N-benzyloxy-1H-benzotriazole-1-carboxamide | 301651-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-benzyloxy-1H-benzotriazole-1-carboxamide
• 英文别名: 1-(N-benzyloxycarbamoyl)benzotriazole；N-phenylmethoxybenzotriazole-1-carboxamide
• CAS: 301651-11-6
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: MGUXWCZZANELOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyloxy-1H-benzotriazole-1-carboxamide 在 一水合肼 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 生成 5-benzyloxycarbamoyl-1-[2-(4-isobutylphenyl)propanoyl]carbazide
  参考文献：
  名称：

  Novel NSAID 1-acyl-4-cycloalkyl/arylsemicarbazides and 1-acyl-5-benzyloxy/hydroxy carbamoylcarbazides as potential anticancer agents and antioxidants

  摘要：

  The novel 1-acyl-4-cycloalkyl/arylsemicarbazides (5a-y) and 1-acyl-5-benzyloxy/hydroxy carbamoylcarbazides (8a-f) derived from the nonsteroidal anti-inflammatory drugs ibuprofen, fenoprofen and reduced ketoprofen were prepared, fully chemically characterized and evaluated for their cytostatic, antiviral and antioxidant activities. Compounds 5 and 8 consist of a region rich in electronegative atoms (five to nine nitrogen and oxygen atoms) framed by aryl or cycloalkyl residues on one or both terminal ends. The synthetic pathways applied for the preparation of the title compounds involved a benzotriazole as a synthetic auxiliary in several steps. Three of the tested compounds, namely 4-benzhydryl-1-[2-(3-phenoxyphenyl)propanoyl]semicarbazide (5l), 4-benzhydryl-1-[2-(3-benzylphenyl)propanoyl]semicarbazide (5s), and 4-benzhydryl-1-[2-(4-isobutylphenyl)propanoyl]semicarbazide (5f) showed pronounced antiproliferative activity in vitro against six cancer cell lines (IC50 = 3-23 mu M). The same compounds highly inhibited soybean lipoxygenase (IC50 = 60 and 51.5 mu M) and lipid peroxidation as well (99, 88 and 74%, respectively). 4-Benzyloxy-1-[2-(4-isobutylphenyl)propanoyl]semicarbazide (5t) and 5-benzyloxycarbamoyl-1-[2-(3-benzylphenyl)propanoyl]carbazide (8c) exerted complete lipid peroxidation inhibition. Semicarbazides 5w-y and carbazides 8d-f bearing a hydroxamic acid/hydroxyurea moiety showed a modest antiradical activity in DPPH test, while the best radical scavenger was 1-(1-benzotriazolecarbonyl)-4-benzyloxysemicarbazide (7). None of the compounds were inhibitory to a broad panel of DNA and RNA viruses in the cell culture at subtoxic concentrations. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.046
• 作为产物：
  描述：

  苄氧基胺盐酸盐 、 苯并三唑-1-碳酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 N-benzyloxy-1H-benzotriazole-1-carboxamide
  参考文献：
  名称：

  Butula, Ivan; Takac, Milena Jadrijevic-Mladar, Croatica Chemica Acta, 2000, vol. 73, # 2, p. 569 - 574

  摘要：

  DOI：

文献信息

• Novel 1-acyl-4-substituted semicarbazide derivatives of primaquine − synthesis, cytostatic, antiviral and antioxidative studies
  作者：Ivana Perković、Sara Tršinar、Jelena Žanetić、Marijeta Kralj、Irena Martin-Kleiner、Jan Balzarini、Dimitra Hadjipavlou-Litina、Anna Maria Katsori、Branka Zorc

  DOI：10.3109/14756366.2012.663366

  日期：2013.6.1

  series of novel 1,4-substituted semicarbazides 5a-g with a primaquine moiety bridged by a carbonyl group at position 1 and a cycloalkyl, aryl, benzyloxy or hydroxy substituent at position 4 were prepared and biologically evaluated. The synthetic pathways applied for preparation of the title compounds involved benzotriazole as synthetic auxiliary. Primaquine semicarbazides 5a-g and their synthetic precursors

