(2R)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoic acid | 1469996-63-1

• 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: (2R)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoic acid
• CAS: 1469996-63-1
• 化学式: C₂₃H₂₀ClNO₄
• 分子量: 409.869
• InChiKey: GYSBWGOUYCPZIK-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoic acid 、 对氯苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 以14%的产率得到2-(benzyloxy)-5-chloro-N-[(2R)-1-[(4-chlorophenyl)amino]-1-oxo-3-phenylpropan-2-yl]benzamide
  参考文献：
  名称：

  Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines

  摘要：

  Variously substituted 2-hydroxy-N-(arylallcyl)benzamides were prepared and screened for anti-proliferative and cytotoxic activity in cancer cell lines in vitro. Five compounds, out of 33 showed single-digit micromolar IC50 values against several human cancer cell lines. One of the most potent compounds N-((R)-1-(4-chlorophenylcarbamoyl)-2-phenylethyl)-5-chloro-2-hydroxybenzamide (6k) reduced proliferation and induced apoptosis in the melanoma cell line G361 in a dose-dependent manner, as shown by decrease in 5-bromo-2'-deoxyuridine incorporation and increase in several apoptotic markers, including subdiploid population increase, activation of caspases and site-specific poly-(ADP-ribose)polymerase (PARP) cleavage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.009
• 作为产物：
  描述：

  methyl (2R)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoate 在 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以73%的产率得到(2R)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines

  摘要：

  Variously substituted 2-hydroxy-N-(arylallcyl)benzamides were prepared and screened for anti-proliferative and cytotoxic activity in cancer cell lines in vitro. Five compounds, out of 33 showed single-digit micromolar IC50 values against several human cancer cell lines. One of the most potent compounds N-((R)-1-(4-chlorophenylcarbamoyl)-2-phenylethyl)-5-chloro-2-hydroxybenzamide (6k) reduced proliferation and induced apoptosis in the melanoma cell line G361 in a dose-dependent manner, as shown by decrease in 5-bromo-2'-deoxyuridine incorporation and increase in several apoptotic markers, including subdiploid population increase, activation of caspases and site-specific poly-(ADP-ribose)polymerase (PARP) cleavage. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.009