Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate | 117752-80-4

• 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
• 英文名称: Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate
• 英文别名: ethyl 3-(5-chloro-2-methylindol-3-yl)propionate；ethyl 3-(5-chloro-2-methyl-1H-indol-3-yl)propanoate
• CAS: 117752-80-4
• 化学式: C₁₄H₁₆ClNO₂
• 分子量: 265.74
• InChiKey: UJXOPTKMCYBXNK-UHFFFAOYSA-N

物化性质

• 沸点：
  410.2±40.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate 在 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-(1-二苯甲基-5-氯-2-甲基吲哚-3-基)丙酸
  参考文献：
  名称：

  Inhibition of Cytosolic Phospholipase A₂α: Hit to Lead Optimization

  摘要：

  Compound I was previously reported to be a potent inhibitor of cPLA,(x in both artificial monomeric substrate and cell-based assays. However, I was inactive in whole blood assays previously used to characterize cyclooxygenase and lipoxygenase inhibitors. The IC(50) of 1 increased dramatically with cell number or lipid/detergent concentration. In an attempt to insert an electrophilic ketone between the indole and benzoic acid moieties, we discovered that increasing the distance between the two moieties gave a compound with activity in the GLU (7-hydroxycoumarinyl-gamma-linolenate) micelle assay, which contains lipid and detergent. Extensive structure-activity relationship work around this lead identified a potent pharmacophore for cPLA a inhibition. The IC(50)s between the GLU micelle and rat whole blood assays correlated highly. No correlation was found for other parameters, including lipophilicity or acidity of the required acid functionality. Compounds 25, 39, and 94 emerged as potent, selective inhibitors of cPLA(2)alpha and represent well-validated starting points for further optimization.

  DOI：

  10.1021/jm0507882
• 作为产物：
  描述：

  (E)-3-(5-Chloro-2-methyl-1H-indol-3-yl)-acrylic acid ethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以65%的产率得到Ethyl 5-chloro-2-methyl-1H-indole-3-propanoate
  参考文献：
  名称：

  1H-吲哚衍生物作为钙拮抗剂

  摘要：

  合成了两个具有 1H-吲哚骨架的短系列化合物，分别带有乙内酰脲和哌嗪核。测试了这两个系列中的一些化合物对 K + 去极化平滑肌（兔耳廓动脉和豚鼠绦虫）的钙拮抗活性及其对豚鼠心脏心房肌的负性肌力作用。

  DOI：

  10.1002/ardp.19883210702

文献信息

• Hypoglycemic imidazoline compounds
  申请人：ELI LILLY AND COMPANY

  公开号：EP1266897A3

  公开（公告）日：2003-12-03

  This invention relates to certain novel imidazoline compounds and analogues thereof, to their use for the treatment of diabetes, diabetic complications, metabolic disorders, or related diseases where impaired glucose disposal is present, to pharmaceutical compositions comprising them, and to processes for their preparation.The compounds have the following formula: whereinX is -O-, -S-, or -NR5-;R5 is hydrogen, C1-8 alkyl, or an amino protecting group;R4 isY is -O-, -S-, or -NR8-;Y' is -O- or -S-;

  本发明涉及某些新型的咪唑啉化合物及其类似物，以及它们用于治疗糖尿病、糖尿病并发症、代谢紊乱或相关疾病中的糖利用受损情况，涉及包含它们的药物组合物，以及它们的制备过程。这些化合物的公式如下：其中X是-O-，-S-，或-NR5-；R5是氢，C1-8烷基，或氨基保护基团；R4是Y是-O-，-S-，或-NR8-；Y'是-O-或-S-；