BIOMAT Database Logo BIOMAT Database Logo

Antimalarials. 11. 2-Vinylogs of substituted 2-aryl-4-quinoline amino alcohols. 1976

R E Lutz, and J M Sanders

3-(P-Chlorobenzylidene)-5, 7-dimethyl-2, 3-dihydro-1H-cyclopenta[b]quinoline-9-(di-n-butylaminomethyl)methanol and 2-[beta-(p-chlorostyryl)]-6, 8-dimethylquinoline-4-(di-n-butylaminomethyl)methanol were synthesized from 6, -8-dimethyl-4-hydroxycarbostyril by 3, 3-dichlorination, dimethoxylation th the 3-ketal, basic hydrolysis to the glyoxal acetal, Pfitzinger condensation with cylopentanone or acetone to the 2, 3-trimethylene or 2-methylquinoline, condensation with p-ClPhCHO at the 2-methylene or 2-methyl group, hydrolysis to the 4-quinaldehyde, methylenation to the epoxide, and condensation with Bu2NH. Both were curative against P. berghei in mice. The first was the more effective: active at 10 mg/kg, completely curative at 40 mg/kg, and only mildly phototoxic in animals.

UI MeSH Term Description Entries
D008288 Malaria A protozoan disease caused in humans by four species of the PLASMODIUM genus: PLASMODIUM FALCIPARUM; PLASMODIUM VIVAX; PLASMODIUM OVALE; and PLASMODIUM MALARIAE; and transmitted by the bite of an infected female mosquito of the genus ANOPHELES. Malaria is endemic in parts of Asia, Africa, Central and South America, Oceania, and certain Caribbean islands. It is characterized by extreme exhaustion associated with paroxysms of high FEVER; SWEATING; shaking CHILLS; and ANEMIA. Malaria in ANIMALS is caused by other species of plasmodia. Marsh Fever,Plasmodium Infections,Remittent Fever,Infections, Plasmodium,Paludism,Fever, Marsh,Fever, Remittent,Infection, Plasmodium,Plasmodium Infection
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D010962 Plasmodium berghei A protozoan parasite of rodents transmitted by the mosquito Anopheles dureni. Plasmodium bergheus,berghei, Plasmodium
D011804 Quinolines
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D000962 Antimalarials Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) Anti-Malarial,Antimalarial,Antimalarial Agent,Antimalarial Drug,Anti-Malarials,Antimalarial Agents,Antimalarial Drugs,Agent, Antimalarial,Agents, Antimalarial,Anti Malarial,Anti Malarials,Drug, Antimalarial,Drugs, Antimalarial
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014753 Vinyl Compounds Compounds containing the vinyl (-C Compounds, Vinyl
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus

Related Publications

R E Lutz, and J M Sanders
Antimalarials. 4. Trichloronaphthalene amino alcohols.
January 1979, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Antimalarials. 16. Synthesis of 2-substituted analogues of 8-[(4-amino-1-methylbutyl)amino]-6-methoxy-4-methyl-5-[3- (trifluoromethyl)phenoxy]quinoline as candidate antimalarials.
August 1989, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Antimalarials. 7-chloro-4-(substituted amino)quinolines.
April 1971, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Antimalarials. Substituted 2-phenyl-4-quinolinemethanols.
May 1968, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
[Studies on antimalarials. III. Synthesis of 2-(substituted styryl)-4-amino pyridines].
April 1983, Yao xue xue bao = Acta pharmaceutica Sinica,
R E Lutz, and J M Sanders
Antimalarials. 2. 2,6-Bis(aryl)-4-pyridinemethanols.
August 1972, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Antimalarials. 3. Benzothiazole amino alcohols.
March 1968, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Antimalarials. 5. 2-Aryl-6-trifluoromethyl-4-pyridinemethanols.
September 1973, Journal of medicinal chemistry,
R E Lutz, and J M Sanders
Design, synthesis and histamine H1-receptor antagonistic activity of some novel 4-amino-2-(substituted)-5-(substituted) aryl-6-[(substituted aryl) amino] pyrimidines.
January 2009, Arzneimittel-Forschung,
R E Lutz, and J M Sanders
Antimalarials; dl-7-chloro-2-(4-diethylamino-l-methylbutylamino)-quinoline.
July 1946, Journal of the American Chemical Society,
Copied contents to your clipboard!