• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【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
      1,3,4,6-Tetra-O-acetyl-2-[2(S)-(acetylamino)-3-methyl-3-(nitrososulfanyl)butyramido]-2-deoxy-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
Extended Information