N-phenyl-1H-benzo[d]imidazol-1-amine | 313485-89-1

• 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-phenyl-1H-benzo[d]imidazol-1-amine
• 英文别名: 1-phenylaminobenzimidazole；benzimidazol-1-yl-phenyl-amine；Benzimidazol-1-yl-phenyl-amin；N-phenylbenzimidazol-1-amine
• CAS: 313485-89-1
• 化学式: C₁₃H₁₁N₃
• 分子量: 209.25
• InChiKey: XNKGHTVZYQSHST-UHFFFAOYSA-N

物化性质

• 沸点：
  380.3±25.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-1H-benzo[d]imidazol-1-amine 在 吡啶 作用下， 以 甲醇 为溶剂， 反应 106.0h， 生成 1-(N-acetyl-N-phenylamino)-3-methylbenzimidazolium iodide
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724
• 作为产物：
  描述：

  2-苯基偶氮苯甲酰苯胺 在 盐酸 、 氢氧化钾 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-phenyl-1H-benzo[d]imidazol-1-amine
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724

文献信息

• NAPHTHALENE-BASED INHIBITORS OF ANTI-APOPTOTIC PROTEINS
  申请人：Pellecchia Maurizio

  公开号：US20090105319A1

  公开（公告）日：2009-04-23

  Methods of using apogossypol and its derivatives for treating inflammation is disclosed. Also, there is described a group of compounds having structure A, or a pharmaceutically acceptable salt, hydrate, N-oxide, or solvate thereof are provided: wherein each R is independently selected from the group consisting of H, C(O)X, C(O)NHX, NH(CO)X, SO 2 NHX, and NHSO 2 X, wherein X is selected from the group consisting of an alkyl, a substituted alkyl, an aryl, a substituted aryl, an alkylaryl, and a heterocycle. Compounds of group A may be used for treating various diseases or disorders, such as cancer.

  使用阿波戈司宝及其衍生物治疗炎症的方法被披露。此外，还描述了一组具有结构A的化合物，或其药学上可接受的盐、水合物、N-氧化物或溶剂化合物： 其中每个R独立地选自H、C(O)X、C(O)NHX、NH(CO)X、SO2NHX和NHSO2X组成的组，其中X选自烷基、取代烷基、芳基、取代芳基、烷基芳基和杂环的组。A组化合物可用于治疗各种疾病或疾病，如癌症。
• BICYCLIC ACETYL-COA CARBOXYLASE INHIBITORS AND USES THEREOF
  申请人：BARNES David Weninger

  公开号：US20120028969A1

  公开（公告）日：2012-02-02

  The present invention provides compounds of formula (I); or pharmaceutically acceptable salts thereof, wherein the variables are defined as herein. The present invention provides a method for manufacturing the compounds of formula (I), their therapeutic uses, combinations with other of pharmacologically active agents, and a pharmaceutical compositions.

  本发明提供了式(I)的化合物；或其药学上可接受的盐，其中变量如本文所定义。本发明提供了一种制造式(I)化合物的方法，它们的治疗用途，与其他药理活性剂的组合，以及药物组成。
• Site-Selective C-H Amidation of Azobenzenes with Dioxazolones under Rhodium Catalysis
  作者：Neeraj Kumar Mishra、Yongguk Oh、Mijin Jeon、Sangil Han、Satyasheel Sharma、Sang Hoon Han、Sung Hee Um、In Su Kim

  DOI：10.1002/ejoc.201601096

  日期：2016.10

  The rhodium(III)-catalyzed amidation reaction of azobenzenes with dioxazolones is described. This strategy allows the facile and efficient construction of highly substituted ortho-amidated azobenzenes via direct C-H cleavage approach. A range of substrate scope, excellent levels of chemoselectivity as well as high functional group tolerance were observed. In addition, this protocol was used to generate

  描述了铑 (III) 催化的偶氮苯与二恶唑酮的酰胺化反应。该策略允许通过直接 CH 裂解方法轻松有效地构建高度取代的邻位酰胺化偶氮苯。观察到一系列底物范围、优异的化学选择性以及高官能团耐受性。此外，该协议还用于生成一系列邻酰胺化酮。酰胺化偶氮苯的进一步合成转化为苯并咪唑和苯并三唑衍生物的构建提供了便利。
• Nucleic acid labeling compounds
  申请人：McGall H. Glenn

  公开号：US20050003496A1

  公开（公告）日：2005-01-06

  Nucleic acid labeling compounds containing heterocyclic derivatives are disclosed. Methods for making such heterocyclic compounds are also disclosed. The labeling compounds are suitable for enzymatic attachment to a nucleic acid, either terminally or internally, to provide a mechanism of nucleic acid detection.

  揭示了含有杂环衍生物的核酸标记化合物。还公开了制备这种杂环化合物的方法。这些标记化合物适用于通过酶的附着，无论是末端还是内部，提供核酸检测的机制。
• Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine
  作者：Hepan Wang、Song Sun、Jiang Cheng

  DOI：10.1016/j.tetlet.2017.08.066

  日期：2017.10

  A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “CH” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

  开发了钯催化的2-（芳基二氮烯基）苯胺和二甲基亚砜的环化反应，以中等至良好的产率获得N-芳基-1 H-苯并[ d ]咪唑-1-胺。DMSO被1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫）加合物（DABSO）激活，在此过程中充当“ CH ”片段。它代表了导致苯并咪唑的简便途径。