(NE)-N-(3-bromo-2,3-dihydrochromen-4-ylidene)hydroxylamine | 1584214-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (NE)-N-(3-bromo-2,3-dihydrochromen-4-ylidene)hydroxylamine
• CAS: 1584214-39-0
• 化学式: C₉H₈BrNO₂
• 分子量: 242.072
• InChiKey: ASZYXYFNLRIUFA-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (NE)-N-(3-bromo-2,3-dihydrochromen-4-ylidene)hydroxylamine 在 硝酸 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 48.5h， 生成 (±)-(E)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one O-[2-(4-chlorophenoxy)ethyl]oxime nitrate
  参考文献：
  名称：

  Imidazolylchromanones containing non-benzylic oxime ethers: Synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii

  摘要：

  A series of imidazolylchromanone oximes containing phenoxyethyl ether moiety, as found in omoconazole, were synthesized and evaluated against yeasts (Candida albicans and Cryptococcus gattii) and filamentous fungi (Aspergillus fumigatus and Exophiala dermatitidis). Although the title compounds showed marginal activity against filamentous fungi but all of them exhibited potent activity against C gattii (MIC values <= 4 mu g/mL). Among them, (3-chlorophenoxy)ethyl analog 7c with MIC value of 0.5 mu g/mL was the most potent compound. Further molecular docking studies provided a better insight into the binding of designed compounds within the homology modeled active site of CnCYP51 (Cryptococcus CYP51-14 alpha-demethylase). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.019
• 作为产物：
  描述：

  3-溴-2,3-二氢色烯-4-酮 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成 (NE)-N-(3-bromo-2,3-dihydrochromen-4-ylidene)hydroxylamine
  参考文献：
  名称：

  Imidazolylchromanones containing non-benzylic oxime ethers: Synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii

  摘要：

  A series of imidazolylchromanone oximes containing phenoxyethyl ether moiety, as found in omoconazole, were synthesized and evaluated against yeasts (Candida albicans and Cryptococcus gattii) and filamentous fungi (Aspergillus fumigatus and Exophiala dermatitidis). Although the title compounds showed marginal activity against filamentous fungi but all of them exhibited potent activity against C gattii (MIC values <= 4 mu g/mL). Among them, (3-chlorophenoxy)ethyl analog 7c with MIC value of 0.5 mu g/mL was the most potent compound. Further molecular docking studies provided a better insight into the binding of designed compounds within the homology modeled active site of CnCYP51 (Cryptococcus CYP51-14 alpha-demethylase). (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.019

文献信息

• Imidazolylchromanones containing non-benzylic oxime ethers: Synthesis and molecular modeling study of new azole antifungals selective against Cryptococcus gattii
  作者：Mojtaba Babazadeh-Qazijahani、Hamid Badali、Hamid Irannejad、Mohammad Hosein Afsarian、Saeed Emami

  DOI：10.1016/j.ejmech.2014.02.019

  日期：2014.4

  A series of imidazolylchromanone oximes containing phenoxyethyl ether moiety, as found in omoconazole, were synthesized and evaluated against yeasts (Candida albicans and Cryptococcus gattii) and filamentous fungi (Aspergillus fumigatus and Exophiala dermatitidis). Although the title compounds showed marginal activity against filamentous fungi but all of them exhibited potent activity against C gattii (MIC values <= 4 mu g/mL). Among them, (3-chlorophenoxy)ethyl analog 7c with MIC value of 0.5 mu g/mL was the most potent compound. Further molecular docking studies provided a better insight into the binding of designed compounds within the homology modeled active site of CnCYP51 (Cryptococcus CYP51-14 alpha-demethylase). (C) 2014 Elsevier Masson SAS. All rights reserved.