N,N'-bis(4-amidinophenyl)-1,3-benzodicarboxamide dihydrochloride | 5300-74-3

• 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: N,N'-bis(4-amidinophenyl)-1,3-benzodicarboxamide dihydrochloride
• 英文别名: 1-N,3-N-bis(4-carbamimidoylphenyl)benzene-1,3-dicarboxamide;hydrochloride
• CAS: 5300-74-3
• 化学式: C₂₂H₂₀N₆O₂*2ClH
• 分子量: 473.362
• InChiKey: MONMXLOTBLFXJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  7
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N¹,N³-bis(4-cyanophenyl)isophthalamide 在 盐酸 、 氨 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 77.0h， 生成 N,N'-bis(4-amidinophenyl)-1,3-benzodicarboxamide dihydrochloride
  参考文献：
  名称：

  Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine

  摘要：

  A series of conformationally restricted analogues of pentamidine in which the flexible central bridge has been replaced by trans-cyclopropyl, phenyl, pyridinyl, piperazinyl or homopiperazinyl groups as conformationally restricted linkers have been synthesized. The anti-Pneumocystis carinii activity of these compounds was evaluated in a cell culture model and the DNA binding affinity was determined by thermal denaturation measurements. At 1 mu M, compounds 2, 3, 5, 7, 9 and pentamidine were highly effective and caused total inhibition of P. carinii growth in culture. At 0.1 mu M, compounds 2, 5, 7 and 10 were more active than pentamidine with N, N'-bis(4-amidinophenyl)piperazine 7 being approximately 15-fold more effective than pentamidine. The most active compounds, 7 and 10, showed strong binding affinities for calf thymus DNA and poly(dA-dT); however, a clear correlation between DNA binding affinity and the in vitro anti-P. carinii activity of these compounds was not observed. The results suggest that the nature of the central Linker influences the biological actions of these compounds. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80102-0

文献信息

• Novel bisbenzamidines as potential drug candidates for the treatment of Pneumocystis carinii pneumonia
  作者：Jean Jacques Vanden Eynde、Annie Mayence、Tien L Huang、Margaret S Collins、Sandra Rebholz、Peter D Walzer、Melanie T Cushion

  DOI：10.1016/j.bmcl.2004.06.034

  日期：2004.9

  A series of pentamidine congeners has been synthesized and screened for their in vitro activity against Pneumocystis carinii. Among the tested compounds, bisbenzamidines linked by a flexible pentanediamide or hexanediamide chain (7 and 9) emerged as exceptionally potent agents that were more effective and less toxic than pentamidine in the assays described in this study. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and anti-Pneumocystis carinii activity of conformationally restricted analogues of pentamidine
  作者：Bin Tao、Tien L Huang、Qian Zhang、Latasha Jackson、Sherry F Queener、Isaac O Donkor

  DOI：10.1016/s0223-5234(99)80102-0

  日期：1999.6

  A series of conformationally restricted analogues of pentamidine in which the flexible central bridge has been replaced by trans-cyclopropyl, phenyl, pyridinyl, piperazinyl or homopiperazinyl groups as conformationally restricted linkers have been synthesized. The anti-Pneumocystis carinii activity of these compounds was evaluated in a cell culture model and the DNA binding affinity was determined by thermal denaturation measurements. At 1 mu M, compounds 2, 3, 5, 7, 9 and pentamidine were highly effective and caused total inhibition of P. carinii growth in culture. At 0.1 mu M, compounds 2, 5, 7 and 10 were more active than pentamidine with N, N'-bis(4-amidinophenyl)piperazine 7 being approximately 15-fold more effective than pentamidine. The most active compounds, 7 and 10, showed strong binding affinities for calf thymus DNA and poly(dA-dT); however, a clear correlation between DNA binding affinity and the in vitro anti-P. carinii activity of these compounds was not observed. The results suggest that the nature of the central Linker influences the biological actions of these compounds. (C) Elsevier, Paris.