(1Z,2E)-2-{[(3-methylbenzofuran-2-yl)carbonyl]hydrazono}-N-(4-bromophenyl)propanehydrazonoyl chloride | 1204683-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (1Z,2E)-2-{[(3-methylbenzofuran-2-yl)carbonyl]hydrazono}-N-(4-bromophenyl)propanehydrazonoyl chloride
• 英文别名: (1Z,2E)-N-(4-bromophenyl)-2-[(3-methyl-1-benzofuran-2-carbonyl)hydrazinylidene]propanehydrazonoyl chloride
• CAS: 1204683-05-5
• 化学式: C₁₉H₁₆BrClN₄O₂
• 分子量: 447.719
• InChiKey: JWFKMPCDGMGALP-SZQFWKLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  79
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌啶 、 (1Z,2E)-2-{[(3-methylbenzofuran-2-yl)carbonyl]hydrazono}-N-(4-bromophenyl)propanehydrazonoyl chloride 、 4-氯苯甲醛 以 乙醇 为溶剂， 反应 8.0h， 以70%的产率得到(1E,2Z,3E)-1-(piperidin-1-yl)-1-[(4-bromophenyl)hydrazono]-2-[(3-methylbenzofuran-2-oyl)hydrazono]-4-(4-chlorophenyl)but-3-ene
  参考文献：
  名称：

  Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones

  摘要：

  The reaction of 2-oxo-N-arylpropanehydrazonoyl chlorides 3a-e with 3-methyl-2-benzofurancarboxylic acid hydrazide (7) furnished N-(aryl)propanehydrazonoyl chlorides 8a-e. X-Ray of 8c revealed the (1Z,2E) configuration of structure 8. Nucleophilic substitution reaction of 8a or 8d with piperidine resulted in the formation of 1-(piperidin-1-yl)-N-2-arylamidrazones 9a, b. The X-ray diffraction of 9b showed its (I E,2E) configuration and it confirmed the stereoselectivity of the latter reaction. (1E,2Z,3E)-1 -(Piperidin-1-yl)-1-(arylhydrazono)-2-[(3-methylbenzofuran-2-oyl)hydrazonol-4-arylbut-3-enes 11 were synthesized in stereoselective reaction from 8 or alternatively from 9. X-ray analysis of 11b showed a conversion of configuration respect to 8d or 9b. X-Ray analysis of 9b, and 11b revealed the role of hydrogen interactions in the stereochemistry of their solid state structure. The in vitro antimicrobial activity of the newly synthesized compounds demonstrated an excellent growth inhibition of compounds 9 and 11 against clinically isolated strains of human fungal pathogens and exhibited a significant potency against Gram-positive bacteria. Griseofulvin and Amoxicilline were used as references for antifungal and antibacterial screening. The effect of most potent antifungal compound 9b on morphological features of Aspergillus fumigatus and Candida albicans using image analyzer was studied. Furthermore, the effect of 9b on the ultra-structures of the latter fungi was occurred by transmission electron microscope. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.002
• 作为产物：
  描述：

  3-甲基苯并呋喃-2-羧酸肼 、 3-[(4-溴苯基)肼基]-3-氯丙-2-酮 以 四氢呋喃 为溶剂， 反应 11.0h， 以80%的产率得到(1Z,2E)-2-{[(3-methylbenzofuran-2-yl)carbonyl]hydrazono}-N-(4-bromophenyl)propanehydrazonoyl chloride
  参考文献：
  名称：

  Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones

  摘要：

  The reaction of 2-oxo-N-arylpropanehydrazonoyl chlorides 3a-e with 3-methyl-2-benzofurancarboxylic acid hydrazide (7) furnished N-(aryl)propanehydrazonoyl chlorides 8a-e. X-Ray of 8c revealed the (1Z,2E) configuration of structure 8. Nucleophilic substitution reaction of 8a or 8d with piperidine resulted in the formation of 1-(piperidin-1-yl)-N-2-arylamidrazones 9a, b. The X-ray diffraction of 9b showed its (I E,2E) configuration and it confirmed the stereoselectivity of the latter reaction. (1E,2Z,3E)-1 -(Piperidin-1-yl)-1-(arylhydrazono)-2-[(3-methylbenzofuran-2-oyl)hydrazonol-4-arylbut-3-enes 11 were synthesized in stereoselective reaction from 8 or alternatively from 9. X-ray analysis of 11b showed a conversion of configuration respect to 8d or 9b. X-Ray analysis of 9b, and 11b revealed the role of hydrogen interactions in the stereochemistry of their solid state structure. The in vitro antimicrobial activity of the newly synthesized compounds demonstrated an excellent growth inhibition of compounds 9 and 11 against clinically isolated strains of human fungal pathogens and exhibited a significant potency against Gram-positive bacteria. Griseofulvin and Amoxicilline were used as references for antifungal and antibacterial screening. The effect of most potent antifungal compound 9b on morphological features of Aspergillus fumigatus and Candida albicans using image analyzer was studied. Furthermore, the effect of 9b on the ultra-structures of the latter fungi was occurred by transmission electron microscope. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.09.002

文献信息

• Stereoselective synthesis and antimicrobial activity of benzofuran-based (1E)-1-(piperidin-1-yl)-N2-arylamidrazones
  作者：Hatem A. Abdel-Aziz、Amal A.I. Mekawey

  DOI：10.1016/j.ejmech.2009.09.002

  日期：2009.12

  The reaction of 2-oxo-N-arylpropanehydrazonoyl chlorides 3a-e with 3-methyl-2-benzofurancarboxylic acid hydrazide (7) furnished N-(aryl)propanehydrazonoyl chlorides 8a-e. X-Ray of 8c revealed the (1Z,2E) configuration of structure 8. Nucleophilic substitution reaction of 8a or 8d with piperidine resulted in the formation of 1-(piperidin-1-yl)-N-2-arylamidrazones 9a, b. The X-ray diffraction of 9b showed its (I E,2E) configuration and it confirmed the stereoselectivity of the latter reaction. (1E,2Z,3E)-1 -(Piperidin-1-yl)-1-(arylhydrazono)-2-[(3-methylbenzofuran-2-oyl)hydrazonol-4-arylbut-3-enes 11 were synthesized in stereoselective reaction from 8 or alternatively from 9. X-ray analysis of 11b showed a conversion of configuration respect to 8d or 9b. X-Ray analysis of 9b, and 11b revealed the role of hydrogen interactions in the stereochemistry of their solid state structure. The in vitro antimicrobial activity of the newly synthesized compounds demonstrated an excellent growth inhibition of compounds 9 and 11 against clinically isolated strains of human fungal pathogens and exhibited a significant potency against Gram-positive bacteria. Griseofulvin and Amoxicilline were used as references for antifungal and antibacterial screening. The effect of most potent antifungal compound 9b on morphological features of Aspergillus fumigatus and Candida albicans using image analyzer was studied. Furthermore, the effect of 9b on the ultra-structures of the latter fungi was occurred by transmission electron microscope. (C) 2009 Elsevier Masson SAS. All rights reserved.