2-amino-6-chloro-4-(4-fluorophenyl)-4H-benzo[h]chromene-3-carbonitrile | 331857-67-1

• 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-6-chloro-4-(4-fluorophenyl)-4H-benzo[h]chromene-3-carbonitrile
• CAS: 331857-67-1
• 化学式: C₂₀H₁₂ClFN₂O
• 分子量: 350.779
• InChiKey: XLNRIWZDWNGWDG-UHFFFAOYSA-N

物化性质

• 沸点：
  552.0±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-4-(4-fluorophenyl)-4H-benzo[h]chromene-3-carbonitrile 在 氨 、 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 N'-[6-chloro-3-cyano-4-(4-fluorophenyl)-4H-benzo[h]chromen-2-yl]methanimidamide
  参考文献：
  名称：

  Synthesis of halogen derivatives of benzo[h]chromene and benzo[a]anthracene with promising antimicrobial activities

  摘要：

  The synthesis of novel 7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene derivatives has been reported. The key intermediate 3-amino-9-chloro-1-(4-halophenyl)-1H-benzo[h]chromene-2-carbonitrile (3) was obtained by treating 4-halobenzylidenmalononitriles (la-c) and ethyl 4-halobenzylidenmalonates (1d-f) with 4-chloro-1-naphthol (2) in ethanolic piperidine solution. Antimicrobial activity was shown for most of the synthesized compounds. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01263-6
• 作为产物：
  描述：

  2-(benzylideneamino)-6-chloro-4-(4-fluorophenyl)-4H-benzo[h]chromene-3-carbonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 2-amino-6-chloro-4-(4-fluorophenyl)-4H-benzo[h]chromene-3-carbonitrile
  参考文献：
  名称：

  Synthesis of halogen derivatives of benzo[h]chromene and benzo[a]anthracene with promising antimicrobial activities

  摘要：

  The synthesis of novel 7-(4-halophenyl)-8,9-dihydro-7H-12-oxa-9,11-diaza-benzo[a]anthracene derivatives has been reported. The key intermediate 3-amino-9-chloro-1-(4-halophenyl)-1H-benzo[h]chromene-2-carbonitrile (3) was obtained by treating 4-halobenzylidenmalononitriles (la-c) and ethyl 4-halobenzylidenmalonates (1d-f) with 4-chloro-1-naphthol (2) in ethanolic piperidine solution. Antimicrobial activity was shown for most of the synthesized compounds. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01263-6

文献信息

• Synthesis, antitumor activity of 2-amino-4H-benzo[h]chromene derivatives, and structure–activity relationships of the 3- and 4-positions
  作者：Ahmed M. El-Agrody、Ahmed M. Fouda、Essam Shawky A. E. H. Khattab

  DOI：10.1007/s00044-013-0602-8

  日期：2013.12

  4-chloro-1-naphthol (1) with α-cyanocinnamonitrile (2a–i) or ethyl α-cyanocinnamate derivatives (4a–h), respectively. Structures of these compounds were established on the basis of spectral data. The antitumor activity of the synthesized compounds was investigated in comparison with Vinblastine, Colchicine, and Doxorubicin well-known anticancer drugs, using MTT colorimetric assay. Among them, the compounds

  通过4-氯-1-萘酚（1）与α-氰基肉桂腈（2a - i）或乙基的反应获得了几个2-氨基-4 H-苯并[ h ]色酮（3a – i）和（5a – h）。α-氰基肉桂酸酯衍生物（4a – h）。这些化合物的结构是根据光谱数据确定的。使用MTT比色法，与长春碱，秋水仙碱和阿霉素众所周知的抗癌药物进行了比较，研究了合成化合物的抗肿瘤活性。其中，化合物5e，图3c，图5F，b，d，3D，图5c，一个是最有效对抗MCF-7，5A针对HCT-116和图5a，图3e，一个针对人肝癌HepG-2与标准药物长春碱相比，而化合物5E，3c，5f，b，d，3d，5c，a，h，3i，g，a，e对HCT- 116、5a，3e，a，5e，3c对MCF- 7、5a，c，e，f，b，3e，c，g，b，5d，h，3d，i，5g最活跃，5d，c，f，3b，5g，3g，5h与标准药物秋水仙碱相比，它能抵抗HepG-2。讨论了3位和4位的结构活性关系。