2-(3,4-diaminophenyl)-1H-benzimidazole-5-carboxamidine | 752961-80-1

• 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: 2-(3,4-diaminophenyl)-1H-benzimidazole-5-carboxamidine
• 英文别名: 2-(3,4-diaminophenyl)-3H-benzimidazole-5-carboximidamide
• CAS: 752961-80-1
• 化学式: C₁₄H₁₄N₆
• 分子量: 266.305
• InChiKey: XCAWCVNHJBXIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 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：
  131
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-双三氟甲基苯甲醛 、 2-(3,4-diaminophenyl)-1H-benzimidazole-5-carboxamidine 在 sodium metabisulfite 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-[2-[3,5-bis(trifluoromethyl)phenyl]-3H-benzimidazol-5-yl]-3H-benzimidazole-5-carboximidamide
  参考文献：
  名称：

  合成和2'-芳基取代-1抗寄生虫和抗真菌评价ħ，1' ħ - [2,5'] bisbenzimidazolyl -5-甲脒

  摘要：

  一系列2'-芳基取代-1 ħ，1' ħ - [2,5'] - bisbenzimidazolyl -5-甲脒在由4-氨基-3-硝基苄腈开始的6步骤的过程中制备。在体外评价了对布鲁氏锥虫（Tbr），恶性疟原虫（Pf），利什曼原虫多诺尼（Ld）和克鲁氏锥虫（Tc）的抗寄生虫活性以及对白色念珠菌和库氏假丝酵母的抗真菌活性。几种化合物显示出对Tbr和Pf的体外活性与白色念珠菌相比，其对Pf的活性优于氯喹。

  DOI：

  10.1016/j.ejmech.2008.10.003
• 作为产物：
  描述：

  3,4-二氨基苯甲脒 在 palladium on activated charcoal 盐酸 、 氢气 、 对苯醌 作用下， 以 乙醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 6.5h， 生成 2-(3,4-diaminophenyl)-1H-benzimidazole-5-carboxamidine
  参考文献：
  名称：

  Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections

  摘要：

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.

  DOI：

  10.1021/jm9507946

文献信息

• [EN] TREATMENT OF ACANTHAMOEBA OR BALAMUTHIA TROPHOZOITES AND/OR CYSTS<br/>[FR] TRAITEMENT DE TROPHOZOÏTES ET/OU DE KYSTES D'ACANTHAMOEBA OU DE BALAMUTHIA
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2020081829A1

  公开（公告）日：2020-04-23

  Compounds, compositions, and methods for the treatment of infections caused by Acanthamoeba or Balamuthia mandnllaris trophozoites and/or cysts and for the disinfection of solids and/or liquids, such as medical and personal care items, for example contact lenses, that may harbor Acanthamoeba trophozoites and/or cysts are provided.

  提供了用于治疗由刺阿米巴或巴拉姆菲亚曼德纳里斯滋养体和/或囊虫引起的感染以及用于消毒固体和/或液体的化合物、组合物和方法，例如医疗和个人护理用品，例如隐形眼镜，可能藏有刺阿米巴滋养体和/或囊虫。
• TREATMENT OF ACANTHAMOEBA OR BALAMUTHIA TROPHOZOITES AND/OR CYSTS
  申请人：GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.

  公开号：US20220096441A1

  公开（公告）日：2022-03-31

  Compounds, compositions, and methods for the treatment of infections caused by Acanthamoeba or Balamuthia mandrillaris trophozoites and/or cysts and for the disinfection of solids and/or liquids, such as medical and personal care items, for example contact lenses, that may harbor Acanthamoeba trophozoites and/or cysts are provided.
• Synthesis and antiparasitic and antifungal evaluation of 2′-arylsubstituted-1H,1′H-[2,5′]bisbenzimidazolyl-5-carboxamidines
  作者：Mehmet Alp、Hakan Göker、Reto Brun、Sulhiye Yıldız

  DOI：10.1016/j.ejmech.2008.10.003

  日期：2009.5

  A series of 2′-arylsubstituted-1H,1′H-[2,5′]-bisbenzimidazolyl-5-carboxamidines were prepared in a six-step process starting from 4-amino-3-nitrobenzonitrile. The antiparasitic activity against Trypanosoma brucei rhodesiense (T.b.r.), Plasmodium falciparum (P.f.), Leishmania donovani (L.d.) and Trypanosoma cruzi (T.c.) and antifungal activity against Candida albicans and Candida krusei were evaluated

  一系列2'-芳基取代-1 ħ，1' ħ - [2,5'] - bisbenzimidazolyl -5-甲脒在由4-氨基-3-硝基苄腈开始的6步骤的过程中制备。在体外评价了对布鲁氏锥虫（Tbr），恶性疟原虫（Pf），利什曼原虫多诺尼（Ld）和克鲁氏锥虫（Tc）的抗寄生虫活性以及对白色念珠菌和库氏假丝酵母的抗真菌活性。几种化合物显示出对Tbr和Pf的体外活性与白色念珠菌相比，其对Pf的活性优于氯喹。
• Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections
  作者：Richard L. Lombardy、Farial A. Tanious、Kishore Ramachandran、Richard R. Tidwell、W. David Wilson

  DOI：10.1021/jm9507946

  日期：1996.1.1

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.