5-(环氧乙烷基甲氧基)-2,3,4,9-四氢咔唑 | 58457-32-2

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-(环氧乙烷基甲氧基)-2,3,4,9-四氢咔唑
• 中文别名: 卡维地洛杂质CY
• 英文名称: 1,2,3,4-tetrahydro-5-(2,3-epoxy-propoxy)-carbazole
• 英文别名: 5-(Oxiranylmethoxy)-2,3,4,9-tetrahydrocarbazole；5-(oxiran-2-ylmethoxy)-2,3,4,9-tetrahydro-1H-carbazole
• CAS: 58457-32-2
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: CVDBWNJRBIYYOX-UHFFFAOYSA-N

物化性质

• 熔点：
  96 - 98°C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  37.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(环氧乙烷基甲氧基)-2,3,4,9-四氢咔唑 以 乙醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 1,2,3,4-tetrahydro-5-(2-hydroxy-3-tert. butylamino-propoxy)-carbazole hydroacetate
  参考文献：
  名称：

  US3976779

  摘要：

  公开号：
• 作为产物：
  描述：

  5-羟基-2,3,4,9-四氢咔唑 、 环氧氯丙烷 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 5-(环氧乙烷基甲氧基)-2,3,4,9-四氢咔唑
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a

文献信息

• US3976779A
  申请人：——

  公开号：US3976779A

  公开（公告）日：1976-08-24
• Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release
  作者：Chris D. Smith、Aixia Wang、Kannan Vembaiyan、Jingqun Zhang、Cuihong Xie、Qiang Zhou、Guogen Wu、S. R. Wayne Chen、Thomas G. Back

  DOI：10.1021/jm401090a

  日期：2013.11.14

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.
• US3976779
  申请人：——

  公开号：——

  公开（公告）日：——