2-(1-苄基-5-甲氧基-2-甲基吲哚-3-基)乙酸 | 59283-35-1

• 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: 2-(1-苄基-5-甲氧基-2-甲基吲哚-3-基)乙酸
• 英文名称: 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indol-3-ylacetic acid
• 英文别名: 1-benzyl-5-methoxy-2-methylindole-3-acetic acid；(1-benzyl-5-methoxy-2-methyl-indol-3-yl)-acetic acid；(1-Benzyl-5-methoxy-2-methyl-indol-3-yl)-essigsaeure；5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid；1-[5-methoxy-1-benzyl-2-methyl-1H-indol-3-yl]-acetic acid；<1-Benzyl-5-methoxy-2-methyl-indolyl-(3)>-essigsaeure；1-Benzyl-5-methoxy-2-methyl-1h-indol-3-yl)-acetic acid；2-(1-benzyl-5-methoxy-2-methylindol-3-yl)acetic acid
• CAS: 59283-35-1
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: ZEKCBTQHDTUHRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-苄基-5-甲氧基-2-甲基吲哚-3-基)乙酸 在 甲醇 、 甲烷磺酸 、 三溴化硼 作用下， 反应 23.5h， 生成 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester
  参考文献：
  名称：

  Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 2. Indole-3-acetamides with Additional Functionality

  摘要：

  As reported in our previous paper, a series of indole-3-acetamides which possessed potency and selectivity as inhibitors of human nonpancreatic secretory phospholipase A(2)(hnps-PLA(2)) was developed. The design of these compounds was based on information derived from x-ray crystal structures determined for complexes between the enzyme and its inhibitors. We describe here the further implementation of this structure-based design strategy and continued SAR development to produce indole-3-acetamides with additional functionalities which provide increased interaction with important residues within the enzyme active site. These efforts led to inhibitors with substantially enhanced potency and selectivity.

  DOI：

  10.1021/jm960486n
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 在 sodium hydroxide 、 溶剂黄146 作用下， 生成 2-(1-苄基-5-甲氧基-2-甲基吲哚-3-基)乙酸
  参考文献：
  名称：

  The Synthesis of Tryptamines Related to Serotonin

  摘要：

  DOI：

  10.1021/ja01621a042

文献信息

• 1H-indole-3-acetamide sPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US05684034A1

  公开（公告）日：1997-11-04

  A class of novel 1-indole-3-acetamides represented by the formula; ##STR1## is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids.

  一类由以下式表示的新型1-吲哚-3-乙酰胺类化合物被揭示，同时还公开了利用这类吲哚化合物抑制sPLA.sub.2介导的脂肪酸释放的用途。
• Multivalent indole compounds and use thereof as phospholipase-A2 inhibitors
  申请人：Chang Han-Ting

  公开号：US20070135385A1

  公开（公告）日：2007-06-14

  Indole and indole-related compounds, compositions and methods are disclosed. The compounds of the invention are useful as phospholipase inhibitors. The compounds and compositions of the invention are useful for treatment of phospholipase-related conditions, such as insulin-related, weight-related and/or cholesterol-related conditions in an animal subject.

  吲哚和与吲哚相关的化合物、组合物以及方法被披露。发明中的这些化合物作为磷脂酶抑制剂非常有用。发明中的这些化合物和组合物用于治疗动物受试者中的磷脂酶相关状况，例如胰岛素相关、体重相关和/或胆固醇相关状况。
• 1H-indole-3-acetic acid hydrazide sPLA.sub.2 inhibitors
  申请人：Eli Lilly and Company

  公开号：US05578634A1

  公开（公告）日：1996-11-26

  A class of novel 1H-indole-3-acetic acid hydrazides is disclosed together with the use of such indole compounds for inhibiting sPLA.sub.2 mediated release of fatty acids (e.g., arachidonic acid) for treatment of conditions such as septic shock.

  一类新型的1H-吲哚-3-乙酸肼类化合物被揭示，以及利用这类吲哚化合物抑制sPLA.sub.2介导的脂肪酸（例如花生四烯酸）释放，用于治疗诸如感染性休克等疾病。
• Indole Inhibitors of Human Nonpancreatic Secretory Phospholipase A₂. 1. Indole-3-acetamides
  作者：Robert D. Dillard、Nicholas J. Bach、Susan E. Draheim、Dennis R. Berry、Donald G. Carlson、Nickolay Y. Chirgadze、David K. Clawson、Lawrence W. Hartley、Lea M. Johnson、Noel D. Jones、Emma R. McKinney、Edward D. Mihelich、Jennifer L. Olkowski、Richard W. Schevitz、Amy C. Smith、David W. Snyder、Cynthia D. Sommers、Jean-Pierre Wery

  DOI：10.1021/jm960485v

  日期：1996.1.1

  Phospholipases (PLAs) produce rate-limiting precursors in the biosynthesis of various types of biologically active lipids involved in inflammatory processes. Increased levels of human nonpancreatic secretory phospholipase A2 (hnps-PLA2) have been detected in several pathological conditions. An inhibitor of this enzyme could have therapeutic utility. A broad screening program was carried out to identify

  磷脂酶（PLA）在涉及炎症过程的各种类型生物活性脂质的生物合成中产生限速前体。在几种病理条件下已检测到人类非胰腺分泌型磷脂酶A2（hnps-PLA2）水平升高。该酶的抑制剂可以具有治疗用途。进行了广泛的筛选程序以鉴定可能抑制hnps-PLA2的化学结构。通过筛选程序生成的先导化合物之一是5-甲氧基-2-甲基-1-（苯甲基）-1H-吲哚-3-乙酸（13a）。我们描述了一系列吲哚-3-乙酰胺及其衍生化合物的合成，结构-活性关系以及药理活性。
• Indole derivatives useful to treat estrogen-related neoplasms and
  申请人：——

  公开号：US05877202A1

  公开（公告）日：1999-03-02

  The present invention relates to novel indole derivatives useful in down-regulating estrogen receptor expression. Also included are methods for the treatment of neoplasms or of controlling the growth of a neoplasm in a patient afflicted with a neoplastic disease, especially estrogen-dependent neoplasms such as those associated with breast, ovarian and cervical tissue. Another embodiment of the present invention is a method of prophylactically treating a patient at risk of developing a neoplastic disease state. Also provided is a method for treating autoimmune diseases. Also included are pharmaceutical compositions of the novel indole derivatives.

  本发明涉及一种新型吲哚衍生物，可用于下调雌激素受体表达。还包括用于治疗肿瘤或控制患有肿瘤疾病的患者中的肿瘤生长的方法，特别是与乳腺、卵巢和宫颈组织相关的雌激素依赖性肿瘤。本发明的另一实施例是一种预防性治疗患有发展肿瘤疾病风险的患者的方法。还提供了一种用于治疗自身免疫疾病的方法。还包括新型吲哚衍生物的药物组合物。