1-(N-cyclohexanemethylcarbamoyl)benzotriazole | 1377411-11-4

• 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-cyclohexanemethylcarbamoyl)benzotriazole
• 英文别名: N-(cyclohexylmethyl)benzotriazole-1-carboxamide
• CAS: 1377411-11-4
• 化学式: C₁₄H₁₈N₄O
• 分子量: 258.323
• InChiKey: MTLGPAKWJPKDGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-(3-phenoxyphenyl)propanehydrazide 、 1-(N-cyclohexanemethylcarbamoyl)benzotriazole 在 三乙胺 作用下， 反应 0.25h， 以50%的产率得到4-cyclohexanemethyl-1-[2-(3-phenoxyphenyl)propanoyl]semicarbazide
  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：

  环己甲胺 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 1-(N-cyclohexanemethylcarbamoyl)benzotriazole
  参考文献：
  名称：

  N-芳基脲衍生物对分枝杆菌和分枝杆菌水解酶的生化和微生物学评估。

  摘要：

  制备了聚焦的24种N-芳基脲衍生物文库，并针对结核分枝杆菌（Mtb）Rv3802c和Mtb Ag85C的丝氨酸酯酶进行了评估。对文库成员的选择性和抑制方式进行了评估。发现呋喃基尿素衍生物6c是Rv3802c最有效的非共价抑制剂，K i值为5.2±0.7μM。另一方面，基于三唑的脲10a和10b不可逆地选择性地抑制Ag85C，其ak inact / K i值分别为2.3±0.3和5.5±0.4×10-3μM-1min-1。还评估了文库对两种Mtb菌株（耻垢分枝杆菌和脓肿分枝杆菌）的最低抑制浓度（MIC）。化合物4a和4c具有抗Mtb H37Rv mc26206的活性，MIC值分别为3.12和1.5μM。密切相关的4e对Mtb H37Rv mc26206具有相似的活性，但对Mtb H37Ra，耻垢分枝杆菌和脓肿分枝杆菌也具有活性。化合物4a，4c和4e均包含一个共同的1-（环己基甲基）-3-苯

  DOI：

  10.1039/c9md00122k