diethyl (3,7-dimethyl-1-(phenylamino)octa-2,6-dien-1-yl)phosphonate | 1027103-96-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl (3,7-dimethyl-1-(phenylamino)octa-2,6-dien-1-yl)phosphonate
• CAS: 1027103-96-3
• 化学式: C₂₀H₃₂NO₃P
• 分子量: 365.453
• InChiKey: ZSCAPMFMYOGJLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.38
• 重原子数：
  25.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯胺 、 亚磷酸二乙酯 、 柠檬醛 在 Amberlite-IR 120 作用下， 反应 0.02h， 以11%的产率得到diethyl (3,7-dimethyl-1-(phenylamino)octa-2,6-dien-1-yl)phosphonate
  参考文献：
  名称：

  Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents

  摘要：

  A small library of structurally diverse alpha-aminophosphonates has been synthesized by reacting alkyl/aryl aldehydes, alkyl/aryl amines and alkyl/aryl phosphites in one-pot catalyzed by Amberlite-IR 120 resin (acidic). All the synthesized alpha-aminophosphonates were assayed for their in vitro cytotoxic activities against a panel of five human cancer cell lines including A-549, NCI-H23 (Lung), Colo 320DM (Colon), MG-63 (Bone marrow) and Jurkat (Blood T lymphocytes). Compound 4n having (R)-1-phenylethanamine was found to be the most active amongst all the synthesized alpha-aminophosphonates against all the five cancer cell lines, most prominent being against Jurkat cell line with an IC50 value of 4 mu M. Surprisingly, compound 4o having (S)-1-phenylethanamine was found to be devoid of any cytotoxicity. Our finding suggests that these chemical entities could further serve as interesting template for the design of potential anticancer agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.036