1-(2-羟基苯基)-2-(1,2,4-三唑-1-基)乙酮 | 111229-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-羟基苯基)-2-(1,2,4-三唑-1-基)乙酮
• 英文名称: 1-(2-hydroxyphenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
• 英文别名: 2'-hydroxy-2-(1,2,4-triazol-1-yl)acetophenone；1-(2-hydroxyphenyl)-2-(1,2,4-triazol-1-yl)ethanone
• CAS: 111229-09-5
• 化学式: C₁₀H₉N₃O₂
• 分子量: 203.2
• InChiKey: YVSQRWBRGKRJAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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-(2-羟基苯基)-2-(1,2,4-三唑-1-基)乙酮 在 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 (E)-trans-2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-2-methyl-4H-1-benzopyran-4-one O-(4-chlorophenylmethyl)oxime
  参考文献：
  名称：

  Synthesis, stereochemical and conformational properties of trans-2,3-dihydro-2-methyl-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one oxime ethers

  摘要：

  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.

  DOI：

  10.1016/j.tet.2005.01.054
• 作为产物：
  描述：

  2'-羟基苯乙酮 在 盐酸 、 copper(ll) bromide 、 sodium nitrite 作用下， 以 氯仿 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 1-(2-羟基苯基)-2-(1,2,4-三唑-1-基)乙酮
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 1-[(2-Benzyloxy)Phenyl]-2-(Azol-1-yl)Ethanone Derivatives: Exploring the Scaffold Flexibility

  摘要：

  Based on the N‐(phenethyl)azole backbone of azole antifungals, we designed 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3, containing benzyloxyphenyl scaffold of croconazole. Also these compounds can be considered as flexible analogs, resulted from C2–C3 disconnection of 3′‐chloro‐3‐imidazolylflavanone 1, recently described as antifungal agent. Thus, in this report, we describe the synthesis of 1‐[(2‐benzyloxy)phenyl]‐2‐(azol‐1‐yl)ethanone derivatives 2 and 3 and their biological evaluation against different pathogenic fungi. By comparing the antifungal activity profile of flexible compounds 2 and 3 with that of rigid analog 1, it can be inferred that lower susceptibilities (higher minimum inhibitory concentrations) were observed with flexible compounds. However, among the synthesized compounds, 1‐[2‐(2,4‐dichlorobenzyloxy)phenyl]‐2‐(1H‐imidazol‐1‐yl)ethanone hydrochloride (2g) showed comparable or more potent antifungal activity in comparison with fluconazole as a standard drug.

  DOI：

  10.1111/j.1747-0285.2011.01243.x

文献信息

• Fungicides
  申请人：Schering Agrochemicals Ltd.

  公开号：US04772613A1

  公开（公告）日：1988-09-20

  Compounds of any of one of formulae I-VII ##STR1## where is a single or double bond; A is oxygen or sulphur; R.sup.1 is aryl; R.sup.2 is 1-imidazolyl or 1,2,4-triazol-1-yl; and R.sup.3, R.sup.4, R.sup.5 and R.sup.6, which may be the same or different, are each hydrogen, halo, alkyl or alkoxy, have fungicidal activity.

  具有任一化学式I-VII中的任何一种化合物##STR1##其中n是单键或双键；A是氧或硫；R.sup.1是芳基；R.sup.2是1-咪唑基或1,2,4-三唑-1-基；R.sup.3、R.sup.4、R.sup.5和R.sup.6，它们可能相同也可能不同，每个都是氢、卤素、烷基或烷氧基，具有杀真菌活性。
• Benzoheterocyclic fungicides
  申请人：SCHERING AGROCHEMICALS LIMITED

  公开号：EP0247760A3

  公开（公告）日：1989-05-31

  Compounds of any one of formulae I - VII where.... is a single or double bond; A is oxygen or sulphur; R¹ is aryl; R² is 1-imidazolyl or 1,2,4-triazol-1-yl; and R³, R⁴, R⁵ and R⁶ which may be the same or different, are each hydrogen, halo, alkyl or alkoxy, have fungicidal activity.

  公式I - VII 中的任何一种化合物，其中....是单键或双键；A是氧或硫；R¹是芳基；R²是1-咪唑基或1,2,4-三唑-1-基；以及R³、R⁴、R⁵和R⁶可能相同也可能不同，分别是氢、卤素、烷基或烷氧基，具有杀真菌活性。
• 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.
• 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.