2-(2-methylbenzofuran-3-yl)ethanamine | 910395-51-6

• 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: 2-(2-methylbenzofuran-3-yl)ethanamine
• 英文别名: 2-(2-methylbenzofuran-3-yl)ethan-1-amine；2-(2-Methyl-1-benzofuran-3-yl)ethan-1-amine；2-(2-methyl-1-benzofuran-3-yl)ethanamine
• CAS: 910395-51-6
• 化学式: C₁₁H₁₃NO
• mdl: MFCD08449800
• 分子量: 175.23
• InChiKey: FPHABPQYVPYGBL-UHFFFAOYSA-N

物化性质

• 沸点：
  292.4±25.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  39.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4,5-三甲氧基肉桂酸 、 2-(2-methylbenzofuran-3-yl)ethanamine 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以65%的产率得到(E)-N-(2-(2-methylbenzofuran-3-yl)ethyl)-3-(3,4,5-trimethoxyphenyl)acrylamide
  参考文献：
  名称：

  Lead Optimization Studies of Cinnamic Amide EP2 Antagonists

  摘要：

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.

  DOI：

  10.1021/jm5000672
• 作为产物：
  描述：

  2-(2-methylbenzofuran-3-yl)acetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-methylbenzofuran-3-yl)ethanamine
  参考文献：
  名称：

  Lead Optimization Studies of Cinnamic Amide EP2 Antagonists

  摘要：

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.

  DOI：

  10.1021/jm5000672

文献信息

• [EN] BENZOFURANE AND BENZOTHIOPHENE DERIVATIVES AS PGE2 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE BENZOFURANE ET DE BENZOTHIOPHÈNE UTILISÉS EN TANT QUE MODULATEURS DU RÉCEPTEUR PGE2
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：WO2018210987A1

  公开（公告）日：2018-11-22

  The present invention relates to benzofurane and benzothiophene derivatives of formula (I) Formula (I) wherein (R1)n, R2, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及公式(I)的苯并呋喃和苯并噻吩衍生物，其中(R1)n，R2，R3，R4a，R4b，R5a，R5b和Ar1如描述中所述，并且它们在通过调节免疫应答包括在肿瘤中重新激活免疫系统的治疗中的用途。该发明还涉及公式(II)的新型苯并呋喃和苯并噻吩衍生物及其作为药物的用途，其制备，其药学上可接受的盐，以及其作为药物的用途，含有一个或多个公式(I)化合物的药物组合物，特别是它们作为前列腺素2受体EP2和/或EP4的调节剂的用途。
• Benzofurane and benzothiophene derivatives as PGE2 receptor modulators
  申请人：IDORSIA PHARMACEUTICALS LTD

  公开号：US11325899B2

  公开（公告）日：2022-05-10

  The present invention relates to benzofurane and benzothiophene derivatives of formula (I) wherein (R1)n, R2, R3, R4a, R4b, R5a, R5b and Ar1 are as described in the description and their use in the treatment of cancer by modulating an immune response comprising a reactivation of the immune system in the tumor. The invention further relates to novel benzofurane and benzothiophene derivatives of formula (II) and their use as pharmaceuticals, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), and especially to their use as modulators of the prostaglandin 2 receptors EP2 and/or EP4.

  本发明涉及式 (I) 的苯并呋喃和苯并噻吩衍生物 其中(R1)n、R2、R3、R4a、R4b、R5a、R5b 和 Ar1 如说明书所述，以及它们通过调节免疫反应（包括重新激活肿瘤中的免疫系统）治疗癌症的用途。本发明进一步涉及式(II)的新型苯并呋喃和苯并噻吩衍生物及其作为药物的用途、它们的制备、它们的药学上可接受的盐及其作为药物的用途、含有一种或多种式(I)化合物的药物组合物，特别是它们作为前列腺素2受体EP2和/或EP4的调节剂的用途。
• BENZOFURANE AND BENZOTHIOPHENE DERIVATIVES AS PGE2 RECEPTOR MODULATORS
  申请人：Idorsia Pharmaceuticals Ltd

  公开号：EP3625227A1

  公开（公告）日：2020-03-25
• Lead Optimization Studies of Cinnamic Amide EP2 Antagonists
  作者：Thota Ganesh、Jianxiong Jiang、Myung-Soon Yang、Ray Dingledine

  DOI：10.1021/jm5000672

  日期：2014.5.22

  Prostanoid receptor EP2 can play a proinflammatory role, exacerbating disease pathology in a variety of central nervous system and peripheral diseases. A highly selective EP2 antagonist could be useful as a drug to mitigate the inflammatory consequences of EP2 activation. We recently identified a cinnamic amide class of EP2 antagonists. The lead compound in this class (5d) displays anti-inflammatory and neuroprotective actions. However, this compound exhibited moderate selectivity to EP2 over the DP1 prostanoid receptor (similar to 10-fold) and low aqueous solubility. We now report compounds that display up to 180-fold selectivity against DP1 and up to 9-fold higher aqueous solubility than our previous lead. The newly developed compounds also display higher selectivity against EP4 and IP receptors and a comparable plasma pharmacokinetics. Thus, these compounds are useful for proof of concept studies in a variety of models where EP2 activation is playing a deleterious role.