N-[2-(4-cyanophenyl)-4-oxochromen-5-yl]-2,2-dimethylpropanamide | 179911-51-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: N-[2-(4-cyanophenyl)-4-oxochromen-5-yl]-2,2-dimethylpropanamide
• CAS: 179911-51-4
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: RGHSYJHDBNSJRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[2-(4-cyanophenyl)-4-oxochromen-5-yl]-2,2-dimethylpropanamide 在 盐酸 、 硫酸 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 21.0h， 生成 4-(5-Amino-4-oxochromen-2-yl)benzoic acid
  参考文献：
  名称：

  Novel 5-Aminoflavone Derivatives as Specific Antitumor Agents in Breast Cancer

  摘要：

  In the course of our search for new antitumor agents in breast cancer, novel amino-substituted flavone derivatives were synthesized and examined for antitumor activities. Among them, 5,4'-diaminoflavone and some of its congeners showed remarkable antiproliferative activity against the estrogen receptor (ER)-positive and estrogen-responsive human breast cancer cell line MCF-7. The activity was observed irrespective of the presence or absence of estrogen. The 5-aminoflavone derivatives (5-AFs) are not classical anti-estrogens because they did not compete with [H-3]estradiol to bind the estrogen receptor. Moreover, 5-AFs showed antitumor activity highly selective to the ER-positive breast cancer cell line, and they showed no effects against the ER-negative human cancer cell lines HeLa S-3, WiDr, and MDA-MB-453. Although the mechanism of their selective antitumor activity to ER-positive breast cancer cells is unclear, 5-AFs are expected to be a new type of antitumor agents in breast cancer.

  DOI：

  10.1021/jm950938g
• 作为产物：
  描述：

  对氰基苯乙酮 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.0h， 生成 N-[2-(4-cyanophenyl)-4-oxochromen-5-yl]-2,2-dimethylpropanamide
  参考文献：
  名称：

  Novel 5-Aminoflavone Derivatives as Specific Antitumor Agents in Breast Cancer

  摘要：

  In the course of our search for new antitumor agents in breast cancer, novel amino-substituted flavone derivatives were synthesized and examined for antitumor activities. Among them, 5,4'-diaminoflavone and some of its congeners showed remarkable antiproliferative activity against the estrogen receptor (ER)-positive and estrogen-responsive human breast cancer cell line MCF-7. The activity was observed irrespective of the presence or absence of estrogen. The 5-aminoflavone derivatives (5-AFs) are not classical anti-estrogens because they did not compete with [H-3]estradiol to bind the estrogen receptor. Moreover, 5-AFs showed antitumor activity highly selective to the ER-positive breast cancer cell line, and they showed no effects against the ER-negative human cancer cell lines HeLa S-3, WiDr, and MDA-MB-453. Although the mechanism of their selective antitumor activity to ER-positive breast cancer cells is unclear, 5-AFs are expected to be a new type of antitumor agents in breast cancer.

  DOI：

  10.1021/jm950938g