7,23-diethyl-16,32-dimethyl-1,7,13,17,23,29-hexaazatricyclo[23.3.1.1^13,17]tetratriaconta-15,31-diene-14,30,33,34-tetraone | 672906-64-8

• 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: 7,23-diethyl-16,32-dimethyl-1,7,13,17,23,29-hexaazatricyclo[23.3.1.1^13,17]tetratriaconta-15,31-diene-14,30,33,34-tetraone
• 英文别名: 7,23-Diethyl-16,30-dimethyl-1,7,13,17,23,29-hexazatricyclo[27.3.1.113,17]tetratriaconta-15,30-diene-14,32,33,34-tetrone；7,23-diethyl-16,30-dimethyl-1,7,13,17,23,29-hexazatricyclo[27.3.1.113,17]tetratriaconta-15,30-diene-14,32,33,34-tetrone
• CAS: 672906-64-8
• 化学式: C₃₄H₅₈N₆O₄
• 分子量: 614.872
• InChiKey: JSHSZFFINJVKJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  44
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  癸基溴 、 7,23-diethyl-16,32-dimethyl-1,7,13,17,23,29-hexaazatricyclo[23.3.1.1^13,17]tetratriaconta-15,31-diene-14,30,33,34-tetraone 以 乙腈 为溶剂， 反应 20.0h， 以90%的产率得到16,30-dimethyl-7,23-diethyl-7,23-di-n-decyl-1,7,13,17,23,29-hexaazatricyclo[27,3,1,1^11,15]-tetratriaconta-15,30-diene-14,32,33,34-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(5-bromopentyl)-6-methyluracil 在 potassium carbonate 作用下， 以 异丙醇 、 乙腈 为溶剂， 反应 127.0h， 生成 7,23-diethyl-16,32-dimethyl-1,7,13,17,23,29-hexaazatricyclo[23.3.1.1^13,17]tetratriaconta-15,31-diene-14,30,33,34-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

• Macrocyclic derivatives of 6-methyluracil as ligands of the peripheral anionic site of acetylcholinesterase
  作者：Vyacheslav E. Semenov、Rashit Kh. Giniyatullin、Sofya V. Lushchekina、Ekaterina D. Kots、Konstantin A. Petrov、Alexandra D. Nikitashina、Oksana A. Minnekhanova、Vladimir V. Zobov、Evgeny E. Nikolsky、Patrick Masson、Vladimir S. Reznik

  DOI：10.1039/c4md00225c

  日期：——

  selectivity for human acetylcholinesterase (AChE), with an inhibitory power 100–200 times higher than for human butyrylcholinesterase (BChE). Docking simulations indicate specific binding of pyrimidinophanes 2a and 4 onto the peripheral anionic site of AChE. Other compounds bind to the active center of AChE as well as to the peripheral anionic site. These compounds are dual binding site inhibitors. Pyrimidinophane

  制备了具有两个邻-硝基苄基乙基二烷基铵头与不同间隔基桥接的新型嘧啶并烷。嘧啶二烯醚2a，2b和3是胆碱酯酶的可逆抑制剂。它们显示出对人乙酰胆碱酯酶（AChE）的很好的选择性，其抑制力比对人丁酰胆碱酯酶（BChE）高100-200倍。对接模拟表明嘧啶二烷2a和4与AChE的外围阴离子位点有特异性结合。其他化合物与AChE的活性中心以及周围的阴离子位点结合。这些化合物是双重结合位点抑制剂。嘧啶二烷2b及其无环对应物1在重症肌无力的动物模型中进行了测试，可以被认为是治疗病理性肌无力综合征的有价值的候选药物。
• 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.