苄基5-甲氧基-2-甲基吲哚-3-乙酸酯 | 3285-40-3

• 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: 苄基5-甲氧基-2-甲基吲哚-3-乙酸酯
• 中文别名: 5-甲氧基-2-甲基吲哚-3-乙酸苄酯
• 英文名称: (5-methoxy-2-methyl-1H-indol-3-yl)acetic acid benzyl ester
• 英文别名: 5-methoxy-2-methyl-1H-indole-3-acetic acid benzyl ester；benzyl-(2-methyl-5-methoxy-3-indolyl)-acetate；Benzyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate
• CAS: 3285-40-3
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: CIYYFSIPIJCMHH-UHFFFAOYSA-N

物化性质

• 沸点：
  490.5±40.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  苄基5-甲氧基-2-甲基吲哚-3-乙酸酯 在 palladium on activated charcoal 氢气 作用下， 生成 1-(1-adamantoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid
  参考文献：
  名称：

  Boltze; Brendler; Jacobi, Arzneimittel-Forschung/Drug Research, 1980, vol. 30, # 8 A, p. 1314 - 1325

  摘要：

  DOI：
• 作为产物：
  描述：

  吲哚美辛 在 sodium methylate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 84.17h， 生成 苄基5-甲氧基-2-甲基吲哚-3-乙酸酯
  参考文献：
  名称：

  ortho-Carbaborane derivatives of indomethacin as cyclooxygenase (COX)-2 selective inhibitors

  摘要：

  A series of novel indomethacin analogues with carbaboranes as three-dimensional substitutes for the chlorophenyl ring have been prepared. Their cyclooxygenase (COX) inhibition and enzyme selectivity has been tested and compared to the corresponding adamantyl analogues. Surprisingly, only the ortho-carbaborane derivatives were active compounds. Preliminary biological studies gave an interesting insight into the validity of employing carbaboranes as pharmacophores. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.063

文献信息

• Esters and amides of substituted pyrrole acetic acids
  申请人：Cell Pathways, Inc.

  公开号：US05721347A1

  公开（公告）日：1998-02-24

  Esters and amides of substituted pyrrole acetic acids are useful in the treatment of colonic polyps.

  取代吡咯乙酸的酯和酰胺在治疗结肠息肉方面是有用的。
• Aromatic Enamide/Ene Metathesis toward Substituted Indoles and Its Application to the Synthesis of Indomethacins
  作者：Yayoi Kasaya、Kosuke Hoshi、Yukiyoshi Terada、Atsushi Nishida、Satoshi Shuto、Mitsuhiro Arisawa

  DOI：10.1002/ejoc.200900520

  日期：2009.9

  A steric and electronic effect on enamide/ene metathesis, a novel preparation of 2-substituted indoles and 3-substituted indoles using enamide-ene metathesis as a key reaction, and its application to the synthesis of indomethacin are described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  描述了烯酰胺/烯复分解的空间和电子效应，使用烯酰胺 - 烯复分解作为关键反应制备 2-取代吲哚和 3-取代吲哚的新方法，及其在吲哚美辛合成中的应用。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Indolylacetic acid derivatives and preparations containing same for medical treatments
  申请人：GREEN CROSS CORPORATION

  公开号：EP0144845A1

  公开（公告）日：1985-06-19

  Novel indoleacetic acid derivatives and a medical preparation containing such an indoleacetic acid derivative as a major constituent are described. These derivatives are represented by the general formula: wherein all the symbols are as defined in the appended claims. The derivatives are highly soluble in lipid and can be converted into a fat emulsion in any proportion. The medical preparation is useful as an analgesic, for example.

  本文描述了新型吲哚乙酸衍生物和一种以这种吲哚乙酸衍生物为主要成分的医用制剂。 这些衍生物由通式表示： 其中所有符号均如所附权利要求中所定义。 这些衍生物极易溶于脂质，可按任何比例转化为脂肪乳剂。 这种医用制剂可用作镇痛剂等。
• Discovery of selective indole-based prostaglandin D2 receptor antagonist
  作者：Maki Iwahashi、Atsushi Shimabukuro、Takahiro Onoda、Yoko Matsunaga、Yutaka Okada、Ryoji Matsumoto、Fumio Nambu、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2011.06.014

  日期：2011.8

  A series of N-benzoyl-2-methylindole-3-acetic acids were synthesized and biologically evaluated as prostaglandin (PG) D-2 receptor antagonists. Some of the selected compounds significantly inhibited OVA-induced vascular permeability in guinea pig conjunctiva after oral dosing. Structure-activity relationship study is presented. (C) 2011 Elsevier Ltd. All rights reserved.
• Design and Synthesis of Indomethacin Analogues That Inhibit P-Glycoprotein and/or Multidrug Resistant Protein without Cox Inhibitory Activity
  作者：Mitsuhiro Arisawa、Yayoi Kasaya、Tohru Obata、Takuma Sasaki、Tomonori Nakamura、Takuya Araki、Koujirou Yamamoto、Akito Sasaki、Akihito Yamano、Mika Ito、Hiroshi Abe、Yoshihiro Ito、Satoshi Shuto

  DOI：10.1021/jm301084z

  日期：2012.9.27

  We designed and synthesized conformationally restricted analogues and regioisomers of the nonsteroidal anti-inflammatory drug indomethacin. Evaluation of the inhibitory effects of these compounds on COX, P-glycoprotein, and multidrug resistance indicated that NSAIDS modulation of multidrug-resistant P-glycoprotein and multidrug-resistant protein-1 is not associated with COX-1 and COX-2 inhibitory activities.