6,20-diethyl-14,28-dimethyl-1,6,11,15,20,25-hexaazatricyclo[23.3.1.1^11,15]triaconta-13,27-diene-12,26,29,30-tetraone | 672906-62-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6,20-diethyl-14,28-dimethyl-1,6,11,15,20,25-hexaazatricyclo[23.3.1.1^11,15]triaconta-13,27-diene-12,26,29,30-tetraone
• 英文别名: 6,20-Diethyl-14,26-dimethyl-1,6,11,15,20,25-hexazatricyclo[23.3.1.111,15]triaconta-13,26-diene-12,28,29,30-tetrone；6,20-diethyl-14,26-dimethyl-1,6,11,15,20,25-hexazatricyclo[23.3.1.111,15]triaconta-13,26-diene-12,28,29,30-tetrone
• CAS: 672906-62-6
• 化学式: C₃₀H₅₀N₆O₄
• 分子量: 558.765
• InChiKey: NERAWTLCZWAEOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  40
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 6,20-diethyl-14,28-dimethyl-1,6,11,15,20,25-hexaazatricyclo[23.3.1.1^11,15]triaconta-13,27-diene-12,26,29,30-tetraone 以 乙腈 为溶剂， 反应 20.0h， 以75%的产率得到14,26-dimethyl-6,20-diethyl-6,20-dibenzyl-1,6,11,15,20,25-hexaazatricyclo[23,3,1,1^11,15]-triaconta-13,26-diene-12,28,29,30-tetraone dibromide
  参考文献：
  名称：

  Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers

  摘要：

  The reactions of 1,3-bis(alpha,omega-bromoalkyl)-6-methyluracils with 1,3-bis(alpha,omega-ethylaminoalkyl)-6-methyluracils or 1,3-bis(bromopentyl)thymine with butylamine afforded pyrimidinophanes containing one or two uracil units and nitrogen atoms in bridging polymethylene chains. In some cases individual geometric isomers of pyrimidinophanes differing in the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings were isolated. Quaternization of the bridging nitrogen atom with o-nitrobenzyl bromide, benzyl bromide, n-decyl bromide gave rise to water-soluble pyrimidinophanes which were evaluated for their antibacterial and antifungal activity. The arrangement of the carbonyl groups in macrocycles doesn't affect the activity. Antibacterial and antifungal activity of pyrimidinophanes increases with the increase of polymethylene N-(pyr)-N-chain length and dramatically increases upon the introduction of n-decyl substituent at nitrogen atoms in spacers. Pyrimidi-nophanes with 5 and 6 methylene groups in N(pyr)-N-chain and n-decyl substituent showed significant bacteriostatic, fungistatic, bactericidal, fungicidal activity which comparable with standard antibacterial and antifungal drugs. Acyclic counterpart demonstrated the highest activity against fungi. Toxicity of more effective pyrimidinophanes was determined for mice and Daphnia magna Straus. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.03.030
• 作为产物：
  描述：

  1,3-bis(ω-bromobutyl)-6-methyluracil 在 potassium carbonate 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 127.0h， 生成 6,20-diethyl-14,28-dimethyl-1,6,11,15,20,25-hexaazatricyclo[23.3.1.1^11,15]triaconta-13,27-diene-12,26,29,30-tetraone
  参考文献：
  名称：

  摘要：

  The reactions of 1,3-bis(omega-bromobutyl- or -pentyl)-6-methyluracil with 1,3-bis(omega-ethyl-aminobutyl- or -pentyl)-6-methyluracil afforded pyrimidinophanes containing N atoms in bridging polymethylene chains. Individual geometric isomers of pyrimidinophanes were isolated. The structure of one of these isomers was established by X-ray diffraction analysis. Quaternization of the bridging N atoms with o-nitrobenzyl bromide gave rise to water-soluble pyrimidinophanes.

