2-[4-(N-Acetyl)amino]phenyl-5-amino-4H-benzopyran-4-one

• 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: 2-[4-(N-Acetyl)amino]phenyl-5-amino-4H-benzopyran-4-one
• 英文别名: N-[4-(5-amino-4-oxochromen-2-yl)phenyl]acetamide
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: BKERKTJMMUANFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-(N-ethoxycarbonyl-N-pivaloyl)amino-6-(tetrahydropyran-2-yloxy)benzoate 在 吡啶 、 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 10.33h， 生成 2-[4-(N-Acetyl)amino]phenyl-5-amino-4H-benzopyran-4-one
  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

• 5- Aminoflavone derivatives
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0374789A1

  公开（公告）日：1990-06-27

  Novel 5-ammoflavone derivatives represented by formula (I) and pharmaceutically acceptable salts thereof are disclosed. The 5-aminoflavone derivatives have anticellular activity and are expected to be useful as antitumor agents.

  公开了由式（I）表示的新颖的5-氨基黄酮衍生物及其药用可接受的盐。这些5-氨基黄酮衍生物具有抗细胞活性，预计可用作抗肿瘤药物。
• 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.