Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod).
نویسندگان
چکیده
The key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate (13), for the immunomodulatory agent FTY720 (2: fingolimod) was synthesized via Michael addition of diethyl(acetylamino)malonate (6) to 4-octanoylstyrene (12).
منابع مشابه
Crystal structure and identification of resonance forms of diethyl 2-(3-oxoiso-1,3-dihydrobenzofuran-1-ylidene)malonate
The reaction of diethyl malonate with phthaloyl chloride in aceto-nitrile in the presence of tri-ethyl-amine and magnesium chloride results in the formation of the title compound, diethyl 2-(3-oxo-1,3-di-hydro-2-benzo-furan-1-yl-idene)propane-dioate, C15H14O6. One of the ester groups of the diethyl malonate fragment is almost coplanar with the isobenzo-furan unit, while the plane of the other g...
متن کاملTransient T cell accumulation in lymph nodes and sustained lymphopenia in mice treated with FTY720.
FTY720 (2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride) is an orally available immunomodulatory agent that induces severe peripheral blood lymphopenia. Most studies of these lymphopenic effects have been limited to short-term exposure to FTY720. FTY720 alters the ability of lymphocytes to respond to sphingosine-1-phosphate (S1P) through S1P receptors, particularly S1P1. FTY720...
متن کاملAbsorption and disposition of the sphingosine 1-phosphate receptor modulator fingolimod (FTY720) in healthy volunteers: a case of xenobiotic biotransformation following endogenous metabolic pathways.
Fingolimod [(FTY720), Gilenya; 2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol], a new drug for the treatment of relapsing multiple sclerosis, acts through its phosphate metabolite, which modulates sphingosine 1-phosphate receptors. This represents a novel mechanism of action. In the present work, the absorption and disposition of (14)C-labeled fingolimod were investigated in healthy male vo...
متن کاملBrain penetration of the oral immunomodulatory drug FTY720 and its phosphorylation in the central nervous system during experimental autoimmune encephalomyelitis: consequences for mode of action in multiple sclerosis.
FTY720 [2-amino-2-[2-(4-octylphenyl) ethyl]propane-1,3-diol hydrochloride] is an oral sphingosine-1-phosphate receptor modulator under development for the treatment of multiple sclerosis (MS). The drug is phosphorylated in vivo by sphingosine kinase 2 to its bioactive form, FTY720-P. Although treatment with FTY720 is accompanied by a reduction of the peripheral lymphocyte count, its efficacy in...
متن کاملcatena-Poly[3,3′-diethyl-1,1′-(propane-1,3-diyl)di(1H-imidazol-3-ium) [silver(I)-di-μ-iodido-silver(I)-di-μ-iodido]]
The title compound, {(C(13)H(22)N(4))[Ag(2)I(4)]}(n), was prepared by reaction of 1,3-bis-(N-ethyl-imidazolium-1-yl)propane iodide with silver (I) oxide. In the 3,3'-diethyl-1,1'-(propane-1,3-di-yl)di(1H-imidazol-3-ium) cation, the dihedral angle between the imidazole rings is 49.3 (1)°. In the [Ag(2)I(4)](2-) anion, each Ag(I) atom is bonded to three iodide anions, the two Ag(I) atoms and two ...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical & pharmaceutical bulletin
دوره 56 4 شماره
صفحات -
تاریخ انتشار 2008