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【结 构 式】

【药物名称】SC-73770, M-40401

【化学名称】(PB-7-11-2344'3')-Dichloro[(4aR,6S,12S,13aR,17aR,21aR)-6,12-dimethyl-11,7-nitrilo-1,2,3,4,4a,5,6,12,13,13a,14,15,16,17,17a,18,19,20,21,21a-eicosahydro-7H-dibenzo[b,h][1,4,7,10]tetraazacycloheptadecine-kappaN5,kappaN13,kappaN18,kappaN21,kappaN22]manganese

【CA登记号】218791-28-7

【 分 子 式 】C23H39Cl2MnN5

【 分 子 量 】511.44478

【开发单位】MetaPhore (Originator), Pfizer (Originator)

【药理作用】CARDIOVASCULAR DRUGS, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Treatment of Shock, Superoxide Dismutases

合成路线1

Treatment of (R,R)-1,2-diaminocyclohexane (I) with triphenylmethyl chloride produced the N-trityl derivative (II). Subsequent condensation of (II) with glyoxal (III) gave the bis-imine (IV), which was reduced to amine (V) using LiBH4. Cleavage of the N-trityl groups of (V) with HCl in acetone afforded tetraamine (VI). This was then condensed with 2,6-diacetylpyridine (VII) in the presence of MnCl2 to furnish the cyclic bis-imine manganese complex (VIII). Finally, transfer hydrogenation of the imine functions of (VIII) using ammonium formate and Pd/C produced the cyclic pentaamino derivative as a diastereomeric mixture. The title isomer was then purified by separative partition between H2O and CH2Cl2.

1 Udipi, K.; Joardar, S.; Forster, D.; Riley, D.; Henke, S.; Brethaur, K.; Thurmond, B.; Ornberg, R. (Pharmacia Corp.); Biomaterials modified with superoxide dismutase mimics. WO 0072893 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11130 (1R,2R)-1,2-cyclohexanediamine; (1R,2R)-2-aminocyclohexylamine; cis-1,2-Diaminocyclohexane 20439-47-8 C6H14N2 详情 详情
(II) 48511 N-[(1R,2R)-2-aminocyclohexyl]-N-tritylamine; (1R,2R)-N(1)-trityl-1,2-cyclohexanediamine C25H28N2 详情 详情
(III) 32557 glyoxal; 2-oxoacetaldehyde 107-22-2 C2H2O2 详情 详情
(IV) 48512 (1R,2R)-N(1)-trityl-N(2)-((E)-2-[[(1R,2R)-2-(tritylamino)cyclohexyl]imino]ethylidene)-1,2-cyclohexanediamine; N-trityl-N-[(1R,2R)-2-[((E)-2-[[(1R,2R)-2-(tritylamino)cyclohexyl]imino]ethylidene)amino]cyclohexyl]amine C52H54N4 详情 详情
(V) 48513 (1R,2R)-N(1)-trityl-N(2)-(2-[[(1R,2R)-2-(tritylamino)cyclohexyl]amino]ethyl)-1,2-cyclohexanediamine; N-trityl-N-[(1R,2R)-2-[(2-[[(1R,2R)-2-(tritylamino)cyclohexyl]amino]ethyl)amino]cyclohexyl]amine C52H58N4 详情 详情
(VI) 48514 (1R,2R)-N(1)-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)-1,2-cyclohexanediamine; N-[(1R,2R)-2-aminocyclohexyl]-N-(2-[[(1R,2R)-2-aminocyclohexyl]amino]ethyl)amine C14H30N4 详情 详情
(VII) 48515 2,6-Diacetylpyridine 1129-30-2 C9H9NO2 详情 详情
(VIII) 48516 (4R,9R,14R,19R)-2,21-dimethyl-3,10,13,20,26-pentaazatetracyclo[20.3.1.0(4,9).0(14,19)]hexacosa-1(26),2,20,22,24-pentaene C23H35N5 详情 详情
Extended Information