402616-41-5

Usage

Chemical Properties

Off-White Solid

Uses

A FTY720 derivative

InChI:InChI=1/C27H39NO4/c1-2-3-4-5-6-8-11-23-14-16-24(17-15-23)18-19-27(21-29,22-30)28-26(31)32-20-25-12-9-7-10-13-25/h7,9-10,12-17,29-30H,2-6,8,11,18-22H2,1H3,(H,28,31)

Upstream product

• 501-53-1 benzyl chloroformate 
• 162359-55-9 fingolimod 

Downstream Products

• 402616-43-7 2-phenyl-4-(benzyloxycarbonylamino)-4-(4-(octyl)phenyl)-1,3-dioxane 
• 402616-45-9 (+/-)-2-benzyloxycarbonylamino-2-benzyloxymethyl-4-(4-(octyl)phenyl)butanol 
• 402616-23-3 FTY 520P 
• 844497-70-7 5-benzyloxycarbonylamino-2-chloro-5-[2-(4-octylphenyl)ethyl]-2-oxo-2λ5-1,3,2-dioxaphosphinane 

Relevant academic research and scientific papers

Effects of phosphorylation of immunomodulatory agent FTY720 (fingolimod) on antiproliferative activity against breast and colon cancer cells

FTY720 (fingolimod), a novel immunosuppressant, was found to become biologically activated by phosphorylation into FTY720-1-phosphate (FTY720-P), which is a high-affinity agonist for sphingosine-1-phosphate (sphingosine-1-P)-receptors. FTY720 has also been reported to have a strong antitumor activity. The association between the phosphorylation of FTY720 and the growth inhibition of FTY720 against cancer cells are still not completely understood. In this study, we investigated the effects of FTY720, sphingosine, and their related compounds on the proliferation of human breast cancer cell lines (MCF-7, MDA-MB-231 and Sk-Br-3) and human colon cancer cell lines (HCT-116 and SW620). Non-phosphorylated FTY720, sphingosine and an FTY720 derivative, ISP-I-55, showed significant growth inhibition against these cells, with IC 50 values of 5-20 μM at 48 h post-drug treatment. We confirmed that FTY720 induces the activation of a major mitogen-activated protein kinase, JNK, without the activation of p38 and down-regulation of phospho-ERK in MCF-7 breast cancer cells. In contrast, the phosphorylated derivatives, FTY720-P and sphingosine-1-P, as well as a phosphinane FTY720 derivative, cFTY720-P, did not inhibit the growth of the cells in the concentration range of 5-50 μM, whereas FTY720-P and sphingosine-1-P slightly induced the growth of MCF-7 cells. Combining FTY720 with dimethylsphingosine, a sphingosine kinase inhibitor, augmented the inhibitory effect of FTY720. These results indicate that the antiproliferative activity of FTY720 does not result from its phosphorylation, either endogenous or exogenous.

Asymmetric synthesis and biological evaluation of the enantiomeric isomers of the immunosuppressive FTY720-phosphate

A practical asymmetric synthesis of both enantiomers of the immunosuppressive FTY720-phosphate (2) was accomplished, and the enantiomers were pharmacologically evaluated. Several lipases showed considerable activity and enantioselectivity for O-acylation

Synthesis, stereochemical determination and biochemical characterization of the enantiomeric phosphate esters of the novel immunosuppressive agent FTY720

The novel immunosuppressive agent FTY720 (1) is phosphorylated in vivo in a variety of species yielding an active metabolite that is an agonist of four of the five known G-protein-coupled sphingosine-1-phosphate (S1P) receptors. A synthesis amenable to pr

Phosphate derivatives as immunoregulatory agents

Immunoregulatory compounds are disclosed of the formula: and as well as the pharmaceutically acceptable salts and hydrates thereof, are disclosed. The compounds are useful for treating immune mediated diseases and conditions, such as bone marrow, organ and tissue transplant rejection. Pharmaceutical compositions and methods of use are included.