(2S)-2-[[2-(benzyloxy)-4-chlorobenzoyl]amino]propanoic acid | 1469996-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[[2-(benzyloxy)-4-chlorobenzoyl]amino]propanoic acid
• CAS: 1469996-66-4
• 化学式: C₁₇H₁₆ClNO₄
• 分子量: 333.771
• InChiKey: QUPUQOKIFYPRKO-NSHDSACASA-N

物化性质

• 熔点：
  169-172 °C
• 沸点：
  538.7±50.0 °C(predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  (2S)-2-[[2-(benzyloxy)-4-chlorobenzoyl]amino]propanoic acid 、 3,4-二氯苯胺 在 palladium 10% on activated carbon 、 氢气 、 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 、 乙酸乙酯 为溶剂， 5.0~20.0 ℃ 、101.33 kPa 条件下， 反应 28.5h， 生成 4-chloro-2-hydroxy-N-[(2S)-1-[(3,4-dichlorophenyl)amino]-1-oxopropan-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 (2S)-2-[[2-(benzyloxy)-4-chlorobenzoyl]amino]propanoate 在 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.75h， 以79%的产率得到(2S)-2-[[2-(benzyloxy)-4-chlorobenzoyl]amino]propanoic 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