1-(1-p-methoxyphenyl-1H-1,2,3-triazol-4-yl)ethanone | 88860-93-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1-p-methoxyphenyl-1H-1,2,3-triazol-4-yl)ethanone
• 英文别名: 1-(p-methoxyphenyl)-4-acetyltriazole；1-[1-(4-Methoxyphenyl)triazol-4-yl]ethanone
• CAS: 88860-93-9
• 化学式: C₁₁H₁₁N₃O₂
• 分子量: 217.227
• InChiKey: DPRXCAJOIAVWPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1-p-methoxyphenyl-1H-1,2,3-triazol-4-yl)ethanone 在 盐酸羟胺 、 溴 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(1-p-methoxyphenyl-1H-1,2,3-triazol-4-yl)-2-bromoethanone oxime
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052
• 作为产物：
  描述：

  1-叠氮基-4-甲氧基苯 在 sodium dichromate 、 copper(ll) sulfate pentahydrate 、 硫酸 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 1-(1-p-methoxyphenyl-1H-1,2,3-triazol-4-yl)ethanone
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052

文献信息

• Markova, N. K.; Tsil'ko, A. E.; Galishev, V. A., Journal of Organic Chemistry USSR (English Translation), 1983, p. 1990 - 1993
  作者：Markova, N. K.、Tsil'ko, A. E.、Galishev, V. A.、Maretina, I. A.

  DOI：——

  日期：——
• BENATI, LUISA;MONTEVECCHI, P. CARLO;SPAGNOLO, PIERO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N2, C. 2235-2243
  作者：BENATI, LUISA、MONTEVECCHI, P. CARLO、SPAGNOLO, PIERO

  DOI：——

  日期：——
• MARKOVA, N. K.;TSILKO, A. E.;GALISHEV, V. A.;MARETINA, I. A., ZH. ORGAN. XIMII, 1983, 19, N 11, 2281-2285
  作者：MARKOVA, N. K.、TSILKO, A. E.、GALISHEV, V. A.、MARETINA, I. A.

  DOI：——

  日期：——