5-nitrofuran-2-carboxaldehyde-N₄-methyl-N₄-cyclohexylthiosemicarbazone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-nitrofuran-2-carboxaldehyde-N₄-methyl-N₄-cyclohexylthiosemicarbazone
• 英文别名: 1-cyclohexyl-1-methyl-3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]thiourea
• 化学式: C₁₃H₁₈N₄O₃S
• 分子量: 310.377
• InChiKey: ABYVIVGUNRMBNG-ZROIWOOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-硝基糠醛 、 4-cyclohexyl-4-methyl-3-thiosemicarbazide 以 乙醇 、 水 为溶剂， 反应 3.0h， 以70%的产率得到5-nitrofuran-2-carboxaldehyde-N₄-methyl-N₄-cyclohexylthiosemicarbazone
  参考文献：
  名称：

  Novel bidentate complexes of Cu(II) derived from 5-nitrofuran-2-carboxaldehyde thiosemicarbazones with antiamoebic activity against E. histolytica

  摘要：

  The novel analogues of 5-nitrofuran-2-carboxaldehyde thiosernicarbazones 1-10 were synthesized and their copper(H) complexes 1a-10a were obtained by means of coordination with cupric chloride. All these compounds have been characterized by elemental analysis, IR, electronic spectra and thermogravimetric patterns while ligands have also been characterized by H-1 NMR spectral studies. These copper complexes are bidentate and possess octahedral geometry around Cu(II) ion. Their antiamoebic activities were carried out to ascertain their effectiveness in comparison to their corresponding thiosemicarbazones. A number of these complexes possess noteworthy potencies towards HK-9 strain of Entainoeba histolytica in vitro. The complexes 2a-7a, 9a and 10a showed less IC50 value than metronidazole, the drug of choice for amoebiasis. Moreover, complexes 2a and 9a have shown the most promising antiamoebic activities (IC50 = 0.38 mu M of 2a and IC50 = 0.34 mu M of 9a versus IC50 = 1.81 mu M of metronidazole). These results indicate that the metallated thiosemicarbazone may be lead molecule to inhibit growth of E. histolytica. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.01.003

文献信息

• Novel bidentate complexes of Cu(II) derived from 5-nitrofuran-2-carboxaldehyde thiosemicarbazones with antiamoebic activity against E. histolytica
  作者：Sangita Sharma、Fareeda Athar、Mannar R. Maurya、Fehmida Naqvi、Amir Azam

  DOI：10.1016/j.ejmech.2005.01.003

  日期：2005.6

  The novel analogues of 5-nitrofuran-2-carboxaldehyde thiosernicarbazones 1-10 were synthesized and their copper(H) complexes 1a-10a were obtained by means of coordination with cupric chloride. All these compounds have been characterized by elemental analysis, IR, electronic spectra and thermogravimetric patterns while ligands have also been characterized by H-1 NMR spectral studies. These copper complexes are bidentate and possess octahedral geometry around Cu(II) ion. Their antiamoebic activities were carried out to ascertain their effectiveness in comparison to their corresponding thiosemicarbazones. A number of these complexes possess noteworthy potencies towards HK-9 strain of Entainoeba histolytica in vitro. The complexes 2a-7a, 9a and 10a showed less IC50 value than metronidazole, the drug of choice for amoebiasis. Moreover, complexes 2a and 9a have shown the most promising antiamoebic activities (IC50 = 0.38 mu M of 2a and IC50 = 0.34 mu M of 9a versus IC50 = 1.81 mu M of metronidazole). These results indicate that the metallated thiosemicarbazone may be lead molecule to inhibit growth of E. histolytica. (c) 2005 Elsevier SAS. All rights reserved.