Tert-butyl 1-[3-(4-decoxyphenoxy)-2-hydroxypropyl]indole-5-carboxylate | 741606-42-8

• 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: Tert-butyl 1-[3-(4-decoxyphenoxy)-2-hydroxypropyl]indole-5-carboxylate
• CAS: 741606-42-8
• 化学式: C₃₂H₄₅NO₅
• 分子量: 523.713
• InChiKey: IMBHWNWINYUTIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 1-[3-(4-decoxyphenoxy)-2-hydroxypropyl]indole-5-carboxylate 在 乙酸酐 、 二甲基亚砜 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 1-[3-(4-Decyloxyphenoxy)-2-oxopropyl]indole-5-carboxylic acid
  参考文献：
  名称：

  Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α

  摘要：

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.

  DOI：

  10.1021/jm051243a
• 作为产物：
  描述：

  2-[(4-(癸氧基)苯氧基)甲基]环氧乙烷 、 2-甲基-2-丙基1H-吲哚-5-羧酸酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Tert-butyl 1-[3-(4-decoxyphenoxy)-2-hydroxypropyl]indole-5-carboxylate
  参考文献：
  名称：

  Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α

  摘要：

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.

  DOI：

  10.1021/jm051243a

文献信息

• Novel heteroaryl-substituted acetone derivatives as inhibitors of phospholipase a2
  申请人：Lehr Matthias

  公开号：US20060142366A1

  公开（公告）日：2006-06-29

  The invention relates to novel heteroaryl substituted acetone derivatives which inhibit the enzyme phospholipase A 2 , pharmaceutical preparations containing these compounds and a method of producing these compounds.

  本发明涉及新型杂环取代丙酮衍生物，其抑制磷脂酶A2酶，包含这些化合物的药物制剂以及制备这些化合物的方法。
• NEUE HETEROARYLSUBSTITUIERTE ACETONDERIVATE ALS HEMMSTOFFE DER PHOSPHOLIPASE A sb 2 /sb
  申请人：MERCKLE GMBH

  公开号：EP1590324B1

  公开（公告）日：2009-03-11
• US7608633B2
  申请人：——

  公开号：US7608633B2

  公开（公告）日：2009-10-27
• Design and Synthesis of 1-Indol-1-yl-propan-2-ones as Inhibitors of Human Cytosolic Phospholipase A₂α
  作者：Joachim Ludwig、Stefanie Bovens、Carsten Brauch、Alwine Schulze Elfringhoff、Matthias Lehr

  DOI：10.1021/jm051243a

  日期：2006.4.1

  The synthesis and structure-activity relationship study of a series of 1-indol-1-yl-3-phenoxypropan-2-one inhibitors of cytosolic phospholipase A(2)alpha (cPLA(2)alpha) are described. The compounds were evaluated in a vesicle assay with isolated cPLA(2)alpha and in cellular assays with intact human platelets. Systematic variation led to 3-methylhydrogen 1-[3-(4-decyloxyphenoxy)-2-oxopropyl]indole-3,5-dicarboxylate (57), which revealed the highest activity against the isolated enzyme. With an IC50 value of 4.3 nM in this assay, it is one of the most potent in vitro cPLA(2)alpha inhibitors known today.