6848-19-7Relevant academic research and scientific papers
Discovery of orally available tetrahydroquinoline-based glucocorticoid receptor agonists
Hudson, Andrew R.,Higuchi, Robert I.,Roach, Steven L.,Adams, Mark E.,Vassar, Angela,Syka, Peter M.,Mais, Dale E.,Miner, Jeffrey N.,Marschke, Keith B.,Zhi, Lin
, p. 1697 - 1700 (2011)
A series of tetrahydroquinoline derivatives were synthesized and profiled for their ability to act as glucocorticoid receptor selective modulators. Structure-activity relationships of the tetrahydroquinoline B-ring lead to the discovery of orally availabl
A facile synthesis of 2,2,4-trisubstituted-1,2-dihydroquinolines catalyzed by zinc triflate under solvent-free conditions
Kundu, Dhiman,Kundu, Shrishnu Kumar,Majee, Adinath,Hajra, Alakananda
experimental part, p. 1186 - 1190 (2009/12/03)
An efficient process has been developed for the synthesis of 2,2,4-trisubstituted-1,2-dihydroquinolines in good yields through a simple one-pot condensation between anilines and ketones in the presence of zinc triflate as a catalyst at room temperature under solvent-free conditions.
Mild and convenient synthesis of 1,2-dihydroquinolines from anilines and acetone catalyzed by ytterbium(III) triflate in ionic liquids
Li, Yongshu,Wu, Chunlei,Huang, Jianliang,Su, Weike
, p. 3065 - 3073 (2007/10/03)
A mild, convenient, and efficient process has been developed for the synthesis of 2,2,4-trimethyl-1,2-dihydroquinolines by the reaction of anilines with acetone catalyzed by ytterbium(III) triflate [Yb(OTf)3] in ionic liquids. The catalyst and ionic liquids can be easily recovered and reused, making this method friendly and environmentally acceptable. Copyright Taylor & Francis Group, LLC.
Efficient microwave-assisted synthesis of quinolines and dihydroquinolines under solvent-free conditions
Ranu, Brindaban C.,Hajra, Alakananda,Dey, Suvendu S.,Jana, Umasish
, p. 813 - 819 (2007/10/03)
A convenient and efficient procedure for the synthesis of quinolines and dihydroquinolines has been developed by a simple one-pot reaction of anilines with alkyl vinyl ketones on the surface of silica gel impregnated with indium(III) chloride under microwave irradiation without any solvent.
2,4-Diamino-5-benzylpyrimidines and Analogues as Antibacterial Agents. 12. 1,2-Dihydroquinolylmethyl Analogues with High Activity and Specificity for Bacterial Dihydrofolate Reductase
Johnson, Jay V.,Rauckman, Barbara S.,Baccanari, David P.,Roth, Barbara
, p. 1942 - 1949 (2007/10/02)
Twelve 2,4-diamino-5-pyrimidines containing gem-dimethyl or fluoromethyl substituents at the 2-position of the dihydroquinoline ring were prepared by condensations of dihydroquinolines with 2,4-diamino-5-(hydroxymethyl)pyrimidine.The dihydroquinolines were produced from the reaction of anilines with mesityl oxide or fluoroacetone.In some cases, 1-aryl-2,4-dimethylpyrroles were obtained as byproducts.Most of these pyrimidines were highly inhibitory to Escherichia coli dihydrofolate reductase (DHFR) and also had high specificity for bacterial enzyme. 2,4-Diamino-5-methyl>pyrimidine (13) had an apparent Ki value for E. coli DHFR 13 times lower than that of the control, trimethoprim (1), and was 1 order of magnitude more selective for the bacterial enzyme.It had outstanding activity against Gram-positive organisms in vitro, as well as broad-spectrum antibacterial activity equivalent to that of 1.The results of in vivo testing will be reported elsewhere.The gem-dimethyl substituents of the dihydroquinoline derivatives are considered to be responsible for the high selectivity, as well as contributing to potent bacterial DHFR inhibition.Molecular models are presented which suggest the probable interactions with the bacterial enzyme.
