2-[5-Amino-8-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate | 515160-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[5-Amino-8-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate
• CAS: 515160-67-5
• 化学式: C₂₂H₁₈F₃N₇O₃S
• 分子量: 517.491
• InChiKey: CLKNAICAXRZRBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-[5-Amino-8-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate 、 1-[4-(2-甲氧基乙氧基)苯基]哌嗪 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-[4-[4-(2-Methoxyethoxy)phenyl]piperazin-1-yl]ethyl]-8-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[5,1-f]purin-5-amine
  参考文献：
  名称：

  3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A2A antagonists

  摘要：

  A novel series of 3-substituted-8-aryl-[1,2,4]-triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A(2A) receptor antagonists with improved selectivity over the A(1) receptor, physiochemical properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound 27 displayed both superior in vitro and highly promising in vivo profiles. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.104
• 作为产物：
  描述：

  2-(三氟甲基)苯甲酸酰肼 在 N,O-双三甲硅基乙酰胺 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 生成 2-[5-Amino-8-[2-(trifluoromethyl)phenyl]-[1,2,4]triazolo[5,1-f]purin-3-yl]ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A2A antagonists

  摘要：

  A novel series of 3-substituted-8-aryl-[1,2,4]-triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A(2A) receptor antagonists with improved selectivity over the A(1) receptor, physiochemical properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound 27 displayed both superior in vitro and highly promising in vivo profiles. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.104

文献信息

• [EN] IMIDAZO (4,3-E)-1,2,4-TRIAZOLO(1,5-C) PYRIMIDINES AS ADENOSINE A2A RECEPTOR ANTAGONISTS<br/>[FR] IMIDAZO (4,3-E)-1,2,4-TRIAZOLO(1,5-C) PYRIMIDINES, EN TANT QU'ANTAGONISTES DES RECEPTEURS D'ADENOSINE A2A
  申请人：SCHERING CORP

  公开号：WO2003032996A1

  公开（公告）日：2003-04-24

  Compounds having the structural formula (I) or a pharmaceutically acceptable salt thereof, wherein R is optionally substituted phenyl or heteroaryl, cycloalkenyl, -C(=CH2)CH3, -C°C-CH3, -CH=C(CH3)2, X is alkylene, -C(O)CH2- or -C(O)N(R2)CH2-;Y is -N(R2)CH2CH2N(R3)-, -OCH2CH2N(R2)-, -O-, -S-, -CH2S-, -(CH2)2-N(R2)-, or optionally substituted divalent heteroaryl, piperidinyl or piperazinyl; and Z is optionally substituted phenyl, phenylalkyl or heteroaryl, diphenylmethyl or R6-C(O)-; or when Y is formula (II) Z is also R6-SO2-, R7-N(R8)-C(O)-, R7-N(R8)-C(S)- or R6OC(O)-;or when Y is 4-piperidinyl, Z can be phenylamino or pyridylamino; or Z and Y together are substituted piperidinyl, substituted pyrrolidinyl or substituted phenyl; R14 is H, halogen or optionally substituted alkyl; and Q, Q1, m, n, R2, R3, R4, R6, R7 and R8 are as defined in the specification are disclosed, their use in the treatment of Parkinson's disease, alone or in combination with other agents for treating Parkinson's disease, and pharmaceutical compositions comprising them.

  具有结构式(I)或其药学上可接受的盐的化合物，其中R是可选取代的苯基或杂环基，环烷基，-C（= CH2）CH3，-C°C-CH3，-CH = C（CH3）2，X是烷基，-C（O）CH2-或-C（O）N（R2）CH2-;Y是-N（R2）CH2CH2N（R3）-，-OCH2CH2N（R2）-，-O-，-S-，-CH2S-，-（CH2）2-N（R2）-，或可选取代的二价杂环基，哌啶基或哌嗪基;Z是可选取代的苯基，苯基烷基或杂环基，二苯甲基或R6-C（O）-;或当Y为公式（II）时，Z也是R6-SO2-，R7-N（R8）-C（O）-，R7-N（R8）-C（S）-或R6OC（O）-;或当Y为4-哌啶基时，Z可以是苯基氨基或吡啶基氨基;或Z和Y在一起是取代哌啶基，取代吡咯烷基或取代苯基;R14是H，卤素或可选取代的烷基;以及Q，Q1，m，n，R2，R3，R4，R6，R7和R8如规范所定义的，其在单独或与其他治疗帕金森病的药物一起使用时，以及包含它们的制药组合物中的用途。
• IMIDAZO[4,3-E]-1,2,4-TRIAZOLO[1,5-C]PYRIMIDINES AS ADENOSINE A2A RECEPTOR ANTAGONISTS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1435960B1

  公开（公告）日：2014-07-30
• 3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A2A antagonists
  作者：Lisa S. Silverman、John P. Caldwell、William J. Greenlee、Eugenia Kiselgof、Julius J. Matasi、Deen B. Tulshian、Leyla Arik、Carolyn Foster、Rosalia Bertorelli、Angela Monopoli、Ennio Ongini

  DOI：10.1016/j.bmcl.2006.12.104

  日期：2007.3

  A novel series of 3-substituted-8-aryl-[1,2,4]-triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A(2A) receptor antagonists with improved selectivity over the A(1) receptor, physiochemical properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound 27 displayed both superior in vitro and highly promising in vivo profiles. (c) 2007 Elsevier Ltd. All rights reserved.