(S)-4-nitrophenyl 2-(3-benzoylphenyl)propylcarbamate | 1207759-29-2

• 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: (S)-4-nitrophenyl 2-(3-benzoylphenyl)propylcarbamate
• CAS: 1207759-29-2
• 化学式: C₂₃H₂₀N₂O₅
• 分子量: 404.422
• InChiKey: IVBUUDNWYMIIOW-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98.54
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  对羟基苯乙胺 、 (S)-4-nitrophenyl 2-(3-benzoylphenyl)propylcarbamate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 (S)-1-(2-(3-benzoylphenyl)propyl)-3-(4-hydroxyphenethyl)urea
  参考文献：
  名称：

  Structure−Activity Relationships and Cancer-Cell Selective Toxicity of Novel Inhibitors of Glioma-Associated Oncogene Homologue 1 (Gli1) Mediated Transcription

  摘要：

  We report novel inhibitors of Gli1-mediated transcription as potential anticancer agents. Focused chemical libraries were designed and assessed for inhibition of functional cell-based Gli1-mediated transcription and selective toxicity toward cancer cells. The SAR was revealed, and the selectivity of the lead compounds' inhibition of Gli1-mediated transcription over that of Gli2 was determined. Compound 63 (NMDA298-1), which inhibited Gli1-mediated transcription in C3H10T1/2 cells with all IC50 of 6.9 mu M, showed 3-fold selectivity for inhibiting transcription mediated by Gli1 over that by Gli2. Cell-viability assays were performed to evaluate the chemical library in a normal cell line and a panel of cancer cell lines with or without up-regulated expression of the Gli1 gene. These compounds decreased the viability of several cancer cell lines but were less active in the noncancerous BJ-hTERT cells.

  DOI：

  10.1021/jm900106f
• 作为产物：
  描述：

  (S)-(3-(1-aminopropan-2-yl)phenyl)(phenyl)methanone 、 对硝基苯基氯甲酸酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以72.6%的产率得到(S)-4-nitrophenyl 2-(3-benzoylphenyl)propylcarbamate
  参考文献：
  名称：

  Structure−Activity Relationships and Cancer-Cell Selective Toxicity of Novel Inhibitors of Glioma-Associated Oncogene Homologue 1 (Gli1) Mediated Transcription

  摘要：

  We report novel inhibitors of Gli1-mediated transcription as potential anticancer agents. Focused chemical libraries were designed and assessed for inhibition of functional cell-based Gli1-mediated transcription and selective toxicity toward cancer cells. The SAR was revealed, and the selectivity of the lead compounds' inhibition of Gli1-mediated transcription over that of Gli2 was determined. Compound 63 (NMDA298-1), which inhibited Gli1-mediated transcription in C3H10T1/2 cells with all IC50 of 6.9 mu M, showed 3-fold selectivity for inhibiting transcription mediated by Gli1 over that by Gli2. Cell-viability assays were performed to evaluate the chemical library in a normal cell line and a panel of cancer cell lines with or without up-regulated expression of the Gli1 gene. These compounds decreased the viability of several cancer cell lines but were less active in the noncancerous BJ-hTERT cells.

  DOI：

  10.1021/jm900106f