2-((1-carboxy-2-phenylethyl)carbamoyl)benzoic acid | 34564-00-6

• 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-carboxy-2-phenylethyl)carbamoyl)benzoic acid
• 英文别名: (+/-)-N-(2-Carboxy-benzoyl)-phenylalanin；DL-N-(o-Carboxybenzoyl)-phenylalanin；N-Phthalyl-DL-β-phenylalanine；N-(2-Carboxybenzoyl)-D-phenylalanine；2-[(1-carboxy-2-phenylethyl)carbamoyl]benzoic acid
• CAS: 34564-00-6
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: WMYRYTHPUNNJQO-UHFFFAOYSA-N

物化性质

• 沸点：
  605.6±55.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((1-carboxy-2-phenylethyl)carbamoyl)benzoic acid 在 草酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-((1-(benzyl(2-hydroxy-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
• 作为产物：
  描述：

  DL-苯基丙氨酸甲酯盐酸盐 在 水 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 2-((1-carboxy-2-phenylethyl)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

文献信息

• COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS
  申请人：THE CALIFORNIA INSTITUTE FOR BIOMEDICAL RESEARCH

  公开号：US20160045514A1

  公开（公告）日：2016-02-18

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

  本文描述了一种化合物和组合物，通过将间充质干细胞诱导为软骨细胞，用于改善关节炎或关节损伤的方法。
• Compounds and methods for inducing chondrogenesis
  申请人：The Scripps Research Institute

  公开号：US11045476B2

  公开（公告）日：2021-06-29

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.

  本文描述了通过诱导间充质干细胞转化为软骨细胞来改善关节炎或关节损伤的化合物和组合物。
• US20140271955A1
  申请人：——

  公开号：US20140271955A1

  公开（公告）日：2014-09-18
• US9452170B2
  申请人：——

  公开号：US9452170B2

  公开（公告）日：2016-09-27
• [EN] COMPOUNDS AND METHODS FOR INDUCING CHONDROGENESIS<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR L'INDUCTION DE LA CHONDROGENÈSE
  申请人：CALIFORNIA INST BIOMEDICAL RES

  公开号：WO2014151953A1

  公开（公告）日：2014-09-25

  Described herein are compounds and compositions for the amelioration of arthritis or joint injuries by inducing mesenchymal stem cells into chondrocytes.