【结 构 式】 |
【药物名称】RIG-200 【化学名称】2-(N-Acetyl-S-nitroso-D-penicillamido)-2-deoxy-1,3,4,6-tetra-O-acetyl-beta-D-glucopyranose 【CA登记号】202656-49-3 【 分 子 式 】C21H31N3O12S 【 分 子 量 】549.55812 |
【开发单位】University of St. Andrews (Originator) 【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, Restenosis Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Vasodilators, Nitric Oxide Donors |
合成路线1
Condensation of glucosamine (I) with anisaldehyde (II) gave imine (III). Subsequent acetylation of (III) with Ac2O in pyridine produced the tetra O-acetate (IV). The imine group of (IV) was then hydrolyzed with HCl in aqueous acetone to afford, after basic work-up, glucosamine tetraacetate (V), which was coupled with N-acetyl penicillamine using 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate to yield amide (VII). Finally, nitrosation of the mercapto group of (VII) with NaNO2 and HCl furnished the title compound.
【1】 Butler, A.R.; Megson, I.L.; Greig, I.R. (University of St. Andrews); Nitric oxide donor drugs. WO 9820015 . |
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) | 24036 | (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol; Glucosamine | 3416-24-8 | C6H13NO5 | 详情 | 详情 |
(II) | 27251 | 4-methoxybenzaldehyde; Anisicaldehyde; p-anisaldehyde | 123-11-5 | C8H8O2 | 详情 | 详情 |
(III) | 27252 | (3R,4R,5S,6R)-6-(hydroxymethyl)-3-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-2,4,5-triol | C14H19NO6 | 详情 | 详情 | |
(IV) | 27253 | (2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-[[(E)-(4-methoxyphenyl)methylidene]amino]tetrahydro-2H-pyran-3-yl acetate | C22H27NO10 | 详情 | 详情 | |
(V) | 27254 | (2R,3R,4R,5R,6S)-4,6-bis(acetoxy)-2-[(acetoxy)methyl]-5-aminotetrahydro-2H-pyran-3-yl acetate | C14H21NO9 | 详情 | 详情 | |
(VI) | 27255 | (2S)-2-(acetamido)-3-methyl-3-sulfanylbutyric acid | 59-53-0 | C7H13NO3S | 详情 | 详情 |
(VII) | 27256 | (2R,3R,4R,5R,6S)-5-[[(2S)-2-(acetamido)-3-methyl-3-sulfanylbutanoyl]amino]-4,6-bis(acetoxy)-2-[(acetoxy)methyl]tetrahydro-2H-pyran-3-yl acetate | C21H32N2O11S | 详情 | 详情 |