Dose ◽  
Antimalarial Activity ◽  
Mannich Bases ◽  
Side Chains ◽  
Plasmodium Vinckei

Mono- and di-Mannich bases of 4-(7′-trifluoromethylquinolin-4′- ylamino )phenol and its 2′,7′- and 2′,8′-bis( trifluoromethyl ) analogues, for example 2,6-bis(piperidin-1′-ylmethyl)-4-(7′-trifluoromethyl- quinolin-4′-ylamino)phenol, have been prepared. The Mannich bases from 4-(7′-trifluoromethyl-quinolin-4′-ylamino)phenol showed significant antimalarial activity when injected intraperitoneally in a single dose of 100 mg/kg to mice infected with Plasmodium vinckei vinckei ; those from its 2′,7′- and 2′,8′-bis( trifluoromethyl ) analogues did not show appreciable activity. Some N4-substituted 2,7(and 2,8)- bis ( trifluoromethyl )quinolin-4-amines with aliphatic side chains were also prepared but were inactive. The blood schizontocidal activity of mefloquine was not retained in the 2,8-bis( trifluoromethyl )-quinolin-4-amines prepared here.

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. 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.

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. II. N4-Substituted 2-Methoxy(and 2-hydroxy)-1,5-naphthyridin-4-amines

1984 ◽  
Vol 37 (12) ◽  
pp. 2469 ◽  
Author(s):  
GB Barlin ◽  
W Tan
Keyword(s):  
Hydrogen Chloride ◽  
Sodium Methoxide ◽  
Antimalarial Activity ◽  
In Vivo Screen ◽  
Plasmodium Vinckei

Several new N4-substituted 2-methoxy(and 2-hydroxy)-1,5-naphthyridin-4-amines have been prepared from ethyl 3-aminopyridine-2-carboxylate. 2,4-Dichloro-1,5-naphthyridine with methanolic sodium methoxide gave 4-chloro-2-methoxy-1,5-naphthyridine but with methanolic hydrogen chloride afforded 4-chloro-1,5-naphthyridin-2-ol. The N4-substituted 1,5-naphthyridin-4-amines showed no significant antimalarial activity compared to chloroquine or primaquine in a preliminary in vivo screen against Plasmodium vinckei vinckei in mice.

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. III. N4-Substituted 7-Bromo-1,5-naphthyridin-4-amines

1985 ◽  
Vol 38 (3) ◽  
pp. 459 ◽  
Author(s):  
GB Barlin ◽  
W Tan
Keyword(s):  
Single Dose ◽  
Nicotinic Acid ◽  
Nucleophilic Replacement ◽  
Plasmodium Vinckei

A series of new N4-substituted 7-bromo-1,5-naphthyridin-4-amines has been prepared from nicotinic acid through 3-bromo-8-chloro- 1,5- naphthyridine by nucleophilic replacement of the 8-chloro substituent with appropriate amines. Several of these compounds, namely 7-bromo-N- (4′-diethylamino-1′-methylbutyl)-1,5-naphthy-ridin-4-amine (′5-azabromoquine'), 4-(7′-bromo-1′,5′-naphthyridin-4′-ylamino)-2-(diethylamino-methyl)phenol and 7-bromo-N-(2′-diethylaminoethyl)-1,5- naphthyridin-4-amine showed significant antimalarial acivity. Apparent cures were effected when these test chemicals were injected intra-peritoneally in a single dose of 200 mg/kg to mice infected with Plasmodium vinckei vinckei.

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.

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