957211-19-7Relevant academic research and scientific papers
Regio- and diastereoselective ring-opening of (S)-(-)-2-(trifluoromethyl) oxirane with chiral 2,5-disubstituted tetrahydroquinolines in hexafluoro-2-propanol
Li, Xun,Russell, Ronald K.,Chen, Hongfeng,Zhang, Yongzheng,Ballentine, Scott,Spink, Jan,Branum, Shawn,Liu, Fuqiang,Chen, Yanping,Rammeloo, Thomas,Aelterman, Wim,Sorgi, Kirk L.,Murray, William V.
, p. 1548 - 1551 (2010)
Multi-hundred grams of (S)-1,1,1-trifluoro-3-{(R)-2-[3-(1,1,2,2- tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-3,4-dihydroquinolin- 1(2H)-yl}propan-2-ol, a potent cholesteryl ester transfer protein (CETP) inhibitor, was prepared in quantitative isolated yield (>99%) with excellent chemical (>99% HPLC area%) and optical (>99% de) purities. The cornerstone to these results were achieved by regiospecific and diastereoselective ring-opening of optically pure (S)-(-)-2-(trifluoromethyl)oxirane (>99% ee) with (R)-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]- 1,2,3,4-tetrahydroquinoline (>99% ee) in hexafluoro-2-propanol at 22 °C for 24 h. This reaction did not require a rare earth metal salt (Yb(OTf) 3) as the catalyst nor a column chromatography for the purification. The excess (S)-(-)-2-(trifluoromethyl)oxirane and the solvent hexafluoro-2-propanol were recovered by distillation from the reaction and reused.
An efficient and scalable synthesis of (2R,αS)-3,4-dihydro-2-[3-(1,1, 2,2-tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-α- (trifluoromethyl)-1(2H)-quinolineethanol: A potent CETP inhibitor
Wang, Aihua,Zhang, Yan,Lu, Songfeng,Murray, William V.,Kuo, Gee-Hong
experimental part, p. 1406 - 1410 (2011/02/22)
An efficient and scalable synthesis of the potent CETP inhibitor, (2R,αS)-3,4-dihydro-2-[3-(1,1,2,2-tetrafluoroethoxy)phenyl] -5-[3-(trifluoromethoxy)phenyl]-α-(trifluoromethyl)-1(2H) -quinolineethanol 1, is described. One of the important intermediates,
Improved asymmetric synthesis of 3,4-dihydro-2-[3-(1,1,2,2- tetrafluoroethoxy)phenyl]-5-[3-(trifluoromethoxy)phenyl]-α- (trifluoromethyl)-1(2H)-quinolineethanol, a potent cholesteryl ester transfer protein inhibitor
Rano, Thomas A.,Kuo, Gee-Hong
supporting information; experimental part, p. 2812 - 2815 (2009/12/05)
The asymmetric synthesis of 3,4-dihydro-2-[3-(1,1,2,2-tetrafluoroethoxy) phenyl]-5-[3-(trifluoromethoxy)phenyl]-α-(trifluoromethyl)-1(2H) -quinolineethanol (compound 11), a cholesteryl ester transfer protein inhibitor, Is accomplished. The asymmetric cent
Design and synthesis of potent inhibitors of cholesteryl ester transfer protein (CETP) exploiting a 1,2,3,4-tetrahydroquinoline platform
Rano, Thomas A.,Sieber-McMaster, Ellen,Pelton, Patricia D.,Yang, Maria,Demarest, Keith T.,Kuo, Gee-Hong
scheme or table, p. 2456 - 2460 (2009/12/07)
Tetrahydroquinoline A is a potent inhibitor of the cholesterol ester transfer protein (CETP), a target for the treatment of low HDL-C and atherosclerosis. Low HDL-C has been identified as a key risk factor for cardiovascular disease in addition to high LD
Design, synthesis, and biological evaluation of (2R,αS)-3,4-dihydro- 2-[3-(1,1,2,2-tetrafluoroet-hoxy)phenyl]-5-[3-(trifluoromethoxy)-phenyl] -a-(trifluoromethyl)-1(2H)-quinolineethanol as potent and orally active cholesteryl ester transfer protein inhibi
Kuo, Gee-Hong,Rano, Thomas,Pelton, Patricia,Demarest, Keith T.,Gibbs, Alan C.,Murray, William V.,Damiano, Bruce P.,Connelly, Margery A.
experimental part, p. 1768 - 1772 (2010/03/01)
With the goal of identifying a CETP inhibitor with high in vitro potency and optimal in vivo efficacy, a conformationally constrained molecule was designed based on the highly potent and flexible 13. The synthetic chemistry efforts led to the discovery of
1,2,3,4-TETRAHYDRO-QUINOLINE DERIVATIVES AS CETP INHIBITORS
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Page/Page column 105-108, (2008/06/13)
The invention is directed to compounds of Formula (I) described herein useful as CETP inhibitors, compositions containing them, and methods of using them.
