2-amino-7-diethylamino-4-(4-fluorophenyl)-4H-chromene-3-carbonitrile | 626221-06-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 2-amino-7-diethylamino-4-(4-fluorophenyl)-4H-chromene-3-carbonitrile
• 英文别名: 2-amino-4-(4-fluorophenyl)-7-(diethylamino)-4H-chromene-3-carbonitrile；2-amino-7-(diethylamino)-4-(4-fluorophenyl)-4H-chromene-3-carbonitrile
• CAS: 626221-06-5
• 化学式: C₂₀H₂₀FN₃O
• 分子量: 337.397
• InChiKey: VVAIKMXADATXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(4-氟亚苄基)-丙二腈 、 3-羟基-N,N-二乙基苯胺 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-amino-7-diethylamino-4-(4-fluorophenyl)-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis, Structure-Activity Relationship (SAR) Studies on some 4-Aryl-4Hchromenes and Relationship between Lipophilicity and Antitumor Activity

  摘要：

  通过3-取代酚1、4、6和8与α-氰基肉桂腈衍生物2的反应，获得了一些4-芳基-4H-色烯3a-h、5a-g、7a-g和9a-g。我们探讨了在4-和7-位进行修饰的4-芳基-4H-色烯的结构-活性关系（SAR）。使用微培养四唑盐（MTT）比色法，与标准药物长春碱和多柔比星相比，研究了合成的化合物的抗肿瘤活性。一些化合物显示出良好的体外抗肿瘤活性。结构-活性关系（SAR）研究发现，4-芳基-4H-色烯的抗肿瘤活性显著受到亲脂性、计算得到的Log P值以及7-亲水或疏水取代基与4-位苯环上的疏水取代基之间的平衡的影响。新制备的化合物的结构通过元素分析和光谱数据得到了确认。

  DOI：

  10.2174/1570180811666140623204655

文献信息

• Synthesis of 4H-chromene, coumarin, 12H-chromeno[2,3-d]pyrimidine derivatives and some of their antimicrobial and cytotoxicity activities
  作者：Nermien M. Sabry、Hany M. Mohamed、Essam Shawky A.E.H. Khattab、Shymaa S. Motlaq、Ahmed M. El-Agrody

  DOI：10.1016/j.ejmech.2010.12.015

  日期：2011.2

  Condensation of 3-N,N-diethylaminophenol (1) with alpha-cyanocinnamonitriles (2a-c) and ethyl alpha-cyanocinnamates (2d-f) provided compounds 3a-f and 4a-c. 12H-Chromeno[2,3-d]pyrimidine derivatives 6,11-13 and 16 were obtained by treatment of 4H-chromene compounds (3) with different electrophiles followed by nucleophilic reagents. Structures of these compounds were established on the basis of IR, UV, H-1 NMR, C-13 NMR and MS data. Some of the new compounds were evaluated for antimicrobial and cytotoxicity activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis, Structure-Activity Relationship (SAR) Studies on some 4-Aryl-4Hchromenes and Relationship between Lipophilicity and Antitumor Activity
  作者：Ahmed El-Agrody、Essam A. E. H. Khattab、Ahmed Fouda

  DOI：10.2174/1570180811666140623204655

  日期：2014.10.1

  Some 4-aryl-4H-chromenes 3a-h, 5a-g, 7a-g and 9a-g were obtained by reaction of 3-substituted phenol 1, 4, 6 and 8 with α-cyanocinnamonitrile derivatives 2. We explored the structure activity relationship (SAR) of 4-aryl-4Hchromenes with modification at the 4- and 7-positions. The antitumor activity of the synthesized compounds was investigated in comparison with the standard drugs Vinblastine and Doxorubicin using microculture tetrazolium (MTT) colorimetric assay. Some compounds were found to have good in vitro antitumor activity. The structure-activity relationship (SAR) study revealed that the antitumor activity of 4-aryl-4H-chromenes was significantly affected by the lipophilicity, the calculated Log P value and the balance between 7-hydrophilic or hydrophobic substituent and hydrophobic substituent on the benzene ring at 4-position. The structures of the newly prepared compounds were confirmed by elemental analysis and spectral data.

  通过3-取代酚1、4、6和8与α-氰基肉桂腈衍生物2的反应，获得了一些4-芳基-4H-色烯3a-h、5a-g、7a-g和9a-g。我们探讨了在4-和7-位进行修饰的4-芳基-4H-色烯的结构-活性关系（SAR）。使用微培养四唑盐（MTT）比色法，与标准药物长春碱和多柔比星相比，研究了合成的化合物的抗肿瘤活性。一些化合物显示出良好的体外抗肿瘤活性。结构-活性关系（SAR）研究发现，4-芳基-4H-色烯的抗肿瘤活性显著受到亲脂性、计算得到的Log P值以及7-亲水或疏水取代基与4-位苯环上的疏水取代基之间的平衡的影响。新制备的化合物的结构通过元素分析和光谱数据得到了确认。