1-(2-hydroxyphenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone bromide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-hydroxyphenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone bromide
• 英文别名: 2-(4-Amino-1,2,4-triazol-4-ium-1-yl)-1-(2-hydroxyphenyl)ethanone;bromide
• 化学式: Br*C₁₀H₁₁N₄O₂
• 分子量: 299.127
• InChiKey: VYTGKQPXXIEYHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.52
• 重原子数：
  17
• 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：
  85
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone bromide 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 反应 0.75h， 生成 2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one
  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：

  2'-羟基苯乙酮 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 、 异丙醇 为溶剂， 生成 1-(2-hydroxyphenyl)-2-(4-amino-4H-1,2,4-triazoliumyl)ethanone bromide
  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

• 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.
• Synthesis, in vitro antifungal activity and in silico study of 3-(1,2,4-triazol-1-yl)flavanones
  作者：Saeed Emami、Shahaboddin Shojapour、Mohammad Ali Faramarzi、Nasrin Samadi、Hamid Irannejad

  DOI：10.1016/j.ejmech.2013.06.008

  日期：2013.8

  A series of novel 3-(1,2,4-triazol-1-yl)flavanones were synthesized based on the N-phenethylazole pharmacophore of azole antifungals. The results of antifungal assay revealed that 4'-fluoroflavanone derivative 4c exhibited the best profile of activity against Candida and Saccharomyces strains. Compound 4c was 4-16 times more potent than reference drug fluconazole against Candida albicans and Saccharomyces cerevisiae. The molecular docking study with lanosterol 14 alpha-demethylase, in silico toxicity risks and drug-likeness predictions were used to better define of title compounds as antifungal agents. The favorable drug-like property of compound 4c makes 3-(1,2,4-triazol-1-yl)flavanone prototype as a promising lead for the future development of azole antifungal agents. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis and Antifungal Activity of 1-[(2-Benzyloxy)Phenyl]-2-(Azol-1-yl)Ethanone Derivatives: Exploring the Scaffold Flexibility
  作者：Saeed Emami、Motahare Kazemi-Najafabadi、Soughra Pashangzadeh、Alireza Foroumadi、Mohammad Ali Faramarzi、Nasrin Samadi、Mehraban Falahati、Roohollah Fateh、Mahtab Ashrafi-Khozani

  DOI：10.1111/j.1747-0285.2011.01243.x

  日期：2011.12

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

  DOI：——

  日期：——