2-(4-氯-3-硝基苯基)-1,3-苯并恶唑 | 32058-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氯-3-硝基苯基)-1,3-苯并恶唑
• 英文名称: 2-(4-chloro-3-nitrophenyl)benzo[d]oxazole
• 英文别名: 2-(4-chloro-3-nitrophenyl)benzooxazole；2-(4-chloro-3-nitro-phenyl)-benzooxazole；2-(4-Chloro-3-nitro-phenyl)-benzoxazol；2-(4-Chlor-3-nitro-phenyl)-benzoxazol；Benzoxazole, 2-(4-chloro-3-nitrophenyl)-；2-(4-chloro-3-nitrophenyl)-1,3-benzoxazole
• CAS: 32058-60-9
• 化学式: C₁₃H₇ClN₂O₃
• 分子量: 274.663
• InChiKey: VIWOIEIZTTXVGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(4-氯-3-硝基苯基)-1,3-苯并恶唑 在 palladium 10% on activated carbon 、 氯化锆(IV) 、 potassium carbonate 、 肼 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV

  摘要：

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.

  DOI：

  10.1021/jm100912b
• 作为产物：
  描述：

  4-氯-N-(2-羟基苯基)-3-硝基苯甲酰胺 以 neat (no solvent) 为溶剂， 反应 2.0h， 生成 2-(4-氯-3-硝基苯基)-1,3-苯并恶唑
  参考文献：
  名称：

  A microwave assisted synthesis of benzoxazoles from carboxylic acids

  摘要：

  A series of various poly-substituted benzoxazoles were synthesized starting from readily available carboxylic acids. The method is based on TCT (cyanuric chloride)/microwave acid activation and it is characterized by mild conditions, allowing for a wide range of starting materials and functionalization of final products. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.10.084

文献信息

• Samarium(III) triflate: a new catalyst for facile synthesis of benzothiazoles and benzoxazoles from carboxylic acids in aqueous media
  作者：Pratapsinha B. Gorepatil、Yogesh D. Mane、Amarsinha B. Gorepatil、Mahadev V. Gaikwad、Vilas S. Ingle

  DOI：10.1007/s11164-014-1897-x

  日期：2015.11

  A facile synthetic method for benzothiazoles and benzoxazoles comprising the reaction of corresponding 2-aminothiophenol and 2-aminophenol with various substituted aromatic carboxylic acids using Samarium(III) triflate as a catalyst has been described. The advantages of the method are short reaction times and aqueous reaction media and easy work-up. The catalysts can be recovered for the subsequent reactions and reused without any appreciable loss of efficiency.

  介绍了一种苯并噻唑和苯并恶唑的简便合成方法，包括使用三酸钐(III)作为催化剂，使相应的 2-氨基苯硫酚和 2-氨基苯酚与各种取代的芳香族羧酸反应。该方法的优点是反应时间短，采用水性反应介质，易于操作。催化剂可回收用于后续反应，并可重复使用，而不会明显降低效率。
• Rips,R. et al., Chimica Therapeutica, 1971, vol. 6, p. 126 - 130
  作者：Rips,R. et al.

  DOI：——

  日期：——
• A microwave assisted synthesis of benzoxazoles from carboxylic acids
  作者：Giammario Nieddu、Giampaolo Giacomelli

  DOI：10.1016/j.tet.2012.10.084

  日期：2013.1

  A series of various poly-substituted benzoxazoles were synthesized starting from readily available carboxylic acids. The method is based on TCT (cyanuric chloride)/microwave acid activation and it is characterized by mild conditions, allowing for a wide range of starting materials and functionalization of final products. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV
  作者：Qi Sun、Runzhi Wu、Sutang Cai、Yuan Lin、Llewlyn Sellers、Kaori Sakamoto、Biao He、Blake R. Peterson

  DOI：10.1021/jm100912b

  日期：2011.3.10

  Inhibitors of the PI3-kinase/AKT (protein kinase B) pathway are under investigation as anticancer and antiviral agents. The benzimidazole derivative AKT inhibitor-IV (ChemBridge 5233705) affects this pathway and exhibits potent anticancer and antiviral activity. To probe its biological activity, we synthesized AKT inhibitor-IV and 21 analogues using a novel six-step route based on ZrCl4-catalyzed cyclization of 1,2-arylenediamines with alpha,beta-unsaturated aldehydes. We examined effects on viability of HeLa carcinoma cells, viability of normal human cells (NHBE), replication of recombinant parainfluenza virus 5 (PIV5) in HeLa cells, and replication of the intracellular bacterium Mycobacterium fortuitum in HeLa cells. Replacement of the benzimidazole N-ethyl substitutent of AKT inhibitor-IV with N-hexyl and N-dodecyl groups enhanced antiviral activity and cytotoxicity against the cancer cell line, but these compounds showed substantially lower toxicity (from 6-fold to >20-fold) against NHBE cells and no effect on M. fortuitum, suggesting inhibition of one or more host protein(s) required for proliferation of cancer cells and PIV5. The key structural elements identified here may facilitate identification of targets of this highly biologically active scaffold.