7-butyl-15-methyl-1,7,13-triazabicyclo[11.3.1]heptadec-15-ene-14,17-dione | 904316-14-9

• 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-butyl-15-methyl-1,7,13-triazabicyclo[11.3.1]heptadec-15-ene-14,17-dione
• 英文别名: 15-methyl-7-butyl-1,7,13-triazabicyclo[11.3.1]heptadeca-15-en-14,17-dione
• CAS: 904316-14-9
• 化学式: C₁₉H₃₃N₃O₂
• 分子量: 335.49
• InChiKey: AVPKSTUSGWBLKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-butyl-15-methyl-1,7,13-triazabicyclo[11.3.1]heptadec-15-ene-14,17-dione 、 癸基溴 以 乙腈 为溶剂， 反应 20.0h， 以33%的产率得到15-methyl-7-butyl-7-n-decyl-1,7,13-triazabicyclo[11.3.1]heptadeca-15-en-14,17-dione bromide
  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：

  1,5-二溴戊烷 在 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 7-butyl-15-methyl-1,7,13-triazabicyclo[11.3.1]heptadec-15-ene-14,17-dione
  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

文献信息

• Structure of pyrimidinocyclophanes in solution by NMR
  作者：Leisan Galiullina、Anton Nikolaev、Vyacheslav Semenov、Vladimir Reznik、Shamil Latypov

  DOI：10.1016/j.tet.2006.04.064

  日期：2006.7

  The conformations and self-associative properties of novel pyrimidinocyclophanes with a substituted nitrogen atom in a spacer have been studied using several independent NMR methods (NOE, aromatic shielding effect, 2D DOSY, GIAO DFT chemical shift calculations, DNMR) in a variety of solvents, in acidic and basic media. At room temperature the title compounds in neutral solution are in slow exchange on the NMR time-scale and exist in a folded conformation. In the acidic medium protonation occurs at the bridge nitrogen, and that leads to dramatic modifications of the structure and dynamics of the compound. The protonated form exists at the equilibrium of 'folded' and 'extended' conformers. Moreover, the protonated form is prone to association and can be effectively described as a dimer at room temperature. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.