1-[[2-(3,4-Dichlorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole | 1395882-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[[2-(3,4-Dichlorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole
• CAS: 1395882-26-4
• 化学式: C₁₁H₉Cl₂N₃O
• 分子量: 270.118
• InChiKey: PSGTYHJDBBORSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6-二溴咔唑 、 1-[[2-(3,4-Dichlorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以42.1%的产率得到1-(3,6-dibromo-9H-carbazol-9-yl)-2-(3,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl) propan-2-ol
  参考文献：
  名称：

  Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungi

  摘要：

  A series of carbazole-triazole conjugates were designed, synthesized and characterized by IR, NMR, and HRMS spectra. Biological assay showed that most of the synthesized compounds exhibited moderate and even strong antifungal activities, especially 3,6-dibromocarbazolyl triazole 5d displayed excellent inhibitory efficacy against most of the tested fungal strains (MIC = 2-32 mu g/mL) and effectively fungicidal ability towards C albicans, C tropicals and C. parapsilosis ATCC 22019 (MFC = 4-8 mu g/mL). Its combination use with fluconazole could enhance the antifungal efficacy, and compound 5d also did not obviously trigger the development of resistance in C. albicans even after 10 passages. Preliminary mechanism study revealed that the active molecule 5d could depolarize fungal membrane potential and intercalate into DNA to possibly block DNA replication, thus possibly exhibiting its powerful antifungal abilities. Conjugate 5d could interact with HSA, which was constructive for the further design, modification and screening of drug molecules. Docking investigation demonstrated a non-covalent binding of 5d with CYP51 through hydrogen bond and hydrophobicity. These results strongly suggested that compound 5d could act as a potential template for the development of promising antifungal drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.022
• 作为产物：
  描述：

  2,3',4'-三氯苯乙酮 在 potassium carbonate 、 sodium hydroxide 作用下， 以 甲苯 、 乙腈 为溶剂， 生成 1-[[2-(3,4-Dichlorophenyl)oxiran-2-yl]methyl]-1,2,4-triazole
  参考文献：
  名称：

  克林沙星三唑杂种作为新型抗菌和抗真菌剂的设计，合成和评价

  摘要：

  首次合成了一系列作为新型抗菌剂和抗菌剂的克林沙星三唑杂种，并通过两次连续稀释技术筛选了对四种革兰氏阳性菌，四种革兰氏阴性菌和两种真菌的抗菌效果。生物活性测定表明，大多数靶标化合物对所有被测菌株均表现出宽广的抗菌谱以及良好的抗菌和抗真菌活性，MIC值范围从0.25至2μg/ mL，与参考药物相比具有可比甚至更好的功效。氯霉素，克林沙星和氟康唑。值得注意的是，一些合成的克林沙星三唑对耐甲氧西林的金黄色葡萄球菌显示出更强的功效 比他们的父母克林沙星。

  DOI：

  10.1016/j.bmcl.2012.07.064

文献信息

• Design, synthesis and evaluation of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents
  作者：Yan Wang、Guri L.V. Damu、Jing-Song Lv、Rong-Xia Geng、Da-Cheng Yang、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2012.07.064

  日期：2012.9

  A series of clinafloxacin triazole hybrids as a new type of antibacterial and antifungal agents were synthesized for the first time and screened for their antimicrobial efficacy against four Gram-positive bacteria, four Gram-negative bacteria and two fungi by two fold serial dilution technique. The bioactive assay indicated that most of the target compounds displayed broad antimicrobial spectrum and

  首次合成了一系列作为新型抗菌剂和抗菌剂的克林沙星三唑杂种，并通过两次连续稀释技术筛选了对四种革兰氏阳性菌，四种革兰氏阴性菌和两种真菌的抗菌效果。生物活性测定表明，大多数靶标化合物对所有被测菌株均表现出宽广的抗菌谱以及良好的抗菌和抗真菌活性，MIC值范围从0.25至2μg/ mL，与参考药物相比具有可比甚至更好的功效。氯霉素，克林沙星和氟康唑。值得注意的是，一些合成的克林沙星三唑对耐甲氧西林的金黄色葡萄球菌显示出更强的功效 比他们的父母克林沙星。
• Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungi
  作者：Yuan Zhang、Vijai Kumar Reddy Tangadanchu、Rammohan R. Yadav Bheemanaboina、Yu Cheng、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2018.06.022

  日期：2018.7

  A series of carbazole-triazole conjugates were designed, synthesized and characterized by IR, NMR, and HRMS spectra. Biological assay showed that most of the synthesized compounds exhibited moderate and even strong antifungal activities, especially 3,6-dibromocarbazolyl triazole 5d displayed excellent inhibitory efficacy against most of the tested fungal strains (MIC = 2-32 mu g/mL) and effectively fungicidal ability towards C albicans, C tropicals and C. parapsilosis ATCC 22019 (MFC = 4-8 mu g/mL). Its combination use with fluconazole could enhance the antifungal efficacy, and compound 5d also did not obviously trigger the development of resistance in C. albicans even after 10 passages. Preliminary mechanism study revealed that the active molecule 5d could depolarize fungal membrane potential and intercalate into DNA to possibly block DNA replication, thus possibly exhibiting its powerful antifungal abilities. Conjugate 5d could interact with HSA, which was constructive for the further design, modification and screening of drug molecules. Docking investigation demonstrated a non-covalent binding of 5d with CYP51 through hydrogen bond and hydrophobicity. These results strongly suggested that compound 5d could act as a potential template for the development of promising antifungal drugs. (C) 2018 Elsevier Masson SAS. All rights reserved.