methyl (2E)-3-(2-amino-5-ethylphenyl)acrylate | 231296-77-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (2E)-3-(2-amino-5-ethylphenyl)acrylate
• 英文别名: methyl trans-5-ethyl-2-aminocinnamate；methyl (E)-3-(2-amino-5-ethylphenyl)prop-2-enoate
• CAS: 231296-77-8
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: CVUHQUCSHBJJEF-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2E)-3-(2-amino-5-ethylphenyl)acrylate 生成 methyl (2E)-3-{5-ethyl-2-[(phenylsulfonyl)amino]phenyl}acrylate
  参考文献：
  名称：

  2,3-substituted indole compounds as anti-inflammatory and analgesic agents

  摘要：

  这项发明提供了以下式的化合物： 或其药学上可接受的盐，其中Z为OH、C1-6烷氧基、—NR2R3或杂环；Q从以下中选择：(a) 可选择取代的苯基，(b) 可选择取代的含有一个、两个、三个或四个氮原子的6-成员单环芳基，(c) 可选择取代的含有O、S和N中选择的一个杂原子的5-成员单环芳基，并且除所述杂原子外还可选择含有一个、两个或三个氮原子，(d) 可选择取代的C3-7环烷基和(e) 可选择取代的苯并噻吩杂环；R1为氢、C1-4烷基或卤素；R2和R3独立地为氢、OH、C1-4烷氧基、C1-4烷基或用卤素、OH、C1-4烷氧基或CN取代的C1-4烷基；X独立地从H、卤素、C1-4烷基、卤素取代的C1-4烷基、OH、C1-4烷氧基、卤素取代的C1-4烷氧基、C1-4烷基硫醚、NO2、NH2、二-(C1-4烷基)氨基和CN中选择；n为0、1、2、3和4。 这项发明还提供了一种用于治疗前列腺素参与的医疗状况的药物组合物。

  公开号：

  US06608070B1
• 作为产物：
  描述：

  N-(2-bromo-4-ethylphenyl)acetamide 在 盐酸 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 12.5h， 生成 methyl (2E)-3-(2-amino-5-ethylphenyl)acrylate
  参考文献：
  名称：

  Novel acid-type cyclooxygenase-2 inhibitors: Design, synthesis, and structure–activity relationship for anti-inflammatory drug

  摘要：

  Cyclooxygenase (COX) is a key rate-limiting enzyme for prostaglandin (PG) production cascades in the human body. The mechanisms of both the anti-inflammation effects and the side-effects of traditional COX inhibitors are associated with the existence of two COX isoforms. Thus while COX-1 is predominantly expressed ubiquitously and constitutively, and it serves a housekeeping role in processes such as gastrointestinal (GI) mucosa protection, COX-2 is absent or exhibits a low level of expression in most tissues, and is highly upregulated in response to endotoxin, virus, inflammatory or tissue-injury stimuli/signals, and tumour promoter in the various types of organs, tissues, and cells. Furthermore, COX-2 contribution to PGE(2) and PGI(2) production evokes and sustains systemic or peripheral inflammatory disease, but it is not involved in the COX-1-mediated GI tract events. Also, hypersensitivity of aspirin owing to its inhibitory action against COX-1 is a significant concern clinically. Consequently, highly selective COX-2 inhibitors have been needed for the treatment of inflammatory- and inflammation related-diseases that include pyrexia, inflammation, pain, rheumatoid arthritis, osteoarthritis, and cancers. In this study, a series of novel [2-{[(4-substituted or 4,5-disubstituted)-pyridin-2-yl]carbonyl}-(5- or 6-substituted or 5,6-disubstituted)-1H-indol-3-yl]acetic acid analogues was designed, synthesized, and evaluated to identify potent and selective COX-2 inhibitors as potential agents against inflammatory diseases. As significant findings, the present study clarified unique structure activity relationship of the analogues toward potent and selective COX-2 inhibition in vitro, and identified 2-{6-fluoro-2-[4-methyl-2-pridinyl)carbonyl]-1H-indol-3-yl}acetic acid as a potent and selective COX-2 inhibitor in vitro that demonstrated orally potent anti-inflammation efficacy against carrageenan-induced oedema formation in the foot of SPF/VAF male SD rats as a peripheral inflammation model in vivo. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.053

文献信息

• 2,3-SUBSTITUTED INDOLE COMPOUNDS AS COX-2 INHIBITORS
  申请人：PFIZER INC.

  公开号：EP1045833B1

  公开（公告）日：2005-11-02
• THIENODIBENZOAZULENE COMPOUNDS AS TUMOR NECROSIS FACTOR INHIBITORS
  申请人：Pliva, Farmaceutska, Industrija, Dionicko Drustvo

  公开号：EP1284977A1

  公开（公告）日：2003-02-26
• US6608070B1
  申请人：——

  公开号：US6608070B1

  公开（公告）日：2003-08-19
• [EN] THIENODIBENZOAZULENE COMPOUNDS AS TUMOR NECROSIS FACTOR INHIBITORS<br/>[FR] UTILISATION DE COMPOSES A BASE DE THIENODIBENZOAZULENE COMME INHIBITEURS DU FACTEUR DE NECROSE TUMORALE
  申请人：PLIVA FARMACEUTSKA IND DIONIKO

  公开号：WO2001087890A1

  公开（公告）日：2001-11-22

  The present invention relates to the dibenzoazulene compounds represented by formula I as well as to their pharmaceutical preparations for the inhibition of tumor necrosis factor alpha (TNF-α) and interleukine 1 (IL-1) in mammals at all diseases and conditions where these mediators are excessively secreted. The compounds of the present invention also demonstrate an analgetic action and can be used to relieve pain.