7-烯丙基-8-溴-1,3-二甲基-1H-嘌呤-2,6-(3H,7H)-二酮 | 82463-67-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 7-烯丙基-8-溴-1,3-二甲基-1H-嘌呤-2,6-(3H,7H)-二酮
• 英文名称: 7-allyl-8-bromotheophylline
• 英文别名: 7-allyl-8-bromo-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione；N7-allyl-8-bromotheophylline；7-Allyl-8-brom-theophyllin；7-allyl-8-bromo-1,3-dimethyl-3,7-dihydro-purine-2,6-dione；8-bromo-1,3-dimethyl-7-prop-2-enylpurine-2,6-dione
• CAS: 82463-67-0
• 化学式: C₁₀H₁₁BrN₄O₂
• 分子量: 299.127
• InChiKey: GNCMXCGTXLKHJF-UHFFFAOYSA-N

物化性质

• 熔点：
  144-145 °C(Solv: ethanol (64-17-5))
• 沸点：
  450.9±55.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-烯丙基-8-溴-1,3-二甲基-1H-嘌呤-2,6-(3H,7H)-二酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以88%的产率得到7-allyl-8-hydrazino-1,3-dimethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  New [f]-Fused Theophyllines: A Simple One-Step Synthesis of the Pyrimido[2,1-f]purine System via 8-Azidopurines

  摘要：

  描述了一种从7-(2-烯基)-或7-(2-炔基)-8-叠氮茶碱出发制备新型四氢和六氢嘧啶并[2,1-f]嘌呤的方法。

  DOI：

  10.1055/s-1989-27355
• 作为产物：
  描述：

  8-溴茶碱 、 3-溴丙烯 在 氢氧化钾 作用下， 生成 7-烯丙基-8-溴-1,3-二甲基-1H-嘌呤-2,6-(3H,7H)-二酮
  参考文献：
  名称：

  New [f]-Fused Theophyllines: A Simple One-Step Synthesis of the Pyrimido[2,1-f]purine System via 8-Azidopurines

  摘要：

  描述了一种从7-(2-烯基)-或7-(2-炔基)-8-叠氮茶碱出发制备新型四氢和六氢嘧啶并[2,1-f]嘌呤的方法。

  DOI：

  10.1055/s-1989-27355

文献信息

• Synthesis of palladium complexes with anionic N,NR- or neutral NH,NR-theophylline-derived NHC ligands
  作者：Mareike C. Jahnke、Alexandre Hervé、Florian Kampert、F. Ekkehardt Hahn

  DOI：10.1016/j.ica.2020.120055

  日期：2021.1

  oxidative addition to give complexes of type trans-[Pd(theophyllinato)X(PPh3)2] (trans-[5]−trans-[8]). The protonation of the unsubstituted theophyllinato ring-nitrogen atom to give the pNHC complexes was achieved either by performing the oxidative addition of 1 in the presence of NH4BF4 to give complex trans-[9]BF4 or by N-protonation of the coordinated theophyllinato ligand in trans-[6]−trans-[8] with

  摘要制备了四个具有N7-甲基或N7-烯丙基和C8-氯或C8-溴取代基的C8卤代茶碱（1-4）。卤代茶碱与[Pd（PPh3）4]发生氧化加成反应，生成反式-[Pd（theophyllinato）X（PPh3）2]（反式-[5]-反式-[8]）型配合物。通过在NH4BF4存在下进行氧化加成1生成复合物反式[9] BF4或通过对配位的茶碱素配体进行N质子化，可实现未取代的茶碱素环氮原子的质子化以生成pNHC配合物。反式[6]-反式-[8]与HBF4·Et2O生成复合物反式[10] BF4--反式[12] BF4。反式[5]，反式[7]，反式[9] BF4，通过X射线衍射测定反式-[11] BF4和反式-[12] BF4，结果表明茶碱衍生的五元二氨基杂环化合物中可比较的度量参数存在显着差异。没有观察到N-烯丙基取代基与金属中心的相互作用。
• New 8-aminoalkyl derivatives of purine-2,6-dione with arylalkyl, allyl or propynyl substituents in position 7, their 5-HT1A, 5-HT2A, and 5-HT7 receptor affinity and pharmacological evaluation
  作者：Grażyna Chłoń-Rzepa、Paweł Żmudzki、Grzegorz Satała、Beata Duszyńska、Anna Partyka、Dagmara Wróbel、Magdalena Jastrzębska-Więsek、Anna Wesołowska、Andrzej J. Bojarski、Maciej Pawłowski、Paweł Zajdel

