N-[diethoxyphosphoryl-(4-methylphenyl)methyl]-3-fluoroaniline | 1446321-20-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[diethoxyphosphoryl-(4-methylphenyl)methyl]-3-fluoroaniline
• CAS: 1446321-20-5
• 化学式: C₁₈H₂₃FNO₃P
• 分子量: 351.358
• InChiKey: PMIZKJCTDDAFAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氟苯胺 、 对甲基苯甲醛 、 亚磷酸二乙酯 在 Amberlite-IR 120 作用下， 反应 0.02h， 以91%的产率得到N-[diethoxyphosphoryl-(4-methylphenyl)methyl]-3-fluoroaniline
  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

文献信息

• Efficient Bakers’ Yeast-Catalyzed Multicomponent Synthesis of <font>α</font>-Aminophosphonates in One Pot
  作者：Asish K. Bhattacharya、Mohammad Mujahid

  DOI：10.1080/00397911.2012.721918

  日期：2013.10.2

  Utilizing bakers' yeast (Saccharomyces cerevisiae) as a biocatalyst, synthesis of -aminophosphonates in one pot has been accomplished by the three-component reaction of an aldehyde, an amine, and diethyl phosphite in moderate to good yields under solvent-free reaction conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.
• Diversity-oriented synthesis of α-aminophosphonates: A new class of potential anticancer agents
  作者：Asish K. Bhattacharya、Dnyaneshwar S. Raut、Kalpeshkumar C. Rana、Innaiah K. Polanki、Mohd Sajid Khan、Sana Iram

  DOI：10.1016/j.ejmech.2013.05.036

  日期：2013.8

  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.