2-[[1-[[2-(4-Methylphenyl)sulfonyloxy-2-phenylethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]benzoic acid | 1402135-49-2

• 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: 2-[[1-[[2-(4-Methylphenyl)sulfonyloxy-2-phenylethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]benzoic acid
• 英文别名: 2-[[1-[[2-(4-methylphenyl)sulfonyloxy-2-phenylethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]benzoic acid
• CAS: 1402135-49-2
• 化学式: C₃₂H₃₀N₂O₇S
• 分子量: 586.665
• InChiKey: OBBWQFFMVDOYBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  DL-苯基丙氨酸甲酯盐酸盐 在 草酰氯 、 palladium 10% on activated carbon 、 水 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、4.0 MPa 条件下， 反应 26.5h， 生成 2-[[1-[[2-(4-Methylphenyl)sulfonyloxy-2-phenylethyl]amino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]benzoic acid
  参考文献：
  名称：

  Identification of Novel 2-((1-(Benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamoyl)benzoic Acid Analogues as BMP-2 Stimulators

  摘要：

  The synthesis and SAR studies of 10 new chemical entities (NCEs) that have shown BMP-2 stimulation and osteoblast differentiation are reported. Among these, 2-((1-(benzyl(2-hydroxy-2-phenylethyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamoyl)benzoic acid (11) was the most effective while its analogue 13 also showed good activity in inducing osteoblast BMP-2 production. Compound 11 induced osteoblast differentiation in vitro, and this effect was abrogated by a physiological BMP-2 inhibitor, noggin. It also exhibited dose dependent increase in nascent bone formation (2.16- and 3.12-fold more than the control at 1 and 5 mg/kg dose, respectively) at the fracture site in rats. At the maximum osteogenic concentration, compound 11 significantly inhibited osteoblastic proteosomal activity. This compound was safe, as it had no effect on BMP synthesis in cardiovascular tissue.

  DOI：

  10.1021/jm300985d