1-acetyl-2-cyanomethylbenzimidazole

• 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: 1-acetyl-2-cyanomethylbenzimidazole
• 英文别名: 2-(1-acetyl-1H-benzo[d]imidazol-2(3H)-ylidene)acetonitrile；(1-acetyl-1H-benzimidazol-2-yl)acetonitrile；2-(1-acetylbenzimidazol-2-yl)acetonitrile
• 化学式: C₁₁H₉N₃O
• mdl: MFCD00652973
• 分子量: 199.212
• InChiKey: ZCBZMJCZOHBZDE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-2-cyanomethylbenzimidazole 以45%的产率得到
  参考文献：
  名称：

  VOLOVENKO, YU. M.;KUTROV, G. P.;SIDORENKO, V. N.;BABICHEV, F. S., DOKL. AN YCCP, 1983, N 10, 38-40

  摘要：

  DOI：
• 作为产物：
  描述：

  邻苯二胺 在 溶剂黄146 作用下， 反应 0.5h， 生成 1-acetyl-2-cyanomethylbenzimidazole
  参考文献：
  名称：

  New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole

  摘要：

  The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.

  DOI：

  10.17344/acsi.2015.1668

文献信息

• Imidazole derivatives containing potentially labile groups on the N(1) atom 8. Synthesis of N-aminoimidazoles via 1-amino-3-methoxymethylimidazolium and 1-amino-3-acetylimidazolium salts
  作者：O. V. Vinogradova、O. V. Kryshtalyuk、M. I. Rudnev、A. F. Pozharskii、V. V. Kuz'menko

  DOI：10.1007/bf01184881

  日期：1994.10
• New approaches for the synthesis, cytotoxicity and toxicity of heterocyclic compounds derived from 2-cyanomethyl benzo[c]imidazole
  作者：Rafat Mohareb、Abeer Mohamed、Amira Abdalla

  DOI：10.17344/acsi.2015.1668

  日期：2016.6.15

  The reaction of ethyl cyanoacetate with o-phenylenediamine gave the 2-cyanomethylbenzo[c]imidazole (1). The latter compound was used as the key starting material to synthesise biologically active heterocyclic derivatives. Thus, the reaction of 1 with cyclohexanone and either of benzaldehyde, 4-methoxybenzaldehyde or 4-chlorobenzaldehyde gave the annulated derivatives 2a-c, respectively. The antitumor evaluations of the newly synthesized products against the three cancer cell lines MCF-7 (breast adeno-carcinoma), NCI-H460 (non-small cell lung cancer) and SF-268 (CNS cancer) showed that compounds 2b, 6, 11b, 11c, 12b, 16a, 16b and 18a exhibited optimal cytotoxic effect against cancer cell lines, with IC50 values in the nM range. Bioactive compounds are often toxic to shrimp larvae. Thus, in order to monitor these chemicals in vivo lethality to shrimp larvae (Artemia salina), Brine-Shrimp Lethality Assay was used. Compounds 11b, 12b and 16b showed no toxicity against the tested organisms.
• VOLOVENKO, YU. M.;KUTROV, G. P.;SIDORENKO, V. N.;BABICHEV, F. S., DOKL. AN YCCP, 1983, N 10, 38-40
  作者：VOLOVENKO, YU. M.、KUTROV, G. P.、SIDORENKO, V. N.、BABICHEV, F. S.

  DOI：——

  日期：——