2-(3,4-二羟基苯基)-6,7-二羟基-4-羰基-4H-色烯-5-基β-D-吡喃葡萄糖苷

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3,4-二羟基苯基)-6,7-二羟基-4-羰基-4H-色烯-5-基β-D-吡喃葡萄糖苷
• 中文别名: 右索他洛尔盐酸盐
• 英文名称: (S)-(+)-sotalol hydrochloride
• 英文别名: (+)-Sotalol hydrochloride；hydron;N-[4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]methanesulfonamide;chloride
• 化学式: C₁₂H₂₀N₂O₃S*ClH
• 分子量: 308.829
• InChiKey: VIDRYROWYFWGSY-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  86.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-二羟基苯基)-6,7-二羟基-4-羰基-4H-色烯-5-基β-D-吡喃葡萄糖苷 、 、 扁桃酸 在 hydrochloride salt 作用下， 生成 索他洛尔
  参考文献：
  名称：

  US06281246B1

  摘要：

  公开号：
• 作为产物：
  描述：

  (S)-(+)-2-bromo-1-(4-nitrophenyl)ethanol 在 吡啶 、 5 % platinum on carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 40.0 ℃ 、3.0 MPa 条件下， 反应 77.0h， 生成 2-(3,4-二羟基苯基)-6,7-二羟基-4-羰基-4H-色烯-5-基β-D-吡喃葡萄糖苷
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017

文献信息

• Synthesis of (S)-(+)-sotalol and (R)-(−)-isoproterenol via a catalytic enantioselective Henry reaction
  作者：Gonzalo Blay、Víctor Hernández-Olmos、José R. Pedro

  DOI：10.1016/j.tetasy.2010.02.027

  日期：2010.3

  A unified approach for the synthesis of (S)-(+)-sotalol and (R)-(−)-isoproterenol has been developed. The enantioselective Henry reaction of the appropriate aldehyde in the presence of a camphor-derived amino pyridine–Cu(II) complex was the key step of the synthesis. The reduction of the nitro group to give the corresponding amino alcohols followed by reductive alkylation of the amine provided the

  已经开发了用于（S）-（+）-索他洛尔和（R）-（-）-异丙基肾上腺素的合成的统一方法。在樟脑衍生的氨基吡啶-Cu（II）配合物存在下，适当醛的对映选择性亨利反应是合成的关键步骤。硝基的还原得到相应的氨基醇，然后胺的还原烷基化为目标产物提供了高对映体过量。
• Oral pharmaceutical dosage forms for pulsatile delivery of an antiarrhythmic agent
  申请人：——

  公开号：US20020098232A1

  公开（公告）日：2002-07-25

  Novel pharmaceutical dosage forms provide for pulsatile delivery of an antiarrhythmic agent that releases the drug in spaced apart “pulses.” The dosage forms are comprised of first, second and optional third dosage units, with each dosage unit having a different drug release profile. The dosage forms may comprise capsules housing compressed tablets or drug-containing beads, granules, or particles or may comprise a single tablet with the first, second and optional third dosage units incorporated therein, or a “coated core” dosage form. Methods of treatment using the pharmaceutical dosage forms are provided as well.

  小说药物剂型提供了脉冲输送抗心律失常药物的方法，该药物以间隔“脉冲”释放。该剂型由第一、第二和可选的第三剂量单位组成，每个剂量单位具有不同的药物释放曲线。该剂型可以包括装有压缩片剂或含药颗粒、颗粒或粒子的胶囊，也可以包括将第一、第二和可选的第三剂量单位合并在一起的单一片剂或“包衣核心”剂型。还提供了使用药物剂型的治疗方法。
• A Short Synthesis of d-Sotalol
  作者：Patrick Smith、Paul R. Brodfuehrer、John L. Dillon、Purushotham Vemishetti

  DOI：10.1080/00397919508012672

  日期：1995.4

  Asymmetric synthesis of d-Sotalol (2) was accomplished by chiral homogenous hydrogenation of (4-isopropylaminoacetyl)methane-sulfonanilide hydrochloride (1).
• Antiarrhythmic class III process
  申请人：Bristol-Myers Squibb Company

  公开号：EP0127435B1

  公开（公告）日：1991-08-28
• PHARMACEUTICAL COMPOSITION COMPRISING A COMBINATION OF DEXTRO- AND LAEVO- ISOMERS OF SOTALOL
  申请人：Torrent Pharmaceuticals Ltd

  公开号：EP1146865A1

  公开（公告）日：2001-10-24