N-(but-3-yn-1-yl)-3,5-bis(trifluoromethyl)benzamide | 1207114-07-5

• 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: N-(but-3-yn-1-yl)-3,5-bis(trifluoromethyl)benzamide
• 英文别名: N-but-3-ynyl-3,5-bis(trifluoromethyl)benzamide
• CAS: 1207114-07-5
• 化学式: C₁₃H₉F₆NO
• 分子量: 309.211
• InChiKey: GAQRBBRANVUMQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-叠氮-4-氯苯 、 N-(but-3-yn-1-yl)-3,5-bis(trifluoromethyl)benzamide 在 copper(II) sulfate 、 维生素 C 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.0h， 以10%的产率得到N-[2-[1-(4-chlorophenyl)triazol-4-yl]ethyl]-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

  摘要：

  We recently identified bis(amide) CCG-1423 (1) as a novel inhibitor of RhoA/C-mediated gene transcription that is capable of inhibiting invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis. An initial structure-activity relationship study focusing on bioisosteric replacement of the amides and conformational restriction identified two compounds, 4g and 8, with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxicity relative to 1. Both compounds were also capable of inhibiting cell invasion with equal efficacy to 1 but with less attendant cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.056
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲酰氯 、 3-丁炔-1-胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到N-(but-3-yn-1-yl)-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and prostate cancer cell-based studies of analogs of the Rho/MKL1 transcriptional pathway inhibitor, CCG-1423

  摘要：

  We recently identified bis(amide) CCG-1423 (1) as a novel inhibitor of RhoA/C-mediated gene transcription that is capable of inhibiting invasion of PC-3 prostate cancer cells in a Matrigel model of metastasis. An initial structure-activity relationship study focusing on bioisosteric replacement of the amides and conformational restriction identified two compounds, 4g and 8, with improved selectivity for inhibition of RhoA/C-mediated gene transcription and attenuated cytotoxicity relative to 1. Both compounds were also capable of inhibiting cell invasion with equal efficacy to 1 but with less attendant cytotoxicity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.056