  DOI：10.1016/s1734-1140(13)70960-5

  日期：2013.1

  Background: Our previous studies in a group of arylpiperazine derivatives of 1,3-dimethyl-3,7-dihydro-purine-2,6-diones, aimed at chemical diversification of the purine-2,6-dione by introduction of hydrophobic substituent in a 7- or 8- position or elongation of the linker length between arylpiperazine and purine core, allowed a selection of potent 5-HT1A, 5-HT2A and 5-HT7 receptor ligands displaying anxiolytic and antidepressant properties. Continuing our research in this field, in the present studies we designed a new series of 8-aminoalkylamino (15-35) and 8-arylpiperazinylpropoxy (36-42) derivatives of 7-substituted 1,3-dimethyl-3,7-dihydropurine-2,6-dione as potential 5-HT1A, 5-HT2A and 5-HT7 receptor ligands with potential psychotropic activity. Methods: Radioligand binding assays were employed for determining the affinity and the selectivity profile of the synthesized compounds for native 5-HT1A, 5-HT2A, and cloned 5-HT6 and 5-HT7 receptors. The functional activity of the selected compounds at 5-HT1A and 5-HT2A receptors was tested in the commonly used in vivo models. Antidepressant and anxiolytic properties were evaluated in the forced swim (FST) and the four-plate test (FPT) in mice, respectively. Results: Among the evaluated series, selected 7-benzyl-8-((4-(4-(3-chlorophenyl)piperazin-1-yl)butyl)amino)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (21), a mixed 5-HT1A/5-HT2A/5-HT7 receptor ligand, produced an antidepressant-like effect in FST, and exerted anxiolytic-like activity in FPT. Another pharmacologically evaluated compound 42 (a mixed 5-HT1A/5-HT7 ligand) slightly, but non-significantly attenuated the immobility time of mice in FST and was devoid of activity in FPT. Conclusions: Study revealed advantage of mixed 5-HT1A/5-HT2A/5-HT7 receptor ligands over 5-HT1A/5-HT7 agents to display antidepressant- and anxiolytic-like activity. Modification of arylalkyl/allyl substituent in position 7 of purine-2,6-dione opens possibility for designing new 5-HT ligands with preserved p electron system and lower molecular weight.
• Pawlowski, Maciej; Gorczyca, Maria, Polish Journal of Chemistry, 1981, vol. 55, # 4, p. 837 - 841
  作者：Pawlowski, Maciej、Gorczyca, Maria

  DOI：——

  日期：——
• HESEK, DUSAN;, TEGZA MARIAN;RYBAR, ALFONZ;POVAZANEC, FRANTISEK, SYNTHESIS,(1989) N, C. 681-683
  作者：HESEK, DUSAN、, TEGZA MARIAN、RYBAR, ALFONZ、POVAZANEC, FRANTISEK

  DOI：——

  日期：——
• New [<i>f</i>]-Fused Theophyllines: A Simple One-Step Synthesis of the Pyrimido[2,1-<i>f</i>]purine System via 8-Azidopurines
  作者：Dušan Hesek、Marian Tegza、Alfonz Rybár、František Považanec

  DOI：10.1055/s-1989-27355

  日期：——

  An approach to novel tetrahydro- and hexahydropyrimido[2,1-f] purines starting from 7-(2-alkenyl)- or 7-(2-alkynyl)-8-azidotheophyllines is described.

  描述了一种从7-(2-烯基)-或7-(2-炔基)-8-叠氮茶碱出发制备新型四氢和六氢嘧啶并[2,1-f]嘌呤的方法。