5-chloro-2-hydroxy-N-[(2S)-1-oxo-1-[[4-(trifluoromethyl)phenyl]amino]propan-2-yl]benzamide | 1469996-80-2

• 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: 5-chloro-2-hydroxy-N-[(2S)-1-oxo-1-[[4-(trifluoromethyl)phenyl]amino]propan-2-yl]benzamide
• 英文别名: 5-chloro-2-hydroxy-N-[(2S)-1-oxo-1-[4-(trifluoromethyl)anilino]propan-2-yl]benzamide
• CAS: 1469996-80-2
• 化学式: C₁₇H₁₄ClF₃N₂O₃
• 分子量: 386.758
• InChiKey: PCGZPJPOAHRBSZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl (2S)-2-[[2-(benzyloxy)-5-chlorobenzoyl]amino]propanoate 在 lithium hydroxide monohydrate 、 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 1,4-二氧六环 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 5.0~50.0 ℃ 、101.33 kPa 条件下， 反应 29.25h， 生成 5-chloro-2-hydroxy-N-[(2S)-1-oxo-1-[[4-(trifluoromethyl)phenyl]amino]propan-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

文献信息

• Substituted 2-hydroxy-N-(arylalkyl)benzamides induce apoptosis in cancer cell lines
  作者：Aleš Imramovský、Radek Jorda、Karel Pauk、Eva Řezníčková、Jan Dušek、Jiří Hanusek、Vladimír Kryštof

  DOI：10.1016/j.ejmech.2013.08.009

  日期：2013.10

  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.