2-p-tolyl-5-cyanobenzimidazole | 174648-20-5

• 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-p-tolyl-5-cyanobenzimidazole
• 英文别名: 2-(p-tolyl)-1H-benzo[d]imidazole-5-carbonitrile；2-p-tolyl-1H-benzoimidazole-5-carbonitrile；2-(4-Methylphenyl)-1H-benzimidazole-6-carbonitrile；2-(4-methylphenyl)-3H-benzimidazole-5-carbonitrile
• CAS: 174648-20-5
• 化学式: C₁₅H₁₁N₃
• mdl: MFCD24862101
• 分子量: 233.272
• InChiKey: ZTQJHUADEZUOES-UHFFFAOYSA-N

物化性质

• 沸点：
  474.7±47.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-p-tolyl-5-cyanobenzimidazole 在 aluminum nickel sodium hydroxide 、 甲酸 、 双氧水 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 、 硝基苯 为溶剂， 反应 6.0h， 生成 2'-p-tolyl-5-(aminocarbonyl)-2,5'-bi-1H-benzimidazole
  参考文献：
  名称：

  Substituted 2,5‘-Bi-1H-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity

  摘要：

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.

  DOI：

  10.1021/jm950412w
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 硝基苯 为溶剂， 145.0 ℃ 、310.27 kPa 条件下， 反应 1.5h， 生成 2-p-tolyl-5-cyanobenzimidazole
  参考文献：
  名称：

  Substituted 2,5‘-Bi-1H-benzimidazoles:  Topoisomerase I Inhibition and Cytotoxicity

  摘要：

  Several 2'-aryl-5-substituted-2,5'-bi-1H-benzimidazole derivatives were synthesized and evaluated as topoisomerase I poisons and for their cytotoxicity toward the human lymphoblast cell line RPMI 8402. This study focused on 18 2,5'-bi-1H-benzimidazole derivatives which contained either a 5-cyano, a 5-(aminocarbonyl), or a 5-(4-methylpiperazinyl) group. Among these bibenximidazoles, the pharmacological activity of 2'-phenyl derivatives and the influence of the different positional isomers of either a 2'-tolyl group or a 2'-naphthyl moiety on cytotoxicity and topoisomerase I inhibitory activity were determined.

  DOI：

  10.1021/jm950412w

文献信息

• Substituted 2-Phenyl-benzimidazoles and their use as pharmaceuticals
  申请人：Sanofi-Aventis

  公开号：EP1905764A1

  公开（公告）日：2008-04-02

  The present invention relates to derivatives of 2-phenyl-benzimidazoles of the general formula (I), in which X, R, R1 to R3 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及通式(I)中2-苯基-苯并咪唑衍生物，其中X、R、R1至R3和n具有声明中所示的含义，这些衍生物调节内皮一氧化氮（NO）合酶的转录，并且是有价值的药理活性化合物。具体地，通式I的化合物上调内皮一氧化氮合酶酶的表达，并可应用于需要增加该酶的表达、增加NO水平或将降低的NO水平恢复正常的情况。该发明还涉及通式I化合物的制备方法，包括它们的药物组合物，以及将通式I化合物用于制造用于促进内皮一氧化氮合酶表达或治疗各种疾病的药物，包括心血管疾病如动脉粥样硬化、血栓形成、冠状动脉疾病、高血压和心脏功能不全等。
• Substituted 2-phenyl-benzimidazoles and their use as pharmaceuticals
  申请人：ZOLLER Gerhard

  公开号：US20090239915A1

  公开（公告）日：2009-09-24

  The present invention relates to derivatives of 2-phenyl-benzimidazoles of the formula I, in which X, R, R1 to R3 and n have the meanings indicated in the claims, which modulate the transcription of endothelial nitric oxide (NO) synthase and are valuable pharmacologically active compounds. Specifically, the compounds of the formula I upregulate the expression of the enzyme endothelial NO synthase and can be applied in conditions in which an increased expression of said enzyme or an increased NO level or the normalization of a decreased NO level is desired. The invention further relates to processes for the preparation of compounds of the formula I, to pharmaceutical compositions comprising them, and to the use of compounds of the formula I for the manufacture of a medicament for the stimulation of the expression of endothelial NO synthase or for the treatment of various diseases including cardiovascular disorders such as atherosclerosis, thrombosis, coronary artery disease, hypertension and cardiac insufficiency, for example.

  本发明涉及公式I的2-苯基苯并咪唑衍生物，其中X，R，R1至R3和n具有所述权利要求中所示的含义，其调节内皮型一氧化氮(NO)合酶的转录并具有药理活性。具体而言，公式I的化合物上调内皮型NO合酶的表达，并可应用于需要增加该酶的表达或增加NO水平或正常化降低的NO水平的情况。本发明还涉及制备公式I化合物的过程，包括它们的制药组合物，以及使用公式I化合物制备用于刺激内皮型NO合酶表达或治疗各种疾病的药物，包括心血管疾病，如动脉粥样硬化，血栓形成，冠状动脉疾病，高血压和心力衰竭等。
• [EN] C-MYC MRNA TRANSLATION MODULATORS AND USES THEREOF IN THE TREATMENT OF CANCER<br/>[FR] MODULATEURS DE TRADUCTION D'ARNM C-MYC ET LEURS UTILISATIONS DANS LE TRAITEMENT DU CANCER
  申请人：ANIMA BIOTECH INC

  公开号：WO2022150316A1

  公开（公告）日：2022-07-14

  The present invention relates to novel c-MYC mRNA translation modulators, composition and methods of preparation thereof, and uses thereof in the treatment of cancer.

  本发明涉及一种新型c-MYC mRNA翻译调节剂，其组成物和制备方法，以及在癌症治疗中的应用。
• SUBSTITUTED 2-PHENYL-BENZIMIDAZOLES AND THEIR USE AS PHARMACEUTICALS
  申请人：Sanofi-Aventis

  公开号：EP2079709B1

  公开（公告）日：2011-05-18
• C-MYC MRNA TRANSLATION MODULATORS AND USES THEREOF IN THE TREATMENT OF CANCER
  申请人：Anima Biotech Inc.

  公开号：US20220370431A1

  公开（公告）日：2022-11-24

  The present invention relates to novel c-MYC mRNA translation modulators, composition and methods of preparation thereof, and uses thereof in the treatment of cancer.