177259-72-2Relevant academic research and scientific papers
Synthesis and immunosuppressive activity of 2-substituted 2- aminopropane-1,3-diols and 2-aminoethanols
Kiuchi, Masatoshi,Adachi, Kunitomo,Kohara, Toshiyuki,Minoguchi, Masanori,Hanano, Tokushi,Aoki, Yoshiyuki,Mishina, Tadashi,Arita, Masafumi,Nakao, Noriyoshi,Ohtsuki, Makio,Hoshino, Yukio,Teshima, Koji,Chiba, Kenji,Sasaki, Shigeo,Fujita, Tetsuro
, p. 2946 - 2961 (2007/10/03)
A series of 2-substituted 2-aminopropane-1,3-diols was synthesized and evaluated for their lymphocyte-decreasing effect and immunosuppressive effect on rat skin allograft. A phenyl ring was introduced into the alkyl chain of the lead compound 3, which is an immunosuppressive agent structurally simplified from myriocin (1, ISP-I) via compound 2. The potency of the various compounds was dependent upon the position of the phenyl ring within the alkyl side chain. The most suitable length between the quaternary carbon atom and the phenyl ring was two carbon atoms. 2-Substituted 2-aminoethanols were successively synthesized and evaluated for their T-cell-decreasing effect and immunosuppressive effect using a popliteal lymph node gain assay in rats. The absolute configuration at the quaternary carbon affected the activity, and the (pro-S)-hydroxymethyl group of compound 6 was essential for potent immunosuppressive activity. Favorable substituents for the (pro-R)- hydroxymethyl group of 6 were hydroxyalkyl (hydroxyethyl and hydroxypropyl) or lower alkyl (methyl and ethyl) groups. 2-Amino-2-[2-(4- octylphenyl)ethyl]propane-1,3-diol hydrochloride (6, FTY720) was found to possess considerable activity and is expected to be useful as an immunosuppressive drug for organ transplantation.
Benzene compound and pharmaceutical use thereof
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, (2008/06/13)
A benzene compound of the formula STR1 wherein each symbol is as defined in the specification; an optically active isomer or salt thereof, a medicinal composition containing the same, and an immunosuppressant containing the same as the active ingredient. The compound, optically active isomer or salt has an excellent immunosuppressive effect and is useful as an inhibitor for the rejection reaction occurring in organ or bone marrow transplantation, and as a preventive or remedy for articular rheumatism, atopic eczema (dermatitis), Beh.cedilla.et's disease, uveal disease, systemic lupus erythematosus, Sjogren's syndrome, multiple sclerosis, myasthenia gravis, type I diabetes, endocrine ophthalmopathy, primary biliary, cirrhosis, Crohn's disease, glomerulonephritis, sarcoidosis, psoriasis, pemphigus, aplastic anemia, idiopathic thrombocytopenic purpura, allergy, polyarteritis nodosa, progressive systemic sclerosis, mixed connective-tissue disease, aortitis syndrome, polymyositis, dermatomyositis, Wegener's granuloma, ulcerative colitis, active chronic hepatitis, autoimmune hemolytic anemia, Evans' syndrome, bronchial asthma and pollinosis. It is useful also as an antifungal agent and hair growth stimulant.
Synthesis and biological evaluation of 2,2-disubstituted 2-aminoethanols: Analogues of FTY720
Kiuchi, Masatoshi,Adachi, Kunitomo,Kohara, Toshiyuki,Teshima, Koji,Masubuchi, Yumi,Mishina, Tadashi,Fujita, Tetsuro
, p. 101 - 106 (2007/10/03)
Desymmerization of symmetric FTY720 by substitution of different alkyl groups for one of the prochiral hydroxymethyl groups was performed. The size of the alkyl groups and the absolute configuration at quaternary carbon were important on immunosuppressive activity.