  制备一系列新颖的1，4-取代的氨基脲5a-g，其具有在位置1的羰基桥接的伯氨喹部分和在位置4的环烷基，芳基，苄氧基或羟基取代基，并进行了生物学评估。用于制备标题化合物的合成途径涉及苯并三唑作为合成助剂。评估了伯氨喹氨基脲5a-g及其合成前体苯并三唑羰基氨基脲4的抑制细胞生长，抗病毒和抗氧化活性。第5系列的所有化合物均对MCF-7细胞（乳腺癌）表现出高选择性，IC（50）值在低微摩尔范围内，而活性最高的是苄基衍生物5c（IC（50）1±0.2 µM）。苯甲酰基衍生物5e对所有测试的细胞系（IC（50）4-18 µM）均显示出显着的细胞抑制活性。同样的化合物也是最强的脂氧合酶抑制剂（51％）。羟基衍生物5g和苯并三唑羰基氨基脲4b，c（61.2-68.5％）的抗氧化剂活性最高。没有观察到针对多种DNA和RNA病毒的抗病毒活性。
• Butula, Ivan; Takac, Milena Jadrijevic-Mladar, Croatica Chemica Acta, 2000, vol. 73, # 2, p. 569 - 574
  作者：Butula, Ivan、Takac, Milena Jadrijevic-Mladar

  DOI：——

  日期：——
• Novel NSAID 1-acyl-4-cycloalkyl/arylsemicarbazides and 1-acyl-5-benzyloxy/hydroxy carbamoylcarbazides as potential anticancer agents and antioxidants
  作者：I. Perković、I. Butula、M. Kralj、I. Martin-Kleiner、J. Balzarini、D. Hadjipavlou-Litina、A.-M. Katsori、B. Zorc

  DOI：10.1016/j.ejmech.2012.02.046

  日期：2012.5

  The novel 1-acyl-4-cycloalkyl/arylsemicarbazides (5a-y) and 1-acyl-5-benzyloxy/hydroxy carbamoylcarbazides (8a-f) derived from the nonsteroidal anti-inflammatory drugs ibuprofen, fenoprofen and reduced ketoprofen were prepared, fully chemically characterized and evaluated for their cytostatic, antiviral and antioxidant activities. Compounds 5 and 8 consist of a region rich in electronegative atoms (five to nine nitrogen and oxygen atoms) framed by aryl or cycloalkyl residues on one or both terminal ends. The synthetic pathways applied for the preparation of the title compounds involved a benzotriazole as a synthetic auxiliary in several steps. Three of the tested compounds, namely 4-benzhydryl-1-[2-(3-phenoxyphenyl)propanoyl]semicarbazide (5l), 4-benzhydryl-1-[2-(3-benzylphenyl)propanoyl]semicarbazide (5s), and 4-benzhydryl-1-[2-(4-isobutylphenyl)propanoyl]semicarbazide (5f) showed pronounced antiproliferative activity in vitro against six cancer cell lines (IC50 = 3-23 mu M). The same compounds highly inhibited soybean lipoxygenase (IC50 = 60 and 51.5 mu M) and lipid peroxidation as well (99, 88 and 74%, respectively). 4-Benzyloxy-1-[2-(4-isobutylphenyl)propanoyl]semicarbazide (5t) and 5-benzyloxycarbamoyl-1-[2-(3-benzylphenyl)propanoyl]carbazide (8c) exerted complete lipid peroxidation inhibition. Semicarbazides 5w-y and carbazides 8d-f bearing a hydroxamic acid/hydroxyurea moiety showed a modest antiradical activity in DPPH test, while the best radical scavenger was 1-(1-benzotriazolecarbonyl)-4-benzyloxysemicarbazide (7). None of the compounds were inhibitory to a broad panel of DNA and RNA viruses in the cell culture at subtoxic concentrations. (C) 2012 Elsevier Masson SAS. All rights reserved.