2-[5-甲氧基-1-(4-甲氧基苯甲酰基)-2-甲基吲哚-3-基]乙酸 | 1568-31-6

• 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-[5-甲氧基-1-(4-甲氧基苯甲酰基)-2-甲基吲哚-3-基]乙酸
• 英文名称: 2-(5-methoxy-1-(4-methoxybenzoyl)-2-methyl-1H-indol-3-yl)acetic acid
• 英文别名: 1-(4-methoxybenzoyl)-5-methoxy-2-methyl-indole-3-acetic acid；[5-methoxy-1-(4-methoxy-benzoyl)-2-methyl-indol-3-yl]-acetic acid；[5-methoxy-1-(4-methoxybenzoyl)-2-methyl-indol-3-yl]-acetic acid；1-(4-Methoxybenzoyl)-2-methyl-3-carboxymethyl-5-methoxyindol；1h-Indole-3-acetic acid,5-methoxy-1-(4-methoxybenzoyl)-2-methyl-；2-[5-methoxy-1-(4-methoxybenzoyl)-2-methylindol-3-yl]acetic acid
• CAS: 1568-31-6
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: VRBHWYPDTWECKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[5-甲氧基-1-(4-甲氧基苯甲酰基)-2-甲基吲哚-3-基]乙酸 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 生成 (3-Carboxymethyl-5-methoxy-2-methyl-indol-1-yl)-hydroxy-(4-methoxy-phenyl)-methanol anion
  参考文献：
  名称：

  吲哚美辛及相关化合物基本水解的动力学和机理：重新评估。

  摘要：

  在25度碱性介质中研究了消炎痛及其相关化合物的水解动力学。根据对数吸光度与时间图在紫外线下评估伪一级反应速率常数。这些化合物在低浓度的氢氧根离子下显示出二级速率常数，而在较高浓度的氢氧根离子下显示出一级速率常数。

  DOI：

  10.1002/jps.2600720928
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 在 吡啶 、 盐酸 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 5.67h， 生成 2-[5-甲氧基-1-(4-甲氧基苯甲酰基)-2-甲基吲哚-3-基]乙酸
  参考文献：
  名称：

  Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead

  摘要：

  A series of N-(p-alkoxy)benzoyl-5-methoxy-2-methylindole-3-acetic acids and N-(p-butoxy)benzoyl-2-methylindole-4-acetic acid were discovered as new chemical leads for a prostaglandin D-2 (PGD(2)) receptor antagonist. Most of them exhibited PGD(2) receptor binding and blocked cyclic adenosine 3',5'-monophosphate (cAMP) formation in vitro. In particular, 2-methylindole-4-acetic acid analog 1 showed markedly increased receptor affinity and cAMP antagonist activity. Chemistry and structure activity relationship (SAR) data are also presented. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.011

文献信息

• Micellar Effects on the basic Hydrolysis of Indomethacin and Related Compounds
  作者：Antonio Cipiciani、Cynthia Ebert、Raimondo Germani、Paolo Linda、Mara Lovrecich、Fulvio Rubessa、Gianfranco Savelli

  DOI：10.1002/jps.2600741110

  日期：1985.11

  The kinetics of hydrolysis of indomethacin and related compounds was studied in an alkaline medium at 25 degrees C in the presence of anionic (sodium dodecyl sulfate) and cationic (hexadecyltrimethylammonium bromide) surfactants. The rate-surfactant profiles for rate inhibition in the presence of sodium dodecyl sulfate and rate enhancement in the presence of hexadecyltrimethylammonium bromide were

  在25℃的碱性介质中，在阴离子（十二烷基硫酸钠）和阳离子（十六烷基三甲基溴化铵）表面活性剂的存在下，研究了吲哚美辛和相关化合物的水解动力学。根据胶束效应理论，分析了在十二烷基硫酸钠存在时抑制速率和在十六烷基三甲基溴化铵存在下速率提高的速率表面活性剂谱。
• 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。
• Straightforward protocol for the efficient synthesis of varied N1-acylated (aza)indole 2-/3-alkanoic acids and esters: optimization and scale-up
  作者：Andy J. Liedtke、Kwangho Kim、Donald F. Stec、Gary A. Sulikowski、Lawrence J. Marnett

  DOI：10.1016/j.tet.2012.08.044

  日期：2012.12

  A library of approximately 40 N-1-acylated (aza)indole alkanoic esters and acids was prepared employing a microwave-assisted approach. The optimized synthetic route allows for parallel synthesis, variation of the indole substitution pattern, and high overall yield. Additionally, the procedure has been scaled up to yield multi-gram amounts of preferred indole compounds, e.g.: 2'-des-methyl indomethacin 2. The reported compounds were designed as biomedical tools for primary and secondary in vitro and in vivo studies at relevant molecular targets. (C) 2012 Elsevier Ltd. All rights reserved.
• MIHALIC M.; SUNJIC V.; KAJFEZ F.; CAPLAR V.; KOVAC T., CROAT. CHEM. ACTA, 1978, 51, NO 1, 81-92
  作者：MIHALIC M.、 SUNJIC V.、 KAJFEZ F.、 CAPLAR V.、 KOVAC T.

  DOI：——

  日期：——
• NOVEL INDOLE DERIVATIVES USEFUL TO TREAT ESTROGEN-RELATED NEOPLASMS AND DISORDERS
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0746544A1

  公开（公告）日：1996-12-11