1-(N-2-phenylethylcarbamoyl)benzotriazole | 70243-22-0

• 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: 1-(N-2-phenylethylcarbamoyl)benzotriazole
• 英文别名: N-(2-phenylethyl)benzotriazole-1-carboxamide
• CAS: 70243-22-0
• 化学式: C₁₅H₁₄N₄O
• 分子量: 266.302
• InChiKey: OAFNAZYHCRKONH-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C(Solvent: Benzene)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(N-2-phenylethylcarbamoyl)benzotriazole 在 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 4-(2-phenylethyl)semicarbazide
  参考文献：
  名称：

  伯氨喹的新型1-酰基-4-取代的氨基脲衍生物-合成，细胞抑制，抗病毒和抗氧化研究。

  摘要：

  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。

  DOI：

  10.3109/14756366.2012.663366
• 作为产物：
  描述：

  T406石油添加剂 在 三乙胺 作用下， 生成 1-(N-2-phenylethylcarbamoyl)benzotriazole
  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

文献信息

• CARBAMOYLBENZOTRIAZOLE DERIVATIVES AS INHIBITORS OF LIPASES AND PHOSPHOLIPASES
  申请人：Petry Stefan

  公开号：US20080287503A1

  公开（公告）日：2008-11-20

  The invention relates to carbamoylbenzotriazole derivatives of general formula (I), which are defined as cited in the description, to their pharmaceutically applicable salts and to their use as medicaments.

  这项发明涉及一般式(I)的氨基甲酰基苯并三唑衍生物，其在描述中被定义，以及它们的药用盐和作为药物的用途。
• P(III)‐Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
  作者：Haiwen Meng、Kunhui Sun、Zhimin Xu、Lifang Tian、Yahui Wang

  DOI：10.1002/ejoc.202100113

  日期：2021.3.19

  P(III)‐assisted electrochemical generation of isocyanates from hydroxamic acids was successfully applied in the synthesis of ureas. Hydroxamic acids were directly used without pre‐activation, and the reaction was found not sensitive to water or air. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with trivalent phosphine to form corresponding alkoxyphosphoniums

  由异羟肟酸的P（III）辅助电化学生成异氰酸酯已成功应用于尿素的合成中。直接使用异羟肟酸而不进行预活化，发现该反应对水或空气不敏感。该方法开始于异羟肟酸的阳极氧化，然后与三价膦反应形成相应的烷氧基phosph，然后重排以得到异氰酸酯。
• 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：——
• CARBAMOYLBENZOTRIAZOL-DERIVATE ALS INHIBITOREN VON LIPASEN UND PHOSPHOLIPASEN
  申请人：SANOFI

  公开号：EP1940807B1

  公开（公告）日：2015-06-17
• US7897625B2
  申请人：——

  公开号：US7897625B2

  公开（公告）日：2011-03-01