  DOI：

  10.1023/a:1025653328231

文献信息

• Copper(II) bromide complexes with acyclic and cyclic pyrimidine-containing phane ligands
  作者：V. E. Semenov、V. I. Morozov、A. V. Chernova、R. R. Shagidullin、A. S. Mikhailov、R. Kh. Giniyatullin、V. D. Akamsin、V. S. Reznik

  DOI：10.1134/s1070328407090114

  日期：2007.9

  Complexes of copper(II) bromide with cyclic and isostructural acyclic phane ligands containing derivatives of pyrimidine nucleobases (cytosine and uracil) were synthesized and characterized. In two cyclic pyrimidinophanes used, the macrocycles included two 6-methylthiocytosine and one 6-methyluracil units linked by polymethylene chains (L-3) and two 6-methyluracil units linked by N-containing bridges (L-5). Ligand L-3 and its isostructural acyclic analogs are coordinated by the Cu2+ ion through the same donor sites (the ring N atoms of the thiocytosine units). The coordination polyhedra of the Cu atom in complexes with cyclic and acyclic ligands are different. Ligand L-5 and its isostructural acyclic analog also form copper(II) complexes with different coordination polyhedra involving different donor sites. The acyclic ligand is coordinated by the Cu2+ ion via the bridging N atom, while cyclic ligand L-5, via the uracil CO groups (the bridging N atoms become protonated). The resulting complexes are dielectrics.
• Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers
  作者：V.E. Semenov、A.D. Voloshina、E.M. Toroptzova、N.V. Kulik、V.V. Zobov、R.K. Giniyatullin、A.S. Mikhailov、A.E. Nikolaev、V.D. Akamsin、V.S. Reznik

  DOI：10.1016/j.ejmech.2006.03.030

  日期：2006.9

  The reactions of 1,3-bis(alpha,omega-bromoalkyl)-6-methyluracils with 1,3-bis(alpha,omega-ethylaminoalkyl)-6-methyluracils or 1,3-bis(bromopentyl)thymine with butylamine afforded pyrimidinophanes containing one or two uracil units and nitrogen atoms in bridging polymethylene chains. In some cases individual geometric isomers of pyrimidinophanes differing in the mutual arrangement of the carbonyl and methyl groups at different pyrimidine rings were isolated. Quaternization of the bridging nitrogen atom with o-nitrobenzyl bromide, benzyl bromide, n-decyl bromide gave rise to water-soluble pyrimidinophanes which were evaluated for their antibacterial and antifungal activity. The arrangement of the carbonyl groups in macrocycles doesn't affect the activity. Antibacterial and antifungal activity of pyrimidinophanes increases with the increase of polymethylene N-(pyr)-N-chain length and dramatically increases upon the introduction of n-decyl substituent at nitrogen atoms in spacers. Pyrimidi-nophanes with 5 and 6 methylene groups in N(pyr)-N-chain and n-decyl substituent showed significant bacteriostatic, fungistatic, bactericidal, fungicidal activity which comparable with standard antibacterial and antifungal drugs. Acyclic counterpart demonstrated the highest activity against fungi. Toxicity of more effective pyrimidinophanes was determined for mice and Daphnia magna Straus. (c) 2006 Elsevier SAS. All rights reserved.
• ——
  作者：R. Kh. Giniyatullin、A. S. Mikhailov、V. E. Semenov、V. D. Akamsin、V. S. Reznik、A. V. Chernova、G. M. Doroshkina、A. A. Nafikova、Sh. K. Latypov、Yu. Ya. Efremov、D. R. Sharafutdinova、A. T. Gubaidullin、I. A. Litvinov

  DOI：10.1023/a:1025653328231

  日期：——

  The reactions of 1,3-bis(omega-bromobutyl- or -pentyl)-6-methyluracil with 1,3-bis(omega-ethyl-aminobutyl- or -pentyl)-6-methyluracil afforded pyrimidinophanes containing N atoms in bridging polymethylene chains. Individual geometric isomers of pyrimidinophanes were isolated. The structure of one of these isomers was established by X-ray diffraction analysis. Quaternization of the bridging N atoms with o-nitrobenzyl bromide gave rise to water-soluble pyrimidinophanes.