3-amino-3-(3,4-methylenedioxyphenyl)-1-propanoic acid methyl ester HCl salt | 1177093-05-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-amino-3-(3,4-methylenedioxyphenyl)-1-propanoic acid methyl ester HCl salt
• 英文别名: Methyl 3-amino-3-(1,3-benzodioxol-5-yl)propanoate hydrochloride；methyl 3-amino-3-(1,3-benzodioxol-5-yl)propanoate;hydrochloride
• CAS: 1177093-05-8
• 化学式: C₁₁H₁₃NO₄*ClH
• 分子量: 259.689
• InChiKey: IVKKOAMWYVPZCG-UHFFFAOYSA-N

物化性质

• 熔点：
  175～177℃

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  70.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid dihydrochloride 、 3-amino-3-(3,4-methylenedioxyphenyl)-1-propanoic acid methyl ester HCl salt 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以39%的产率得到(RS)-methyl 3-(benzo[d][1,3]dioxol-4-yl)-3-(5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanamido)propanoate
  参考文献：
  名称：

  Structure Activity Relationships of α_v Integrin Antagonists for Pulmonary Fibrosis by Variation in Aryl Substituents

  摘要：

  Antagonism of alpha(v)beta(6) is emerging as a potential treatment of idiopathic pulmonary fibrosis based on strong target validation. Starting from an alpha(v)beta(3) antagonist lead and through simple variation in the nature and position of the aryl substituent, the discovery of compounds with improved alpha(v)beta(6) activity is described. The compounds also have physicochemical properties commensurate with oral bioavailability and are high quality starting points for a drug discovery program. Compounds 33S and 43E1 are pan av antagonists having ca. 100 nM potency against alpha(v)beta(3), alpha(v)beta(5), alpha(v)beta(6), and av beta 8 in cell adhesion assays. Detailed structure activity relationships with these integrins are described which also reveal substituents providing partial selectivity (defined as at least a 0.7 log difference in pIC(50) values between the integrins in question) for alpha(v)beta(3) and alpha(v)beta(5).

  DOI：

  10.1021/ml5002079