1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate | 57432-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate
• 英文别名: 1-[2-(2,4-Dichlorophenyl)-2-oxoethyl]-1H-imidazole mononitrate；1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanone;nitric acid
• CAS: 57432-73-2
• 化学式: C₁₁H₈Cl₂N₂O*HNO₃
• 分子量: 318.116
• InChiKey: HRDAQQLDAVZFAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate 生成 2’-(1H-咪唑-1-基)-2,4-二氯苯乙酮
  参考文献：
  名称：

  MILLER, G. A.

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-二氯苯乙酮 、 咪唑 生成 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanone nitrate
  参考文献：
  名称：

  MILLER, G. A.

  摘要：

  DOI：

文献信息

• Conversion of 4-amino-4<i>H</i>-1,2,4-triazole to 1,3-bis(1<i>H</i>-azol-l-yl)-2-aryl-2-propanols and 1-phenacyl-4-[(benzoyl or 4-toluenesulfonyl)-imino]-(1<i>H</i>-1,2,4-triazolium) Ylides
  作者：Anjana Narayanan、David R. Chapman、Subhash P. Upadhyaya、Ludwig Bauer

  DOI：10.1002/jhet.5570300538

  日期：1993.10

  A series of 1,3-bis(1H-azol-1-yl)-2-aryl-2-propanols 17 were synthesized in an one-pot procedure by reacting l-aryl-2-(1H-1,2,4-triazol-l-yl)- or l-aryl-2-(1H-imidazol-l-yl)ethanones with dimethylsulfoxonium methide in the presence of either 1,2,4-triazole or imidazole. The aromatic groups in 17 were either 4-bromo-, 4-chloro-, 2,4-dichloro- or 2,4-difluorophenyl. 4-Amino-4H-1,2,4-triazole was acylated

  通过一锅法通过使1-芳基-2-（1 H -1,2）反应，合成一系列1,3-双（1 H -azol-1-基）-2-芳基-2-丙醇17。在1,2,4-三唑或咪唑存在下，与4-甲基二甲基亚砜基合成的1-，4-三唑-1-基）-或1-芳基-2-（1 H-咪唑-1-基）乙酮。17中的芳族基团是4-溴-，4-氯-，2,4-二氯-或2,4-二氟苯基。将4-氨基-4 H -1,2,4-三唑用苯甲酰基或4-甲苯磺酰氯酰化，得到[4-（苯甲酰基或4-甲苯磺酰基）氨基] 4 H-1,2,4-三唑 随后用4-溴或4-氯苯甲酰基溴进行烷基化，生成1-（4-溴或4-氯苯甲酰基）-4-[（苯甲酰基-或4-甲苯磺酰基）氨基] -1 H -1,2,4-三唑鎓溴化物。这些盐的中和提供了相应的酰化物。
• Synthesis, Antifungal Activity, and Molecular Modeling Studies of New Inverted Oxime Ethers of Oxiconazole
  作者：Armando Rossello、Simone Bertini、Annalina Lapucci、Marco Macchia、Adriano Martinelli、Simona Rapposelli、Esperanza Herreros、Bruno Macchia

  DOI：10.1021/jm020980t

  日期：2002.10.1

  Some new oxime ethers of types 7 and 8, in which the methyleneaminoxy group, C=N-O, of oxiconazole 6 is in an inverted atomic sequence, were synthesized and tested for their antifungal activities. Among them, the type 7 compounds, such as the N-ethoxy-morpholino-substituted derivatives 71-o (Table 1), showed good antifungal properties against the Candida strains tested, with minimum inhibitory concentration (MIC) values similar to those of the reference drug 6. A remarkable result was obtained with these types of azoles, which had shown a cidal character against Candida albicans, while the reference drug oxiconazole was only fungistatic in the same tests. This fact may be seen from a comparison of the MIC values with those of the minimum fungicidal concentration (MFC) values for most of the type 7 compounds assayed that have shown differences between the MIC and the MFC, which are lower than three double diluitions. A simple molecular modeling of the P450 14-alpha-sterol demethylase from C. albicans (Candida P450DM) was built in order to understand how the structural differences between type 7 compounds and oxiconazole 6 can induce different antifungal profiles. The results of this work seem to confirm that it is possible to reverse the atomic sequence of the methyleneaminoxy group, C=N-O, of 6, obtaining new imidazoles possessing good antifungal properties.