183129-84-2Relevant academic research and scientific papers
Synthesis of fluorinated agonist of sphingosine-1-phosphate receptor 1
Aliouane, Lucie,Chao, Sovy,Brizuela, Leyre,Pfund, Emmanuel,Cuvillier, Olivier,Jean, Ludovic,Renard, Pierre-Yves,Lequeux, Thierry
, p. 4955 - 4960 (2014)
The bioactive metabolite sphingosine-1-phosphate (S1P), a product of sphingosine kinases (SphKs), mediates diverse biological processes such as cell differentiation, proliferation, survival and angiogenesis. A fluorinated analogue of S1P receptor agonist has been synthesized by utilizing a ring opening reaction of oxacycles by a lithiated difluoromethylphosphonate anion as the key reaction. In vitro activity of this S1P analogue is also reported.
Chiral vinylphosphonate and phosphonate analogues of the immunosuppressive agent FTY720
Lu, Xuequan,Sun, Chaode,Valentine, William J.,Shuyu,Liu, Jianxiong,Tigyi, Gabor,Bittman, Robert
supporting information; experimental part, p. 3192 - 3195 (2009/09/30)
The first enantioselective synthesis of chiral isosteric phosphonate analogues of FTY720 is described. One of these analogues, FTY720-(E)- vinylphosphonate (S)-5, but not its R enantiomer, elicited a potent antiapoptotic effect in intestinal epithelial ce
Enantioselective synthesis of the phosphate esters of the immunosuppressive lipid FTY720
Lu, Xuequan,Bittman, Robert
, p. 825 - 827 (2007/10/03)
The enantiomers of FTY720-phosphate (3) were synthesized via 2-methylene-4-(4-octylphenyl)butan-1-ol (7), 2,3-epoxy alcohol 8, and Δ2-oxazoline 10. These compounds have potential use in the treatment of autoimmune diseases and prevention of kid
Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: Pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system
Kawakami,Kitani,Yuasa,Abe,Moriwaki,Kagoshima,Terasawa,Tahara
, p. 683 - 692 (2007/10/03)
A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (±)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]- 6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4] diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.
