2-Furan-2-yl-7-[2-(2,4,5-tribromo-phenyl)-ethyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine | 181622-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 2-Furan-2-yl-7-[2-(2,4,5-tribromo-phenyl)-ethyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine
• 英文别名: 4-(Furan-2-yl)-10-[2-(2,4,5-tribromophenyl)ethyl]-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(9),2,4,7,11-pentaene
• CAS: 181622-15-1
• 化学式: C₁₈H₁₁Br₃N₆O
• 分子量: 567.037
• InChiKey: VKIFWQIMFQETKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Furan-2-yl-7-[2-(2,4,5-tribromo-phenyl)-ethyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 在 盐酸 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 5-amino-7-[2-(2',4',5'-tribromo)phenylethyl]-2-(2-furyl)-pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  Synthesis of the tritium labeled SCH 58261, a new non-xanthine A2A adenosine receptor antagonist

  摘要：

  The tritium labeled form of 5-amino-7-(2-phenylethyl)-2-(2-furyl)-pyrazolo[4,3-e] 1,2,4-triazolo[1,5-c]pyrimidine (H-3-SCH 58261) was obtained by reduction of 5-amino-7-[2-(2',4',5'-tribromo)-phenylethyl]-2-(2-furyl)-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine with tritium gas in the presence of 10% Pd-C. Final product was purified by HPLC to give the title H-3-SCH 58261 with radiochemical purity of 99% and specific activity of 68.6 Ci/mmol. H-3-SCH 58261 bound A(2A) receptors in rat striatal membranes (specific binding > 90%) with K-d acid B-max value of 0.70 nM and 971 fmol/mg of protein, respectively. H-3-SCH 58261 represents a useful tool for a further characterization of A(2A) adenosine receptor subtype.

  DOI：

  10.1002/(sici)1099-1344(199608)38:8<725::aid-jlcr885>3.0.co;2-g
• 作为产物：
  描述：

  1-[2-(2',4',5'-tribromo)-phenylethyl]-4-cyano-3-aminopyrazole 反应 15.5h， 生成 2-Furan-2-yl-7-[2-(2,4,5-tribromo-phenyl)-ethyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  Synthesis of the tritium labeled SCH 58261, a new non-xanthine A2A adenosine receptor antagonist

  摘要：

  The tritium labeled form of 5-amino-7-(2-phenylethyl)-2-(2-furyl)-pyrazolo[4,3-e] 1,2,4-triazolo[1,5-c]pyrimidine (H-3-SCH 58261) was obtained by reduction of 5-amino-7-[2-(2',4',5'-tribromo)-phenylethyl]-2-(2-furyl)-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine with tritium gas in the presence of 10% Pd-C. Final product was purified by HPLC to give the title H-3-SCH 58261 with radiochemical purity of 99% and specific activity of 68.6 Ci/mmol. H-3-SCH 58261 bound A(2A) receptors in rat striatal membranes (specific binding > 90%) with K-d acid B-max value of 0.70 nM and 971 fmol/mg of protein, respectively. H-3-SCH 58261 represents a useful tool for a further characterization of A(2A) adenosine receptor subtype.

  DOI：

  10.1002/(sici)1099-1344(199608)38:8<725::aid-jlcr885>3.0.co;2-g

文献信息

• Pyrazolo[4,3-<i>e</i>]1,2,4-triazolo[1,5-<i>c</i>]pyrimidine Derivatives as Highly Potent and Selective Human A₃ Adenosine Receptor Antagonists:  Influence of the Chain at the N⁸ Pyrazole Nitrogen
  作者：Pier Giovanni Baraldi、Barbara Cacciari、Romeo Romagnoli、Giampiero Spalluto、Stefano Moro、Karl-Norbert Klotz、Edward Leung、Katia Varani、Stefania Gessi、Stefania Merighi、Pier Andrea Borea

  DOI：10.1021/jm001047y

  日期：2000.12.1

  IB-MECA was measured in membranes of CHO cells stably transfected with the human A(3) receptor. The new compounds are among the most potent and selective A(3) antagonists so far described. The derivatives with higher affinity at human A(3) adenosine receptors proved to be antagonists, in the cAMP assay, capable of inhibiting the effect of IB-MECA with IC(50) values in the nanomolar range, with a trend strictly

  先前已经报道了以初步形式（Baraldi等人，J.Med.Chem.1999，42，4473-4478）作为高效和选择性的人A（3）腺苷受体拮抗剂的一系列吡唑并三唑并嘧啶类化合物。合成的化合物显示在亚纳摩尔范围内的A（3）腺苷受体亲和力和在人类A（1），A（2A），A（2B）和A（3）腺苷的放射性配体结合测定中评估的高水平选择性受体。特别是，分析了该链在N（8）吡唑氮上的作用。这项研究使我们能够鉴定出在N（8）吡唑具有甲基的衍生物与在N（5）位置具有4-甲氧基苯基氨基甲酰基部分的衍生物是在亲和力和选择性（hA）方面均具有最佳结合特性的化合物（3）= 0.2 nM，hA（1）/ hA（3）= 5485，hA（2A）/ hA（3）= 6950，hA（2B）/ hA（3）= 1305）。在特定功能模型中，所有化合物均被证明是完全拮抗剂，其中在稳定转染了人A（3）受体的CHO细胞膜中测量了IB-M
• Synthesis of the tritium labeled SCH 58261, a new non-xanthine A2A adenosine receptor antagonist
  作者：Pier Giovanni Baraldi、Barbara Cacciari、Silvio Dionisotti、Judith Egan、Giampiero Spalluto、Cristina Zocchi

  DOI：10.1002/(sici)1099-1344(199608)38:8<725::aid-jlcr885>3.0.co;2-g

  日期：1996.8

  The tritium labeled form of 5-amino-7-(2-phenylethyl)-2-(2-furyl)-pyrazolo[4,3-e] 1,2,4-triazolo[1,5-c]pyrimidine (H-3-SCH 58261) was obtained by reduction of 5-amino-7-[2-(2',4',5'-tribromo)-phenylethyl]-2-(2-furyl)-pyrazolo[4,3-e]1,2,4-triazolo[1,5-c]pyrimidine with tritium gas in the presence of 10% Pd-C. Final product was purified by HPLC to give the title H-3-SCH 58261 with radiochemical purity of 99% and specific activity of 68.6 Ci/mmol. H-3-SCH 58261 bound A(2A) receptors in rat striatal membranes (specific binding > 90%) with K-d acid B-max value of 0.70 nM and 971 fmol/mg of protein, respectively. H-3-SCH 58261 represents a useful tool for a further characterization of A(2A) adenosine receptor subtype.