N-{3-[3-(3-Dimethylamino-phenyl)-3-oxo-propionyl]-4-hydroxy-phenyl}-acetamide | 179911-57-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-{3-[3-(3-Dimethylamino-phenyl)-3-oxo-propionyl]-4-hydroxy-phenyl}-acetamide
• 英文别名: N-[3-[3-[3-(dimethylamino)phenyl]-3-oxopropanoyl]-4-hydroxyphenyl]acetamide
• CAS: 179911-57-0
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: ZCKZQNIKUWQIOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-{3-[3-(3-Dimethylamino-phenyl)-3-oxo-propionyl]-4-hydroxy-phenyl}-acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到N-[2-(3-Dimethylamino-phenyl)-4-oxo-4H-chromen-6-yl]-acetamide; hydrochloride
  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：

  2-羟基-5-乙酰氨基苯乙酮 、 3-乙基-2-[(1E,3Z)-3-(3-乙基萘并[2,3-d][1,3]噻唑-2(3H)-亚基)-2-甲基-1-丙烯-1-基]萘并[2,3-d][1,3]噻唑-3-鎓溴化物-1,3-二[3-(二甲基氨基)苯基]-1,3-丙烷二酮(1:1:1) 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以44%的产率得到N-{3-[3-(3-Dimethylamino-phenyl)-3-oxo-propionyl]-4-hydroxy-phenyl}-acetamide
  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

文献信息

• Novel 5-Aminoflavone Derivatives as Specific Antitumor Agents in Breast Cancer
  作者：Tsutomu Akama、Yasushi Shida、Toru Sugaya、Hiroyuki Ishida、Katsushige Gomi、Masaji Kasai

  DOI：10.1021/jm950938g

  日期：1996.1.1

  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.