1-(4-Chlorophenyl)-1-diethoxyphosphorylethanamine | 1533457-55-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-Chlorophenyl)-1-diethoxyphosphorylethanamine
• CAS: 1533457-55-4
• 化学式: C₁₂H₁₉ClNO₃P
• 分子量: 291.715
• InChiKey: JENGRUDJFDOFGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanoic acid 、 1-(4-Chlorophenyl)-1-diethoxyphosphorylethanamine 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75%的产率得到diethyl 1-((S)-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)propanamido)-1-(4-chlorophenyl)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：

  对氯苯乙酮 在 盐酸 、 ammonium acetate 作用下， 以 乙醚 为溶剂， 反应 11.5h， 生成 1-(4-Chlorophenyl)-1-diethoxyphosphorylethanamine
  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

文献信息

• Compound, Manufacturing Method Therefor, and Method for Manufacturing Optically Active alpha-Aminophosphonate Derivative
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：US20160145278A1

  公开（公告）日：2016-05-26

  A method for producing a compound represented by General Formula (1), the method including: reacting a compound represented by General Formula (3) and a compound represented by General Formula (4): where R 1 and R 2 each represent aliphatic group which may have substituent, or aromatic group which may have substituent (with the proviso that R 1 and R 2 are different groups), R 3 represents aromatic group which may have substituent, and R 4 represents aliphatic group which may have substituent, or aromatic group which may have substituent, where R 1 and R 2 each represent aliphatic group which may have substituent, or aromatic group which may have substituent (with the proviso that R 1 and R 2 are different groups), and R 3 represents aromatic group which may have substituent, where R 4 represents aliphatic group which may have substituent, or aromatic group which may have substituent.

  一种制备通式（1）所代表化合物的方法，包括：反应通式（3）所代表的化合物和通式（4）所代表的化合物：其中R1和R2分别代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团（前提是R1和R2是不同的基团），R3代表可能具有取代基的芳香族基团，R4代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团，其中R1和R2分别代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团（前提是R1和R2是不同的基团），R3代表可能具有取代基的芳香族基团，R4代表可能具有取代基的脂肪族基团或可能具有取代基的芳香族基团。
• US9493492B2
  申请人：——

  公开号：US9493492B2

  公开（公告）日：2016-11-15