529-37-3Relevant academic research and scientific papers
Unsymmetrical bisquinolines with high potency against P. falciparum Malaria
Burgess, Steven J.,Gunsaru, Bornface,Kelly, Jane X.,Li, Yuexin,Liebman, Katherine M.,Liebman, Michael C.,Morrill, Westin,Peyton, David H.
, (2020/05/18)
Quinoline-based scaffolds have been the mainstay of antimalarial drugs, including many artemisinin combination therapies (ACTs), over the history ofmoderndrugdevelopment. Althoughmuch progress has beenmade in the search for novel antimalarial scaffolds, itmay be that quinolineswill remain useful, especially if very potent compounds fromthis class are discovered. We report here the results of a structure-activity relationship(SAR) study assessingpotentialunsymmetrical bisquinoline antiplasmodial drug candidates using in vitro activity against intact parasites in cell culture. Many unsymmetrical bisquinolineswere found to be highly potent against both chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum parasites. Further work to develop such compounds could focus on minimizing toxicities in order to find suitable candidates for clinical evaluation.
Gas-phase pyrolysis in organic synthesis: Rapid green synthesis of 4-quinolinones
Al-Awadi, Nouria A.,Abdelhamid, Ismail Abdelshafy,Al-Etaibi, Alya M.,Elnagdi, Mohamed Hilmy
, p. 2205 - 2208 (2008/02/10)
Gas-phase pyrolysis of aminomethylene Meldrum's acid derivatives gave quinolinones and/or amines depending on the nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate. Georg Thieme Verlag Stuttgart.
Probing the TiO2 photocatalytic mechanisms in water purification by use of quinoline, photo-fenton generated OH. radicals and superoxide dismutase
Cermenati, Laura,Pichat, Pierre,Guillard, Chantal,Albini, Angelo
, p. 2650 - 2658 (2007/10/03)
In an attempt to improve our understanding of the basic mechanisms of the degradation of aromatic pollutants in water by TiO2 photocatalysis, quinoline (benzo[b]pyridine) was selected as a molecular probe, principally because of the difference in electron density over its two rings. This study was based on the identification and quantification of the primary products or principal secondary products of quinoline degradation either by TiO2 photocatalysis at pH 3 and 6 or by OH. radicals generated via the photo-Fenton reaction (Fe(II/III)-H2O2-UV) at pH 3. In this latter case, the three major products were those expected from the preferential electrophilic attack of OH. radicals on the electron-richer benzene moiety, viz., 5-, and 8-hydroxyquinolines and quinoline-5,8-dione derived from them. TiO2 photocatalysis did not yield this dione, and at the same percentages of degraded quinoline, the amounts of 5-hydroxyquinoline were lower by a factor of ca. 2 at pH 3 and ca. 10 at pH 6 (those of the 8-isomer were also decreased but no accurate measurements were obtained). In addition, at pH 6, we observed marked increases in the amounts of products corresponding to the oxidation of the pyridine moiety, viz., 4-quinolinone and especially 2-aminobenzaldehyde (the major product) and its N-formyl derivative. These results show that oxidative steps in TiO2 photocatalysis do not involve only OH. radicals. It was also observed that, at pH 6, superoxide dismutase (SOD), which catalyzes the elimination of O2.- species, decreased the TiO2 photocatalytic rate of quinoline disappearance, almost suppressed the formation of 2-aminobenzaldehyde, and lowered the amount of 4-quinolinone. The SOD and pH effects suggest a mechanism involving quinoline activation by hole transfer, followed by superoxide addition to the resulting radical cation. The nucleophilic character of superoxide implies addition to the pyridine moiety, i.e., with a regioselectivity opposite that of the OH. radical pathway.
Thermolysis of Polyazapentadienes. Part 9. Gas Phase Thermolysis of Some Dienamines, Enaminones, and Enaminothiones
Hickson, Clare L.,McNab, Hamish
, p. 339 - 342 (2007/10/02)
Thermolysis of the title compounds gives low yields of pyrroles by hydrogen-transfer-cyclisation-aromatisation sequence.The results are best explained by a dipolar mechanism for the hydrogen-transfer step: competitive aromatisation routes account for the range of substituted pyrroles which were obtained.
Process for the preparation of 4-amino-chloroquinolines
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, (2008/06/13)
4-Amino-chloroquinolines of the formula: STR1 in which R1 represents a hydrogen atom or an alkyl radical (1 to 5 carbon atoms), and R2 represents an alkyl radical (1 to 5 carbon atoms) optionally substituted by a dialkylamino group, or a phenyl radical optionally substituted by one or more carboxy and hydroxy radicals and alkyl radicals (1 to 4 carbon atoms) optionally substituted by a dialkylamino group, are prepared by the condensation of an amine of the formula: STR2 with a chloro-1,2,3,4-tetrahydroquinolin-4-one of the formula: STR3 with aromatization of the tetrahydroquinoline, the reaction being carried out in the presence of a ruthenium based catalyst on a support. The 4-amino-chloroquinoline products are useful as pharmaceuticals.
TOTAL REACTIVITY OF PYRIDINE AND QUINOLINE VIA THE REACTIONS OF ARYLBENZOATES WITH HYDROXIDE ION. APPARENT SUBSTITUENT CONSTANS FOR SOME N-HETEROAROMATIC GROUPS
Sawada, Masami,Ichihara, Masaharu,Ando, Takashi,Yukawa, Yasuhide,Tsuno, Yuho
, p. 4733 - 4736 (2007/10/02)
A new set of apparent ? values was evaluated for the aza substitution of all positions in pyridyl and quinolyl groups on the basis of the alkaline hydrolysis of aryl benzoates.The enhanced reactivities of 4-pyridyloxy- and 4-quinolyloxy- groups were first estimated quantitatively.
