4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo[d]imidazol-2-yl]phenol | 154713-23-2

• 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: 4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo[d]imidazol-2-yl]phenol
• 英文别名: 4-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenol
• CAS: 154713-23-2
• 化学式: C₁₈H₂₀N₄O
• 分子量: 308.383
• InChiKey: KJHNXBVXVRECOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo[d]imidazol-2-yl]phenol 在 potassium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 (2S)-N-{5-(4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo[d]imidazol-2-yl]phenoxy)pentyloxy-5-methoxy-2-aminobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
  参考文献：
  名称：

  Synthesis of C8-linked pyrrolo[2,1-c][1,4]benzodiazepine–benzimidazole conjugates with remarkable DNA-binding affinity

  摘要：

  Two types of benzimidazoles have been synthesized and linked to DC-81 at C8-position through different alkyl chain spacers. These PBD conjugates have exhibited remarkable DNA-binding affinity, and a representative compound shows promising in vitro anticancer activity. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.06.069
• 作为产物：
  描述：

  2-硝基-5-氯苯胺 在 palladium on activated charcoal sodium metabisulfite 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-[6-(4-methylhexahydro-1-pyrazinyl)-1H-benzo[d]imidazol-2-yl]phenol
  参考文献：
  名称：

  Synthesis of C8-linked pyrrolo[2,1-c][1,4]benzodiazepine–benzimidazole conjugates with remarkable DNA-binding affinity

  摘要：

  Two types of benzimidazoles have been synthesized and linked to DC-81 at C8-position through different alkyl chain spacers. These PBD conjugates have exhibited remarkable DNA-binding affinity, and a representative compound shows promising in vitro anticancer activity. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.06.069

文献信息

• Synthetic Utility of Catalytic Fe(III)/Fe(II) Redox Cycling Towards Fused Heterocycles: A Facile Access to Substituted Benzimidazole, Bisbenzimidazole and Imidazopyridine Derivatives
  作者：Malvinder P. Singh、Sanjita Sasmal、Wei Lu、Manashi N. Chatterjee

  DOI：10.1055/s-2000-7111

  日期：——

  A catalytic Fe(III)/Fe(II) redox cycling approach has been examined and applied towards synthesis of a wide range of benzimidazole, bis-benzimidazole and imidazopyridine derivatives from oxidative coupling of aromatic ortho-diamines with aromatic as well as heterocyclic aldehydes bearing different types of substituents. This versatile and convenient method has further proven to be particularly useful

  已经研究了催化 Fe(III)/Fe(II) 氧化还原循环方法，并将其应用于通过芳香邻二胺与芳香醛和杂环醛的氧化偶联来合成各种苯并咪唑、双苯并咪唑和咪唑并吡啶衍生物不同类型的取代基。进一步证明，这种通用且方便的方法特别适用于迅速提供许多新型双苯并咪唑类 Hoechst 33 258 类似物，以作为荧光核酸结合探针的潜在开发。这里介绍了三十种不同化合物的成功制备和表征。
• [EN] PROCESS FOR PREPARING PYRROLO[2, 1-c] [1, 4] BENZODIAZEPINE HYBRIDS<br/>[FR] PROCEDE SERVANT A PREPARER DES HYBRIDES DE PYRROLO[2, 1-C] [1, 4] BENZODIAZEPINE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2005063759A1

  公开（公告）日：2005-07-14

  Novel pyrrolo[2, 1-c] [1, 4] benzodiazepine hybrids as well as processes for the proepartion of novel pyrrolo [2, 1-c] [1, 4] benzodiazepine hybrids are disclosed. More particularly, present invention relates to a process for the preparation of novel pyrrolo [2, 1-c] [1, 4] benzodiazepine hybrids as DNA sequence selective agents which are useful as potential antitumour agents. In particular, the present invention relates to a process for the preparation of new pyrrolo [2, 1-c] [1, 4] benzodiazepine hybrids as potential antitumour agents. These compounds have the formula (XIV).

  揭示了新型吡咯并[2,1-c][1,4]苯二氮䓬杂合物以及制备新型吡咯并[2,1-c][1,4]苯二氮䓬杂合物的方法。更具体地说，本发明涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮䓬杂合物的方法，作为DNA序列选择性剂，可用作潜在的抗肿瘤剂。特别是，本发明涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮䓬杂合物作为潜在抗肿瘤剂的方法。这些化合物的化学式为（XIV）。
• PROCESS FOR PREPARING PYRROLO[2, 1-C] [1,4] BENZODIAZEPINE HYBRIDS
  申请人：Kamal Ahmed

  公开号：US20050222133A1

  公开（公告）日：2005-10-06

  Novel pyrrolo[2,1-c][1,4]benzodiazepine hybrids as well as processes for the preparation of novel pyrrolo[2,1-c][1,4]benzodiazepine hybrids are dislcosed. More particularly, present invention relates to a process for the preparation of novel pyrrolo[2,1-c][1,4]benzodiazepine hybrids as DNA sequence selective agents which are useful as potential antitumour agents. In particular, the present invention relates to a process for the preparation of new pyrrolo [2,1-c][1,4]benzodiazepine hybrids as potential antitumour agents. These compounds have the formula XIV shown below:

  揭示了新型吡咯并[2,1-c][1,4]苯二氮杂环己烷杂合物以及制备新型吡咯并[2,1-c][1,4]苯二氮杂环己烷杂合物的方法。更具体地，本发明涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮杂环己烷杂合物的方法，这些杂合物作为DNA序列选择性试剂，可用作潜在的抗肿瘤剂。特别是，本发明涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮杂环己烷杂合物作为潜在抗肿瘤剂的方法。这些化合物的化学式如下所示：
• Synthesis of C8-linked pyrrolo[2,1-c][1,4]benzodiazepine–benzimidazole conjugates with remarkable DNA-binding affinity
  作者：Ahmed Kamal、P. Ramulu、O. Srinivas、G. Ramesh、P. Praveen Kumar

  DOI：10.1016/j.bmcl.2004.06.069

  日期：2004.9

  Two types of benzimidazoles have been synthesized and linked to DC-81 at C8-position through different alkyl chain spacers. These PBD conjugates have exhibited remarkable DNA-binding affinity, and a representative compound shows promising in vitro anticancer activity. (C) 2004 Published by Elsevier Ltd.