2-(4-chlorobenzylamino)benzimidazole | 679394-79-7

• 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: 2-(4-chlorobenzylamino)benzimidazole
• 英文别名: (1H-benzoimidazol-2-yl)-(4-chlorobenzyl)amine；N-[(4-chlorophenyl)methyl]-1H-benzimidazol-2-amine
• CAS: 679394-79-7
• 化学式: C₁₄H₁₂ClN₃
• mdl: MFCD09439049
• 分子量: 257.722
• InChiKey: GNCUDHLBPMQNEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  肉桂酰氯 、 2-(4-chlorobenzylamino)benzimidazole 以 四氢呋喃 为溶剂， 反应 40.0h， 以52%的产率得到
  参考文献：
  名称：

  Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives

  摘要：

  A novel series of Schiff bases 1-11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1-11 reduced by NaBH(4) formed 2-benzylaminobenzimidazoles 12-21. 2-(o-Bromobenzylamino)benzimidazole (15) acylated by cinnamoyl chloride gave 2-(o-bromobenzylamino)-1-cinnamoylbenzimidazole (22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1-24 were identified by the results of elemental analysis and their IR, (1)H NMR and MS spectra. Among the compounds 1-24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).

  DOI：

  10.1016/j.farmac.2003.12.001
• 作为产物：
  描述：

  2-(p-chlorobenzylideneamino)benzimidazole 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 4.0h， 以78%的产率得到2-(4-chlorobenzylamino)benzimidazole
  参考文献：
  名称：

  2-氨基苯并咪唑衍生物及其合成和应用

  摘要：

  本发明涉及一种化合物，具体涉及一种2‑氨基苯并咪唑衍生物及其合成工艺，其具有杀菌活性。2‑氨基苯并咪唑衍生物，其结构式I为：其中R为F、Cl、Br、OH或CH3；制备方法包括有以下步骤：S1)以2‑氨基苯并咪唑为起始原料在催化剂作用下经与取代芳香醛在反应溶剂存在下反应得到中间体N‑苯并咪唑基‑取代苯基亚胺，S2)N‑苯并咪唑基‑取代苯基亚胺经还原得到2‑取代苄基苯并咪唑。本发明的有益效果在于：本发明合成2‑氨基苯并咪唑衍生物工艺简单，结构新颖，采用菌丝生长速率法测定目标化合物对病原菌菌丝的生长抑制作用，发现部分化合物具有较高的杀菌活性，具有较大的发展潜力。

  公开号：

  CN110256359A

文献信息

• 2-氨基苯并咪唑衍生物及其合成和应用
  申请人：武汉工程大学

  公开号：CN110256359A

  公开（公告）日：2019-09-20

  本发明涉及一种化合物，具体涉及一种2‑氨基苯并咪唑衍生物及其合成工艺，其具有杀菌活性。2‑氨基苯并咪唑衍生物，其结构式I为：其中R为F、Cl、Br、OH或CH3；制备方法包括有以下步骤：S1)以2‑氨基苯并咪唑为起始原料在催化剂作用下经与取代芳香醛在反应溶剂存在下反应得到中间体N‑苯并咪唑基‑取代苯基亚胺，S2)N‑苯并咪唑基‑取代苯基亚胺经还原得到2‑取代苄基苯并咪唑。本发明的有益效果在于：本发明合成2‑氨基苯并咪唑衍生物工艺简单，结构新颖，采用菌丝生长速率法测定目标化合物对病原菌菌丝的生长抑制作用，发现部分化合物具有较高的杀菌活性，具有较大的发展潜力。
• Synthesis and Structure−Activity Relationship Studies of 2-(N-Substituted)-aminobenzimidazoles as Potent Negative Gating Modulators of Small Conductance Ca²⁺-Activated K⁺ Channels
  作者：Ulrik S. Sørensen、Dorte Strøbæk、Palle Christophersen、Charlotte Hougaard、Marianne L. Jensen、Elsebet Ø. Nielsen、Dan Peters、Lene Teuber

  DOI：10.1021/jm800809f

  日期：2008.12.11

  Small conductance Ca2+-activated K+ channels (SK channels) participate in the control of neuronal excitability, in the shaping of action potential firing patterns, and in the regulation of synaptic transmission. SK channel inhibitors have the potential of becoming new drugs for treatment of various psychiatric and neurological diseases such as depression, cognition impairment, and Parkinson's disease. In the present study we describe the structure-activity relationship (SAR) of a class of 2-(N-substituted)-2-aminobenzimidazoles that constitute a novel class of selective SK channel inhibitors that, in contrast to classical SK inhibitors, do not block the pore of the channel. The pore blocker apamin is not displaced by these compounds in binding studies, and they still inhibit SK channels in which the apamin binding site has been abolished by point mutations. These novel SK inhibitors shift the concentration-response curve for Ca2+ toward higher values and represent the first example of negative gating modulation as a mode-of-action for inhibition of SK channels. The first described compound in this class is NS8593 (14), and the most potent analogue identified in this study is the racemic compound 39 (NS11757), which reversibly inhibits SK3-rnediated currents with a K-d value of 9 nM.
• Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives
  作者：Wanda Nawrocka、Barbara Sztuba、Maria W Kowalska、Hanna Liszkiewicz、Joanna Wietrzyk、Anna Nasulewicz、Marzena Pełczyńska、Adam Opolski

  DOI：10.1016/j.farmac.2003.12.001

  日期：2004.2

  A novel series of Schiff bases 1-11, the derivatives of 2-aminobenzimidazole and substituted aromatic aldehydes, has been synthesised. Compounds 1-11 reduced by NaBH(4) formed 2-benzylaminobenzimidazoles 12-21. 2-(o-Bromobenzylamino)benzimidazole (15) acylated by cinnamoyl chloride gave 2-(o-bromobenzylamino)-1-cinnamoylbenzimidazole (22). Long heating of 15 and 19 with p-nitrocinnamoyl or cinnamoyl chloride led to the formation of pyrimido[1,2-a]benzimidazol-4-ones 23 and 24. The structures of 1-24 were identified by the results of elemental analysis and their IR, (1)H NMR and MS spectra. Among the compounds 1-24 evaluated for their antiproliferative activity in vitro, 16, 19, 20 and 22 exhibited cytotoxic activity against the cells of human cancer cell lines, namely SW707 (rectal), HCV29T (bladder), A549 (lung) and T47D (breast cancer).
• Nowicka, Anna; Nawrocka, Wanda P.; Liszkiewicz, Hanna, Acta poloniae pharmaceutica, 2018, vol. 75, # 2, p. 397 - 405
  作者：Nowicka, Anna、Nawrocka, Wanda P.、Liszkiewicz, Hanna、Wietrzyk, Joanna、Anisiewicz, Artur、Ko£Odziejczyk, Wojciech

  DOI：——

  日期：——