N-(1-butyl-2-methyl-1H-benzo[d]imidazol-5-yl)amine | 912763-63-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-(1-butyl-2-methyl-1H-benzo[d]imidazol-5-yl)amine
• 英文别名: 1-Butyl-2-methyl-1H-benzimidazol-5-amine；1-butyl-2-methylbenzimidazol-5-amine
• CAS: 912763-63-4
• 化学式: C₁₂H₁₇N₃
• 分子量: 203.287
• InChiKey: SWEOVZYAORMRHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-butyl-2-methyl-1H-benzo[d]imidazol-5-yl)amine 以 乙醇 、 异丙醇 为溶剂， 反应 72.0h， 生成 N-(1-butyl-2-methyl-1H-benzo[d]imidazol-5-yl)-2(piperidin-1-yl)-9H-purin-6-amine
  参考文献：
  名称：

  Purine-benzimidazole hybrids: Synthesis, single crystal determination and in vitro evaluation of antitumor activities

  摘要：

  In an effort to identify novel compounds for the treatment of cancer, a diverse array of potential bioactive hybrid, purine-benzimidazole was synthesized in good yields through nucleophilic substitution at C6 position of purine ring with versatile cyclic amines at C2 position. The structures of newly prepared compounds were confirmed by IR, H-1, C-13 NMR, mass spectroscopy and, in case of 19, by single crystal Xray diffraction analysis. The newly synthesized compounds were evaluated against 60 human tumour cell lines at one dose concentration level. Compound 6 exhibited significant growth inhibition and was evaluated as 60 cell panel at five dose concentration levels. Compound 6 proved to be 1.25 fold more active than the positive control 5-FU, with GI(50) value of 18.12 mu M (MG-MID). Interaction of the compounds with Aurora-A enzyme involved in the process of propagation of cancer, has also been investigated. Compound 6 showed selectivity towards Aurora-A kinase inhibition with IC50 value of 0.01 mu M. Molecular docking studies in the active binding site provided theoretical support for the experimental biological data acquired. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.036
• 作为产物：
  描述：

  2-甲基-5-硝基苯并咪唑 在 盐酸 、 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 生成 N-(1-butyl-2-methyl-1H-benzo[d]imidazol-5-yl)amine
  参考文献：
  名称：

  Purine-benzimidazole hybrids: Synthesis, single crystal determination and in vitro evaluation of antitumor activities

  摘要：

  In an effort to identify novel compounds for the treatment of cancer, a diverse array of potential bioactive hybrid, purine-benzimidazole was synthesized in good yields through nucleophilic substitution at C6 position of purine ring with versatile cyclic amines at C2 position. The structures of newly prepared compounds were confirmed by IR, H-1, C-13 NMR, mass spectroscopy and, in case of 19, by single crystal Xray diffraction analysis. The newly synthesized compounds were evaluated against 60 human tumour cell lines at one dose concentration level. Compound 6 exhibited significant growth inhibition and was evaluated as 60 cell panel at five dose concentration levels. Compound 6 proved to be 1.25 fold more active than the positive control 5-FU, with GI(50) value of 18.12 mu M (MG-MID). Interaction of the compounds with Aurora-A enzyme involved in the process of propagation of cancer, has also been investigated. Compound 6 showed selectivity towards Aurora-A kinase inhibition with IC50 value of 0.01 mu M. Molecular docking studies in the active binding site provided theoretical support for the experimental biological data acquired. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.02.036

文献信息

• Compound
  申请人：——

  公开号：US20040143124A1

  公开（公告）日：2004-07-22

  A compound having Formula I 1 wherein one of R 1 and R 2 is a group of the formula 2 wherein R 4 is selected from H and hydrocarbyl, R 5 is a hydrocarbyl group and L is an optional linker group, or R 1 and R 2 together form a ring substituted with the group 3 wherein R 3 is H or a substituent, and wherein X is selected from S, O, NR 6 and C(R 7 )(R 8 ), wherein R 6 is selected from H and hydrocarbyl groups, wherein each of R 7 and R 8 are independently selected from H and hydrocarbyl groups.

  化合物具有I1式，其中R1和R2中的一个是公式2的基团，其中R4从H和烃基中选择，R5是烃基团，L是可选的连接基团，或者R1和R2一起形成带有基团3的环，其中R3是H或取代基，X从S，O，NR6和C（R7）（R8）中选择，其中R6从H和烃基团中选择，R7和R8各自独立地从H和烃基团中选择。
• US7309715B2
  申请人：——

  公开号：US7309715B2

  公开（公告）日：2007-12-18
• Purine-benzimidazole hybrids: Synthesis, single crystal determination and in vitro evaluation of antitumor activities
  作者：Alka Sharma、Vijay Luxami、Kamaldeep Paul

  DOI：10.1016/j.ejmech.2015.02.036

  日期：2015.3

  In an effort to identify novel compounds for the treatment of cancer, a diverse array of potential bioactive hybrid, purine-benzimidazole was synthesized in good yields through nucleophilic substitution at C6 position of purine ring with versatile cyclic amines at C2 position. The structures of newly prepared compounds were confirmed by IR, H-1, C-13 NMR, mass spectroscopy and, in case of 19, by single crystal Xray diffraction analysis. The newly synthesized compounds were evaluated against 60 human tumour cell lines at one dose concentration level. Compound 6 exhibited significant growth inhibition and was evaluated as 60 cell panel at five dose concentration levels. Compound 6 proved to be 1.25 fold more active than the positive control 5-FU, with GI(50) value of 18.12 mu M (MG-MID). Interaction of the compounds with Aurora-A enzyme involved in the process of propagation of cancer, has also been investigated. Compound 6 showed selectivity towards Aurora-A kinase inhibition with IC50 value of 0.01 mu M. Molecular docking studies in the active binding site provided theoretical support for the experimental biological data acquired. (C) 2015 Elsevier Masson SAS. All rights reserved.