4,4'-(1,4-piperazinediyl)bisbenzenecarboximidamide | 123885-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4,4'-(1,4-piperazinediyl)bisbenzenecarboximidamide
• 英文别名: 1.4-Bis-<4-amidino-phenyl>-piperazin；4,4'-piperazine-1,4-diyl-bis-benzamidine；4,4'-(piperazine-1,4-diyl)bis(benzenecarboximidamide)；4-[4-(4-Carbamimidoylphenyl)piperazin-1-yl]benzenecarboximidamide
• CAS: 123885-92-7
• 化学式: C₁₈H₂₂N₆
• 分子量: 322.413
• InChiKey: GFDIGDWACCJVOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4'-(1,4-piperazinediyl)bisbenzonitrile 在 盐酸 、 乙醇 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 97.0h， 生成 4,4'-(1,4-piperazinediyl)bisbenzenecarboximidamide
  参考文献：
  名称：

  Antitumor and Anti-Pneumocystis Carinii Activities of Novel Bisbenzamidines

  摘要：

  Among a library of 17 bisbenzamidines connected with various linkers, compounds with a flexible pentanediamide (10) or hexanediamide (12) linker were the most potent derivatives against rat Pneumocystis carinii (IC50 values of 3 and 2 nM, respectively) and had the highest selectivity index ratios (GI(50) of human tumor cells/IC50 of rat P. carinii cells) of > 10(4). Seven compounds caused 50% growth inhibition (GI(50)) of tumor cells at concentrations of < 100 mu M while the remaining ten were not cytotoxic. DNA binding affinity (Delta T-m) of the tested compounds did not correlate with either their anti-P. carinii activity or cytotoxicity.

  DOI：

  10.1007/s00044-005-0130-2

文献信息

• Bisbenzamidines and bisbenzamidoximes for the treatment of human African trypanosomiasis
  申请人：HUANG Tien L.

  公开号：US20080139534A1

  公开（公告）日：2008-06-12

  Disclosed are bisbenzamidine and bisbenzamidoxime compounds useful for treatment of treatment of trypanosomiasis. The compounds disclosed are useful for treating mammals infected with parasitic hemoflagellates, in particular Trypanosoma brucei gambiense and Trypanosoma brucei rhodesiense.

  揭示了对治疗锥虫病有用的双苯甲酰胺和双苯甲酰肟化合物。所揭示的化合物对治疗感染寄生性血液旗ellates的哺乳动物特别有效，尤其是对于甘比亚锥虫和罗德西亚锥虫。
• Bisbenzamidine derivatives for use as antioxidant
  申请人：Université de Mons-Hainaut

  公开号：EP2116236A1

  公开（公告）日：2009-11-11

  The invention is directed to the use of bisbenzamidine compounds of Formula (I) as antioxidant and as neuroprotective agents, wherein R1, R2, R3, R4 and L have the meaning defined in the claims.

  本发明涉及将式（I）的双苯基胍化合物用作抗氧化剂和神经保护剂，其中R1、R2、R3、R4和L的含义如权利要求所定义。
• BACTERIAL EFFLUX PUMP INHIBITORS FOR THE TREATMENT OF OPHTHALMIC AND OTIC INFECTIONS
  申请人：Bostian Keith

  公开号：US20080132457A1

  公开（公告）日：2008-06-05

  Efflux pump inhibitors are co-administered with antimicrobial agents for the treatment of ophthalmic or otic infections. The agents may be co-administered directly to the site of infection (e.g., the eye or ear).

  流出泵抑制剂与抗微生物药物一起联合使用，用于治疗眼科或耳科感染。这些药物可以直接共同应用于感染部位（例如眼睛或耳朵）。
• Trypanocidal Activity of Conformationally Restricted Pentamidine Congeners
  作者：Isaac O. Donkor、Tien L. Huang、Bin Tao、Donna Rattendi、Schennella Lane、Marc Vargas、Burt Goldberg、Cyrus Bacchi

  DOI：10.1021/jm020375q

  日期：2003.3.1

  A series of conformationally restricted congeners of pentamidine in which the flexible pentyl bridge of pentamidine was replaced by trans-1,2-bismethylenecyclopropyl, phenyl, pyridinyl, piperazinyl, homopiperazinyl, and piperidinyl groups were synthesized. The compounds were evaluated for trypanocidal activity in vitro and in vivo against one drug-sensitive and three drug-resistant trypanosome isolates. The DNA binding affinity of the compounds was also studied using calf thymus DNA and poly(dA-dT). The nature of the linker influenced the DNA binding affinity as well as the trypanocidal activity of the compounds. trans-1,2-Bis(4-amidinophenoxymethylene)cyclopropane (1) was over 25-fold more potent than pentamidine against the drug-resistant isolate KETRI 243As-10-3, albeit with comparable DNA binding affinity. NN'-Bis(4-amidinophenyl)homopiperazine (8) was the most potent trypanocide in vitro against all four trypanosome isolates studied, but N,N'-bis(4-amidinophenyl)piperazine (6) was the most effective agent in vivo against both drug-sensitive and drug-resistant trypanosomes.
• Bisbenzamidines for the Treatment of Pneumonia
  申请人：Walzer Peter D.

  公开号：US20080279917A1

  公开（公告）日：2008-11-13

  A method of combating infectious agents, such as Pneumocystis pneumonia, and a method of treating a subject in need of such treatment is disclosed. The method comprises administering to the subject a bis-benzamidoxime of formula (I) wherein the linker is a di-substituted cyclic moiety of any ring size and may contain at least one heteroatom; the aromatic group is 1,2-; 1,3-; or 1,4-disubstituted; R is selected from the group consisting of a hydrogen, a linear or branched alkyl group, containing from 1 to 20 carbon atoms; R′ is selected from the group consisting of a hydrogen, a linear or branched alkyl group containing from one to twenty carbon atoms, an aromatic ring, a cycloalkyl group containing three to eight carbon atoms, or a hydroxyl group; alternatively, R and R′ may form a cyclic structure that can be fused to another cyclic system; or a pharmaceutically acceptable salt thereof. Pharmaceutical formulations and active compounds useful in the practice of the present invention are also disclosed.