N-{3-[(3-aminopropyl)(methyl)amino]propyl}-9-methyl-1-phenazinecarboxamide | 206531-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-{3-[(3-aminopropyl)(methyl)amino]propyl}-9-methyl-1-phenazinecarboxamide
• 英文别名: N-[3-[3-aminopropyl(methyl)amino]propyl]-9-methylphenazine-1-carboxamide
• CAS: 206531-16-0
• 化学式: C₂₁H₂₇N₅O
• 分子量: 365.478
• InChiKey: PZVUHQOXCDUMNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  84.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methylacridine-4-carboxylic acid imidazolide 、 N-{3-[(3-aminopropyl)(methyl)amino]propyl}-9-methyl-1-phenazinecarboxamide 以 四氢呋喃 为溶剂， 生成 9-methyl-N-{3-[{3-[(5-methyl-4-acridinylcarbonyl)amino]propyl}(methyl)amino]propyl}-1-phenazinecarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of unsymmetrical bis(arylcarboxamides) designed as topoisomerase-Targeted anticancer drugs

  摘要：

  Symmetrical dimers of lipophilic intercalating chromophores linked by cation-containing chains have recently been shown to have broad-spectrum in vivo anticancer activity. We report the preparation and evaluation of a series of both symmetric and unsymmetric dimers of a variety of intercalating chromophores of varied DNA binding strength, including naphthalimides, acridines, phenazines, oxanthrenes and 2-phenylquinolines. The unsymmetrical dimers were prepared by sequential coupling of the chromophores to linkers with selectively protected primary terminal amines to ensure high yields and unequivocal product. Protection of the internal (secondary) amines as BOC derivatives was used to ensure complete structural specificity, and was also an aid to the purification of these very polar compounds. The growth inhibitory abilities (as IC50 values) of the compounds in a range of cell lines showed that the nature of the linker chain was important, and independent of the nature of the chromophore, with compounds containing the dicationic linker [-(CH2)(2)NH(CH2)(2)NH(CH2)(2)-] being on average 30-fold more potent than the corresponding compounds containing the monocationic linker [-(CH2)(3)NMe(CH2)(3)-]. However, the chromophores also play a role in determining biological activity, with the cytotoxicities of symmetric and unsymmetric dicationic dimers correlating with the overall DNA binding abilities of the chromophores. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00249-8
• 作为产物：
  描述：

  tert-butyl 3-(methyl{3-[(9-methyl-1-phenazinylcarbonyl)amino]propyl}amino)propyl carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到N-{3-[(3-aminopropyl)(methyl)amino]propyl}-9-methyl-1-phenazinecarboxamide
  参考文献：
  名称：

  Synthesis and evaluation of unsymmetrical bis(arylcarboxamides) designed as topoisomerase-Targeted anticancer drugs

  摘要：

  Symmetrical dimers of lipophilic intercalating chromophores linked by cation-containing chains have recently been shown to have broad-spectrum in vivo anticancer activity. We report the preparation and evaluation of a series of both symmetric and unsymmetric dimers of a variety of intercalating chromophores of varied DNA binding strength, including naphthalimides, acridines, phenazines, oxanthrenes and 2-phenylquinolines. The unsymmetrical dimers were prepared by sequential coupling of the chromophores to linkers with selectively protected primary terminal amines to ensure high yields and unequivocal product. Protection of the internal (secondary) amines as BOC derivatives was used to ensure complete structural specificity, and was also an aid to the purification of these very polar compounds. The growth inhibitory abilities (as IC50 values) of the compounds in a range of cell lines showed that the nature of the linker chain was important, and independent of the nature of the chromophore, with compounds containing the dicationic linker [-(CH2)(2)NH(CH2)(2)NH(CH2)(2)-] being on average 30-fold more potent than the corresponding compounds containing the monocationic linker [-(CH2)(3)NMe(CH2)(3)-]. However, the chromophores also play a role in determining biological activity, with the cytotoxicities of symmetric and unsymmetric dicationic dimers correlating with the overall DNA binding abilities of the chromophores. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00249-8

文献信息

• Dna-targeted benzotriazine 1,4-dioxides and their use in cancer therapy
  申请人：Brown Martin J.

  公开号：US20070191372A1

  公开（公告）日：2007-08-16

  The present invention relates to DNA-targeted 1,2,4-benzotriazine-1,4-dioxides and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及以DNA为靶点的1,2,4-苯并三氮唑-1,4-二氧化物及其相关类似物，其制备方法以及它们作为低氧选择性药物和放射增敏剂在癌症治疗中的使用，可以单独使用或与放射线和/或其他抗癌药物结合使用。
• US6114332A
  申请人：——

  公开号：US6114332A

  公开（公告）日：2000-09-05