3-methyl-4-propoxybenzofuran-2-carboxylic acid | 857080-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-methyl-4-propoxybenzofuran-2-carboxylic acid
• 英文别名: 4-propoxy-3-methyl-benzofuran-2-carboxylic acid；3-methyl-4-propoxy-1-benzofuran-2-carboxylic acid
• CAS: 857080-73-0
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: MQOLSTSPCSAVQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-4-propoxybenzofuran-2-carboxylic acid 、 (S)-2-(4'-aminobiphenyl-4-sulfonylamino)-3-methylbutyric acid methyl ester 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以57%的产率得到(S)-2-{4'-[(3-methyl-4-propoxy-benzofuran-2-carbonyl)-amino]-biphenyl-4-sulfonylamino}-3-methyl-butyric acid methyl ester
  参考文献：
  名称：

  Biaryl sulfonamides and methods for using same

  摘要：

  本发明涉及联苯磺酰胺及其用途，例如作为金属蛋白酶抑制剂。

  公开号：

  US20050143422A1
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 乙醇 、 sodium 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.0h， 生成 3-methyl-4-propoxybenzofuran-2-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of benzofuran derivatives as ET receptor antagonists

  摘要：

  A series of novel benzofuran carboxylic acid derivatives have been designed and synthesized, with their antagonism effect screened on ET-1-induced contraction in the rat thoracic aortic ring. Some target compounds demonstrated significant inhibitory activity, especially benzo[c]thiadiazole and benzo[c]oxadiazole compounds 29 and 30 showed potent inhibition percentage higher than the contrast compound BQ123. Further affinity and selectivity for ET binding assay showed that 29 demonstrated a dual ETA/ETB antagonism activity in nanomole level. Moreover, 30 was effective in relieving hypoxia-induced pulmonary arterial hypertension.

  DOI：

  10.1007/s00044-013-0542-3

文献信息

• [EN] BIARYL SULFONAMIDES AS MMP INHIBITORS<br/>[FR] SULFONAMIDES BIARYLIQUES INHIBITEURS DE MMP
  申请人：WYETH CORP

  公开号：WO2005061477A1

  公开（公告）日：2005-07-07

  The present invention relates to biaryl sulfonamides and their use as, for example, metalloproteinase inhibitors: Formule (I).

  本发明涉及联苯磺酰胺及其用途，例如，作为金属蛋白酶抑制剂：式（I）。
• Biaryl Sulfonamides and Methods for Using Same
  申请人：Levin Jeremy Ian

  公开号：US20100137298A1

  公开（公告）日：2010-06-03

  The present invention relates to biaryl sulfonamides and their use as, for example, metalloproteinase inhibitors.

  本发明涉及双芳基磺酰胺及其用途，例如作为金属蛋白酶抑制剂。
• BIARYL SULFONAMIDES AS MMP INHIBITORS
  申请人：Wyeth

  公开号：EP1692124A1

  公开（公告）日：2006-08-23
• US7420001B2
  申请人：——

  公开号：US7420001B2

  公开（公告）日：2008-09-02
• Design, synthesis, and biological evaluation of benzofuran derivatives as ET receptor antagonists
  作者：Jin Cai、Junqing Chen、Meng Cao、Peng Wang、Chengliang Feng、Min Ji

  DOI：10.1007/s00044-013-0542-3

  日期：2013.11

  A series of novel benzofuran carboxylic acid derivatives have been designed and synthesized, with their antagonism effect screened on ET-1-induced contraction in the rat thoracic aortic ring. Some target compounds demonstrated significant inhibitory activity, especially benzo[c]thiadiazole and benzo[c]oxadiazole compounds 29 and 30 showed potent inhibition percentage higher than the contrast compound BQ123. Further affinity and selectivity for ET binding assay showed that 29 demonstrated a dual ETA/ETB antagonism activity in nanomole level. Moreover, 30 was effective in relieving hypoxia-induced pulmonary arterial hypertension.