(E)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime | 144401-55-8

• 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: (E)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime
• 英文别名: 3-(1H-imidazolyl)-4-chromanone (4E)-oxime；3-Imidazol-1-ylchroman-4-one oxime；(NE)-N-(3-imidazol-1-yl-2,3-dihydrochromen-4-ylidene)hydroxylamine
• CAS: 144401-55-8
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: XNIOEJPXDHWIHV-WYMLVPIESA-N

物化性质

• 沸点：
  514.6±50.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-二氯氯苄 、 (E)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 (4E)-3-(1H-imidazol-1-yl)-2,3-dihydro-4H-chromen-4-one O-(3,4-dichlorobenzyl)oxime
  参考文献：
  名称：

  Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers

  摘要：

  A series of (E)- and (Z)-2,3-dihydro-3-(1 H-imidazol-1 -yl)-4H-1 -benzopyran-4-one oxime ethers have been synthesized and tested for antifungal activity Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)-3 d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)-(3 a) and (E)-3 a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.

  DOI：

  10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o
• 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 、 N,N-二甲基甲酰胺 为溶剂， 生成 (E)-2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one oxime
  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

• Azolylchromans as a novel scaffold for anticonvulsant activity
  作者：Saeed Emami、Abbas Kebriaeezadeh、Mohammad Jafar Zamani、Abbas Shafiee

  DOI：10.1016/j.bmcl.2006.01.004

  日期：2006.4

  A series of azolylchroman derivatives were prepared as conformationally constrained analogs of (arylalkyl)azole anticonvulsants. The anticonvulsant activities of the compounds were evaluated by determining seizure latency and protective effect against pentylenetetrazole (PTZ)-induced lethal convulsions in mice at a dose of 5 mg/kg. Among these compounds, 7-chloro-3-(1H-imidazol-1-yl)chroman-4-one and 3-(1H-1.2,4-triazol-1-yl)chroman-4-one exhibited significant action in delaying seizures as well as effective protection against PTZ-induced seizures and deaths. (C) 2006 Elsevier Ltd. All rights reserved.
• Imidazolylchromanone oxime ethers as potential anticonvulsant agents: Anticonvulsive evaluation in PTZ-kindling model of epilepsy and SAR study
  作者：Saeed Emami、Abbas Kebriaeezadeh、Nematollah Ahangar、Reza Khorasani

  DOI：10.1016/j.bmcl.2010.12.021

  日期：2011.1

  As a continuation of our efforts to develop the azolylchromanone derivatives as potential anticonvulsant agents, we explored (Z)- and (E)-oxime ether derivatives of imidazolylchromanones bearing different lipophilic O-benzyl groups and tested their anticonvulsant activities in PTZ-kindling model of epilepsy. O-(2,4-Dichlorobenzyl) oximes 8a, 16a and 20a were significantly effective in delaying the onset of the PTZ-evoked seizures at the dose of 30 mg/kg in kindled animals. The most effective compounds in delaying seizures were 7-chlorochromanone-O-(2,4-dichlorobenzyl) oximes 8a and 20a. SAR studies showed that introduction of a chlorine atom to the 7-position and/or a methyl group to the 2-position of the chroman ring resulted in an improvement of anti-seizure efficacy in O-(2,4-dichlorobenzyl) oxime series. (C) 2010 Elsevier Ltd. All rights reserved.
• US5246956A
  申请人：——

  公开号：US5246956A

  公开（公告）日：1993-09-21
• Stereoselective Synthesis and in Vitro Antifungal Evaluation of (E)- and (Z)-Imidazolylchromanone Oxime Ethers
  作者：Saeed Emami、Mehraban Falahati、Ali Banifatemi、Kayvan Moshiri、Abbas Shafiee

  DOI：10.1002/1521-4184(200209)335:7<318::aid-ardp318>3.0.co;2-o

  日期：2002.9

  A series of (E)- and (Z)-2,3-dihydro-3-(1 H-imidazol-1 -yl)-4H-1 -benzopyran-4-one oxime ethers have been synthesized and tested for antifungal activity Most compounds showed moderate to potent in vitro antifungal activity. Among the tested compounds, compound (E)-3 d was the most active agent against Candida albicans and Aspergillus niger, and compounds (Z)-(3 a) and (E)-3 a were the most potent compounds against Microsporum gypseum. Detailed stereoselective synthesis, spectroscopic, and biological data are reported.
• 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.