| 1533457-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1533457-56-5
• 化学式: C₁₃H₂₂NO₄P
• 分子量: 287.296
• InChiKey: WIUPTWLGFSHBKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  70.78
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanoic acid 、 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 以70%的产率得到diethyl 1-((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)-1-(4-methoxyphenyl)ethylphosphonate
  参考文献：
  名称：

  Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding

  摘要：

  A series of novel coumarin-containing alpha-aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2-bromophenyl)methylphosphonate) was obtained. The in vitro antitumor activities of compound 8a-8g' against human pulmonary carcinoma cell line (A549), human nasopharyngeal carcinoma (human KB), and human lung adenocarcinoma (MGC-803) cell lines were evaluated. Some compounds showed relatively high cytotoxicity. Compared with 8g, 8g' exhibited an improved activity against three tumor cells, which was evidenced by the IC50 that was four- to five-fold lower than those for 8g. The influence of chirality was also observed in DNA-binding assay of 8g and 8g'. 8g' exhibited higher binding constant (1.96 x 10(3) M-1) as compared to 8g (1.69 x 10(3) M-1).

  DOI：

  10.1007/s00044-013-0899-3
• 作为产物：
  描述：

  diethyl (1-(4-methoxyphenyl)-1-((1-(4-methoxyphenyl)ethylidene)amino)ethyl)phosphonate 在 盐酸 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Coumarin-containing aminophosphonates bridged with chiral side chain: synthesis and influence of chirality on cytotoxicity and DNA binding

  摘要：

  A series of novel coumarin-containing alpha-aminophosphonates with two chiral centers were synthesized and a single-crystal structure of compound 8g (8g', (R)-diethyl ((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)(2-bromophenyl)methylphosphonate) was obtained. The in vitro antitumor activities of compound 8a-8g' against human pulmonary carcinoma cell line (A549), human nasopharyngeal carcinoma (human KB), and human lung adenocarcinoma (MGC-803) cell lines were evaluated. Some compounds showed relatively high cytotoxicity. Compared with 8g, 8g' exhibited an improved activity against three tumor cells, which was evidenced by the IC50 that was four- to five-fold lower than those for 8g. The influence of chirality was also observed in DNA-binding assay of 8g and 8g'. 8g' exhibited higher binding constant (1.96 x 10(3) M-1) as compared to 8g (1.69 x 10(3) M-1).

  DOI：

  10.1007/s00044-013-0899-3