7-bromo-9-chloro-6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one | 689224-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-bromo-9-chloro-6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one
• CAS: 689224-55-3
• 化学式: C₂₁H₂₂BrClO₆
• 分子量: 485.759
• InChiKey: NHAWATPTFGGKEO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-bromo-9-chloro-6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one 在 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 7-Methyl-bicyclo[2.2.1]heptane-7-carboxylic acid 4-chloro-9-((S)-1-hydroxy-3-methyl-butyl)-8-methoxy-2,3-dimethyl-7-oxo-5H,7H-6,12-dioxa-dibenzo[a,d]cycloocten-1-yl ester
  参考文献：
  名称：

  Dibenzodioxocinones—A new class of CETP inhibitors

  摘要：

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.073
• 作为产物：
  描述：

  青霉素 在 N-氯代丁二酰亚胺 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铁 作用下， 以 乙醇 为溶剂， 生成 7-bromo-9-chloro-6-hydroxy-2-[(1S)-1-hydroxy-3-methylbutyl]-1-methoxy-8-methyl-10H-benzo[b][1,5]benzodioxocin-12-one
  参考文献：
  名称：

  Dibenzodioxocinones—A new class of CETP inhibitors

  摘要：

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.073

文献信息

• 7H-dibenzo[b,g][1,5]dioxocin-5-one derivatives and use thereof
  申请人：Bischoff Hilmar

  公开号：US20060247303A1

  公开（公告）日：2006-11-02

  The present invention relates to substituted 7H-dibenzo[b,g][1,5]dioxocin-5-one-derivatives, to processes for their preparation and to their use in medicaments, in particular as inhibitors of the cholesterol ester transfer protein (CETP) for the treatment and/or prevention of cardiovascular disorders, in particular hypolipoproteinaemia, dyslipidaemias, hypertriglyceridaemias, hyperlipidaemias and arteriosclerosis.

  本发明涉及取代的7H-二苯并[b，g][1,5]二氧杂环戊烷-5-酮衍生物，其制备过程以及它们在药物中的应用，特别是作为胆固醇酯转移蛋白（CETP）的抑制剂，用于治疗和/或预防心血管疾病，特别是低脂蛋白血症，脂质代谢异常，高三酰甘油血症，高脂血症和动脉硬化。
• Dibenzodioxocinones—A new class of CETP inhibitors
  作者：David Brückner、Frank-Thorsten Hafner、Volkhart Li、Carsten Schmeck、Joachim Telser、Alexandros Vakalopoulos、Gabriele Wirtz

  DOI：10.1016/j.bmcl.2005.05.073

  日期：2005.8

  Derivatives of the natural product 11-hydroxy-3-[(S)-1-hydroxy-3-methylbutyl]-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one 1 were studied as novel CETP inhibitors. Compound 2 was identified from HTS as a micromolar inhibitor. The compound suffered from very low stability in plasma. Optimisation by partial synthesis started from 1 and led to low-nanomolar inhibitors with good stability in rat plasma. (c) 2005 Elsevier Ltd. All rights reserved.