3-amino-4-butylaminobenzonitrile | 143173-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-amino-4-butylaminobenzonitrile
• 英文别名: 3-Amino-4-(butylamino)benzonitrile
• CAS: 143173-92-6
• 化学式: C₁₁H₁₅N₃
• 分子量: 189.26
• InChiKey: RNCJOEPIGOZWEB-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±32.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4-butylaminobenzonitrile 在 sodium disulfite 、 二异丁基氢化铝 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 1-butyl-2-phenyl-1H-benzimidazol-5-carboxaldehyde
  参考文献：
  名称：

  Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species

  摘要：

  New 2-substituted-phenyl-1H-benzimidazole-5-carboxylic acids (35, 38), ethyl-5-carboxylate (36), -5-carboxamides (37, 39),-5-carboxaldeliyde (42), -5-chloro (40), -5-trifluoromethyl (41), and -5-carbonitriles (44-53, 55-67), -6-carbonitrilc (54) were prepared and evaluated in vitro against Candida species. The cyano substituted compounds 53, 57, 58 and 61 exhibited the greatest activity with MIC values of 3.12 mug/mL, values similar to that of fluconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00103-7
• 作为产物：
  描述：

  4-氯-3-硝基苯甲腈 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-amino-4-butylaminobenzonitrile
  参考文献：
  名称：

  RING CLEAVAGE OF DICYANO-SUBSTITUTED BENZIMIDAZOLES BY DIBAL

  摘要：

  DOI：

  10.1515/hc.2001.7.6.529

文献信息

• Synthesis and potent antifungal activity against<i>Candida</i>species of some novel 1<i>H</i>-benzimidazoles
  作者：Hakan Göker、Mehmet Alp、Zeynep Ateş-Alagöz、Sulhiye Yıldız

  DOI：10.1002/jhet.179

  日期：2009.9

  A series of 47 novel N1-alkylated-2-aryl-5(6)-substituted-1H-benzimidazoles and their three novel indole analogues were synthesized and evaluated for in vitro antifungal activities against Candida species by the tube dilution method. The results showed that compounds 79 and 80, having pyridine at the position C-2, of benzimidazoles exhibited the greatest activity with MIC values of 6.25–3.12 μg/mL

  合成了一系列47种新颖的N 1-烷基化-2-芳基-5（6）-取代的1 H-苯并咪唑及其三种新颖的吲哚类似物，并通过试管稀释法评估了其对念珠菌的体外抗真菌活性。结果表明，苯并咪唑类化合物在C-2位置具有吡啶的化合物79和80表现出最大的活性，MIC值为6.25–3.12μg/ mL。吲哚类似物108-110没有抑制活性。J.杂环化​​学，（2009）。
• Synthesis, potent anti-staphylococcal activity and QSARs of some novel 2-anilinobenzazoles
  作者：Seçkin Özden、Dilek Atabey、Sulhiye Yıldız、Hakan Göker

  DOI：10.1016/j.ejmech.2007.10.009

  日期：2008.7

  Synthesis and anti-staphylococcal activity of a number of substituted 2-anilinobenzimidazoles, benzothiazoles and benzoxazoles are reported. The anti-staphylococcal activities were evaluated in standard in vitro MIC assay method. While anilinobenzimidazole derivatives 11-45 showed very potent anti-staphylococcal activities (greatest activity with an MIC value of 0.095 mu g/mL), none of the 2-anilinobenzothiazoles and benzoxazole derivatives exhibited inhibitory activity. QSAR analysis of the anilinobenzimidazoles was studied on the relationship between the anti-staphylococcal activity (MIC in mu g/ml) and extrapolated log k(w) values. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Synthesis and<i>In Vitro</i>Activity of Polyhalogenated 2-phenylbenzimidazoles as a New Class of anti-MRSA and Anti-VRE Agents
  作者：Hakan Göker、Cigdem Karaaslan、Mustafa Orhan Püsküllü、Sulhiye Yildiz、Yalcin Duydu、Aylin Üstündağ、Can Özgür Yalcin

  DOI：10.1111/cbdd.12623

  日期：2016.1

  A series of novel polyhalogenated 2‐phenylbenzimidazoles have been synthesized and evaluated for in vitro antistaphylococcal activity against drug‐resistant bacterial strains (methicillin‐resistant Staphylococcus aureus, and vancomycin‐resistant Enterococcus faecium. Certain compounds inhibit bacterial growth perfectly. 11 was active than vancomycin (0.78 μg/mL) with the lowest MIC values with 0.19 μg/mL against methicillin‐resistant Staphylococcus aureus, 8 and 35 exhibited best inhibitory activity against vancomycin‐resistant Enterococcus faecium (1.56 μg/mL). The mechanism of action for this class of compounds appears to be different than clinically used antibiotics. These polyhalogenated benzimidazoles have potential for further investigation as a new class of potent anti‐methicillin‐resistant Staphylococcus aureus and anti‐vancomycin‐resistant Enterococcus faecium agents.
• RING CLEAVAGE OF DICYANO-SUBSTITUTED BENZIMIDAZOLES BY DIBAL
  作者：David W. Boykin、Hakan Göker

  DOI：10.1515/hc.2001.7.6.529

  日期：2001.1
• Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species
  作者：Hakan Göker、Canan Kuş、David W. Boykin、Sulhiye Yildiz、Nurten Altanlar

  DOI：10.1016/s0968-0896(02)00103-7

  日期：2002.8

  New 2-substituted-phenyl-1H-benzimidazole-5-carboxylic acids (35, 38), ethyl-5-carboxylate (36), -5-carboxamides (37, 39),-5-carboxaldeliyde (42), -5-chloro (40), -5-trifluoromethyl (41), and -5-carbonitriles (44-53, 55-67), -6-carbonitrilc (54) were prepared and evaluated in vitro against Candida species. The cyano substituted compounds 53, 57, 58 and 61 exhibited the greatest activity with MIC values of 3.12 mug/mL, values similar to that of fluconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.