8-bromo-1,3-dimethyl-7-propargyl-3,7-dihydro-1H-purine-2,6-dione | 115919-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 8-bromo-1,3-dimethyl-7-propargyl-3,7-dihydro-1H-purine-2,6-dione
• 英文别名: 7-(prop-2-yn-1-yl)-8-bromo-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione；8-bromo-1,3-dimethyl-7-(prop-2-yn-1-yl)-3,7-dihydro-1H-purine-2,6-dione；8-bromo-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione；7-propargyl-8-bromo-1,3-dimethyl-3,7-dihydropurine-2,6-dione；Qxhdcpfrmxskgn-uhfffaoysa-；8-bromo-1,3-dimethyl-7-prop-2-ynylpurine-2,6-dione
• CAS: 115919-19-2
• 化学式: C₁₀H₉BrN₄O₂
• 分子量: 297.111
• InChiKey: QXHDCPFRMXSKGN-UHFFFAOYSA-N

物化性质

• 熔点：
  189-191 °C
• 沸点：
  461.6±55.0 °C(predicted)
• 密度：
  1.66±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 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：

  8-bromo-1,3-dimethyl-7-propargyl-3,7-dihydro-1H-purine-2,6-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以82%的产率得到8-Hydrazinyl-1,3-dimethyl-7-prop-2-ynylpurine-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：

  茶碱 在 溴 、 sodium acetate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 8-bromo-1,3-dimethyl-7-propargyl-3,7-dihydro-1H-purine-2,6-dione
  参考文献：
  名称：

  作为新型 DPP-4 抑制剂的利格列汀的 1,2,3-三唑类似物的合成：DFT，分子对接方法

  摘要：

  摘要 如本文所述，从 CuI 催化的N-炔丙基嘌呤和几种芳基叠氮化物之间的 1,3-偶极环加成反应合成一些新型 1,2,3-三唑基利格列汀衍生物。进一步评估了所有这些新化合物的体外二肽基肽酶 4 (DPP-4) 活性和化合物 8-bromo-1,3-dimethyl-7-((1-(3-(trifluoromethyl)phenyl)-1 H -1,2,3-triazol-4-yl)methyl)-1 H -purine-2,6(3 H ,7 H )-dione, 7-(but-2-yn-1-yl)-1 ,3-二甲基-8-(4-((1-(3-(三氟甲基)苯基)-1H-1,2,3-三唑-4-基)甲基)哌嗪-1-基) -1H-嘌呤-2,6(3 H ,7 H )-二酮和 7-(but-2-yn-1-yl)-8-(4-((1-(3,5-二氯苯基)-1H -1,2,3-triazol-4-yl)met

  DOI：

  10.1134/s1068162023030214

文献信息

• Synthesis and Biological Evaluation of Novel Fused [1,2,3]Triazolo[4',5':3,4] pyrrolo[2,1-f]purines as Potent Anti-Proliferative Agents
  作者：E. Ramya Sucharitha、N. Satheesh Kumar、M. Ravinder、N. Vasudeva Reddy、Sirassu Narsimha

  DOI：10.1134/s1068162021040208

  日期：2021.7

  Abstract In search of the best anticancer agents, a series of novel fused [1,2,3]triazolo[4',5':3,4] pyrrolo[2,1-f]purine derivatives in one vessel was synthesized using 8-bromo-1,3-dimethyl-7-(prop-2-yn-1-yl)-1H-purine-2,6(3H,7H)-dione and various arylazides. The newly synthesized derivatives were evaluated for their in vitro anti-proliferative activity against four human cancer cell lines (MCF-7

  摘要 在寻找最佳抗癌剂，一系列新的稠合的[1,2,3]三唑并[4' ，5' ：3,4]吡咯并[2,1- ˚F使用8-]在一个容器中的嘌呤衍生物的合成溴-1,3-二甲基-7-(prop-2-yn-1-yl)-1H-purine-2,6(3 H ,7 H )-dione 和各种芳基叠氮化物。评估了新合成的衍生物对四种人类癌细胞系（MCF-7、HeLa、A-549 和 U-87MG）的体外抗增殖活性。3-(3,5-二氯苯基)-5,7-二甲基-7,10-二氢-[1,2,3]三唑并[4',5':3,4]吡咯并[2,1- f ]嘌呤-6,8(3 H ,5 H )-二酮和 5,7-二甲基-3-(4-硝基苯基)-3,10-二氢-[1,2,3]三唑并[4',5':3.4 ]pyrrolo[2,1 - f ]purine-6,8 (5 H ,7H )-二酮对 MCF-7 和 A-549 显示出更强的活性，IC
• 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.
• 7,8-Disubstituted [1,3]-thiazino-[2,3-f]-purine derivatives
  作者：Dušan Hesek、Alfonz Rybár

  DOI：10.1007/bf00810022

  日期：1993.11

  7-Cyanomethyl-8-ethoxycarbonylmethylthio- (3a), 7-cyanomethyl-8-cyanomethylthio- (3b), and 7-ethoxycarbonylmethyl-8-ethoxycarbonylmethylthio-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione (3c) afforded 7-amino-8-ethoxycarbonyl-(5), 7-amino-8-cyano- (6), and 8-ethoxycarbonyl-7-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-6H-[1,3]-thiazino-[2,3-f]-purine (7), respectively, on intramolecular Claisen-type condensation.
• 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：——