1-(4-chloro-2-hydroxyphenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone | 402929-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-chloro-2-hydroxyphenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone
• 英文别名: 1-(4-chloro-2-hydroxyphenyl)-2-(1,2,4-triazol-4-yl)ethanone
• CAS: 402929-57-1
• 化学式: C₁₀H₈ClN₃O₂
• 分子量: 237.645
• InChiKey: ZEZAYTREVTXLGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-chloro-2-hydroxyphenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone 在 盐酸羟胺 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (Z)-7-chloro-2,3-dihydro-3-(4H-1,2,4-triazol-4-yl)-4H-1-benzopyran-4-one oxime
  参考文献：
  名称：

  Emami, Saeed; Shafiee, Abbas, Heterocycles, 2001, vol. 55, # 11, p. 2059 - 2074

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 反应 48.0h， 生成 1-(4-chloro-2-hydroxyphenyl)-2-(4H-1,2,4-triazol-4-yl)ethanone
  参考文献：
  名称：

  2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents

  摘要：

  2-Hydroxyphenacyl azole and 2-hydroxyphenacyl azolium compounds have been described as a new class of azole antifungals. Most target compounds showed significant in vitro antifungal activities against tested fungi (Candida albicans, Saccharomyces cerevisiae, Aspergillus niger, and Microsporum gypseum) with low MICs values included in the range of 0.25-32 mu g/mL comparable to reference drug fluconazole. The most active compounds were also assessed for their cytotoxicity using MTT colorimetric assay on normal mouse fibroblast (NIH/3T3) cells. The results of antifungal activity and toxicity tests indicated that these compounds display antifungal activity at non-cytotoxic concentrations. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.111

文献信息

• Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers
  作者：Saeed Emami、Mehraban Falahati、Ali Banifatemi、Abbas Shafiee

  DOI：10.1016/j.bmc.2004.08.030

  日期：2004.11

  A series of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers were stereoselectively synthesized and tested for in vitro antifungal activity. Many of these derivatives exhibit high activity against Candida albicans, Saccharomyces cerevisiae, Aspergillus niger, and Microsporum gypseum. (C) 2004 Elsevier Ltd. All rights reserved.
• Emami, Saeed; Shafiee, Abbas, Heterocycles, 2001, vol. 55, # 11, p. 2059 - 2074
  作者：Emami, Saeed、Shafiee, Abbas

  DOI：——

  日期：——
• Synthesis, stereochemical and conformational properties of trans-2,3-dihydro-2-methyl-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one oxime ethers
  作者：Saeed Emami、Abbas Shafiee

  DOI：10.1016/j.tet.2005.01.054

  日期：2005.3

  A convenient synthesis and structural characterization of (Z)- and (E)-trans-2,3-dihydro-2-methyl-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one oxime ethers has been achieved. By analysis of vicinal interproton coupling constants, it is believed that trans-2,3-dihydro-2-methyl-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-ones which exist predominantly in the diequatorial half-chair or sofa conformation was found to exist predominantly in the diaxial orientation upon conversion to the corresponding oxime ether derivatives. (C) 2005 Elsevier Ltd. All rights reserved.
• 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.
• 2-Hydroxyphenacyl azoles and related azolium derivatives as antifungal agents
  作者：Saeed Emami、Alireza Foroumadi、Mehraban Falahati、Ensieh Lotfali、Saeed Rajabalian、Soltan-Ahmed Ebrahimi、Shirin Farahyar、Abbas Shafiee

  DOI：10.1016/j.bmcl.2007.10.111

  日期：2008.1

  2-Hydroxyphenacyl azole and 2-hydroxyphenacyl azolium compounds have been described as a new class of azole antifungals. Most target compounds showed significant in vitro antifungal activities against tested fungi (Candida albicans, Saccharomyces cerevisiae, Aspergillus niger, and Microsporum gypseum) with low MICs values included in the range of 0.25-32 mu g/mL comparable to reference drug fluconazole. The most active compounds were also assessed for their cytotoxicity using MTT colorimetric assay on normal mouse fibroblast (NIH/3T3) cells. The results of antifungal activity and toxicity tests indicated that these compounds display antifungal activity at non-cytotoxic concentrations. (C) 2007 Elsevier Ltd. All rights reserved.