methyl 2-[4-(5-((E)-1-propenyl)-pyridin-3-yl)phenyl]propanoate | 236747-78-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: methyl 2-[4-(5-((E)-1-propenyl)-pyridin-3-yl)phenyl]propanoate
• 英文别名: methyl 2-[4-(5-((E)-1-propenyl)-3-pyridyl)phenyl]propanoate；methyl 2-[4-[5-[(E)-prop-1-enyl]pyridin-3-yl]phenyl]propanoate
• CAS: 236747-78-7
• 化学式: C₁₈H₁₉NO₂
• 分子量: 281.354
• InChiKey: DVYKCRZUHFWRHB-SNAWJCMRSA-N

物化性质

• 沸点：
  418.788±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.086±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-(5-((E)-1-propenyl)-pyridin-3-yl)phenyl]propanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2-[4-(5-((E)-1-Propenyl)-pyridin-3-yl)phenyl]propanoic acid
  参考文献：
  名称：

  Bisaryl COX-2 inhibiting compounds, compositions and methods of use

  摘要：

  这项发明涉及COX-2的抑制剂，包含这类化合物的组合物以及使用方法。这些化合物由式I代表：##STR1##，并包括其药用可接受的盐和酯。

  公开号：

  US05994379A1
• 作为产物：
  描述：

  2-(4-溴苯基)丙酸甲酯 、 3-Bromo-5-((E)-propenyl)-pyridine 在 正丁基锂 、 tris(dibenzylideneacetone)dipalladium (0) 、 硼酸三异丙酯 、 sodium carbonate 、 三苯基膦 作用下， 生成 methyl 2-[4-(5-((E)-1-propenyl)-pyridin-3-yl)phenyl]propanoate
  参考文献：
  名称：

  Structure-based design of COX-2 selectivity into flurbiprofen

  摘要：

  Comparative computer modeling of the X-ray crystal structures of cyclooxygenase isoforms COX-1 and COX-2 has led to the design of COX-2 selectivity into the nonselective inhibitor flurbiprofen. The COX-2 modeling was based on a postulated binding mode for flurbiprofen and took advantage of a small alcove in the COX-2 active site created by different positions of the Leu384 sidechain between COX-I and COX-2. The design hypothesis was tested by synthesis and biological assay of a series of flurbiprofen analogs, culminating in the discovery of several inhibitors having up to 78-fold selectivity for COX-2 over COX-1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00717-3

文献信息

• BIARYL-ACETIC ACID DERIVATIVES AND THEIR USE AS COX-2 INHIBITORS
  申请人：Merck Frosst Canada & Co.

  公开号：EP1054857B1

  公开（公告）日：2003-11-05
• US5994379A
  申请人：——

  公开号：US5994379A

  公开（公告）日：1999-11-30
• Bisaryl COX-2 inhibiting compounds, compositions and methods of use
  申请人：Merck Frosst Canada, Inc.

  公开号：US05994379A1

  公开（公告）日：1999-11-30

  The present invention relates to inhibitors of COX-2, compositions which contain such compounds and methods of use. The compounds are represented by formula I: ##STR1## and include pharmaceutically acceptable salts and esters thereof.

  这项发明涉及COX-2的抑制剂，包含这类化合物的组合物以及使用方法。这些化合物由式I代表：##STR1##，并包括其药用可接受的盐和酯。
• Structure-based design of COX-2 selectivity into flurbiprofen
  作者：Christopher I. Bayly、W.Cameron Black、Serge Léger、Nathalie Ouimet、Marc Ouellet、M.David Percival

  DOI：10.1016/s0960-894x(98)00717-3

  日期：1999.2

  Comparative computer modeling of the X-ray crystal structures of cyclooxygenase isoforms COX-1 and COX-2 has led to the design of COX-2 selectivity into the nonselective inhibitor flurbiprofen. The COX-2 modeling was based on a postulated binding mode for flurbiprofen and took advantage of a small alcove in the COX-2 active site created by different positions of the Leu384 sidechain between COX-I and COX-2. The design hypothesis was tested by synthesis and biological assay of a series of flurbiprofen analogs, culminating in the discovery of several inhibitors having up to 78-fold selectivity for COX-2 over COX-1. (C) 1999 Elsevier Science Ltd. All rights reserved.