3-amino-7-(benzyloxy)-2H-chromen-2-one | 1573010-11-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-amino-7-(benzyloxy)-2H-chromen-2-one
• 英文别名: 3-Amino-7-benzyloxycoumarin；3-amino-7-phenylmethoxychromen-2-one
• CAS: 1573010-11-3
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: NUYXPGAKYBVYHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-7-(benzyloxy)-2H-chromen-2-one 在 盐酸 、 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到3-氨基-7-羟基香豆素
  参考文献：
  名称：

  Defining a minimum pharmacophore for simocyclinone D8 disruption of DNA gyrase binding to DNA

  摘要：

  DOI：

  10.1007/s00044-014-0942-z
• 作为产物：
  描述：

  3-acetamido-2-oxo-2H-chromen-7-yl acetate 在 4-二甲氨基吡啶 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 3-amino-7-(benzyloxy)-2H-chromen-2-one
  参考文献：
  名称：

  Defining a minimum pharmacophore for simocyclinone D8 disruption of DNA gyrase binding to DNA

  摘要：

  DOI：

  10.1007/s00044-014-0942-z

文献信息

• Synthesis and Anti-Cancer Activities of Aryl Benzyl Ethers with Fluoro Substituents
  作者：Yi Jiang、Hong Xu、Li Liu、Rui He、Xiaomei Song、Na Li

  DOI：10.2174/1570180811666140130232233

  日期：2014.5.31

  A series of aryl benzyl ethers with fluoro substituents were synthesized and their structures were confirmed by spectral. All the compounds were tested for their cytotoxic activity in vitro against two human tumor cell lines: A549, SGC7901, and most showed cytotoxicity. Compound 10 was the most active in suppressing the growth of both screened cancer cells.

  合成了一系列具有氟取代基的芳基苄基醚，并通过光谱证实了其结构。测试了所有化合物在体外对两种人类肿瘤细胞系：A549，SGC7901的细胞毒性活性，并且大多数显示出细胞毒性。化合物10在抑制两种筛选的癌细胞的生长中最活跃。
• Novobiocin–ferrocene conjugates possessing anticancer and antiplasmodial activity independent of HSP90 inhibition
  作者：Mziyanda Mbaba、Jo-Anne de la Mare、Jason N. Sterrenberg、Deborah Kajewole、Shantal Maharaj、Adrienne L. Edkins、Michelle Isaacs、Heinrich C. Hoppe、Setshaba D. Khanye

  DOI：10.1007/s00775-018-1634-9

  日期：2019.3

  A series of tailored novobiocin-ferrocene conjugates was prepared in moderate yields and investigated for in vitro anticancer and antiplasmodial activity against the MDA-MB-231 breast cancer line and Plasmodium falciparum 3D7 strain, respectively. While the target compounds displayed moderate anticancer activity against the breast cancer cell line with IC50 values in the mid-micromolar range, compounds 10a-c displayed promising antiplasmodial activity as low as 0.889 mu M. Furthermore, the most promising compounds were tested for inhibitory effects against a postulated target, heat shock protein 90 (Hsp90).Graphical abstract A selection of tailored novobiocin derivatives bearing the organometallic ferrocene unit were synthesized and characterized by common spectroscopic techniques. The target compounds were investigated for in vitro anticancer and antimalarial activity against the MDA-MB-231 breast cancer cell line and Plasmodium falciparum 3D7 strain, respectively.[GRAPHICS].