6-α-N-ethylcarbamoylethylthio-4-methylthio-1-phenylpyrazolo[3,4-d]pyrimidine | 159256-65-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-α-N-ethylcarbamoylethylthio-4-methylthio-1-phenylpyrazolo[3,4-d]pyrimidine
• 英文别名: N-ethyl-2-(4-methylsulfanyl-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl)sulfanylpropanamide
• CAS: 159256-65-2
• 化学式: C₁₇H₁₉N₅OS₂
• 分子量: 373.503
• InChiKey: ZMEKXRKHLRBQGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-α-N-ethylcarbamoylethylthio-4-methylthio-1-phenylpyrazolo[3,4-d]pyrimidine 在 氨 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以79%的产率得到2-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl)sulfanyl-N-ethylpropanamide
  参考文献：
  名称：

  1-Phenylpyrazolo[3,4- d ]pyrimidines; structure–activity relationships for C6 substituents at A 1 and A 2A adenosine receptors

  摘要：

  Substitution of 1-phenylpyrazolo[3,4-d]pyrimidines at C6 with N-alkyl-2-thiopropionamide groups has resulted in a series of 18 compounds which have been evaluated for binding at A(1) and A(2A) adenosine receptors. introduction of an N-ethyl group gave increased affinity at both A(1) and A(2A) receptors for the amino compound 7b compared to the primary amide 7a. An additional hydrophobic pocket exists for substituents on the amide. This pocket allows an N-ethyl group for increased affinity at both A(1) and A(2A) receptors, allows larger alkyl groups at A(2A) receptors but not at A(1) receptors and there is an H-bond interaction requiring one H-bond donor. Molecular modeling studies have also enabled a proposal of the amino acid residues involved in ligand binding at both the A(1) and A(2A) receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00190-5
• 作为产物：
  描述：

  1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 反应 3.5h， 生成 6-α-N-ethylcarbamoylethylthio-4-methylthio-1-phenylpyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  1-Phenylpyrazolo[3,4- d ]pyrimidines; structure–activity relationships for C6 substituents at A 1 and A 2A adenosine receptors

  摘要：

  Substitution of 1-phenylpyrazolo[3,4-d]pyrimidines at C6 with N-alkyl-2-thiopropionamide groups has resulted in a series of 18 compounds which have been evaluated for binding at A(1) and A(2A) adenosine receptors. introduction of an N-ethyl group gave increased affinity at both A(1) and A(2A) receptors for the amino compound 7b compared to the primary amide 7a. An additional hydrophobic pocket exists for substituents on the amide. This pocket allows an N-ethyl group for increased affinity at both A(1) and A(2A) receptors, allows larger alkyl groups at A(2A) receptors but not at A(1) receptors and there is an H-bond interaction requiring one H-bond donor. Molecular modeling studies have also enabled a proposal of the amino acid residues involved in ligand binding at both the A(1) and A(2A) receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00190-5

文献信息

• Pyrazolo[3,4-d]pyrimidines with adenosine-like binding affinities
  申请人：Griffith University

  公开号：US05227485A1

  公开（公告）日：1993-07-13

  The A21 receptor extracelluar site and the A2 receptor extracellular site of adenosine analogues are structurally different and that binding orientations of adenosine or adenosine analogues are different at these sites and this may be used to determine their structure. Novel pyrimidine compounds are described.

  A21受体细胞外位点和A2受体细胞外位点的腺苷类似物在结构上不同，并且腺苷或腺苷类似物在这些位点的结合取向不同，这可以用来确定它们的结构。描述了新型嘧啶化合物。
• US5227485A
  申请人：——

  公开号：US5227485A

  公开（公告）日：1993-07-13
• 1-Phenylpyrazolo[3,4- d ]pyrimidines; structure–activity relationships for C6 substituents at A 1 and A 2A adenosine receptors
  作者：Mary Chebib、Declan McKeveney、Ronald J. Quinn

  DOI：10.1016/s0968-0896(00)00190-5

  日期：2000.11

  Substitution of 1-phenylpyrazolo[3,4-d]pyrimidines at C6 with N-alkyl-2-thiopropionamide groups has resulted in a series of 18 compounds which have been evaluated for binding at A(1) and A(2A) adenosine receptors. introduction of an N-ethyl group gave increased affinity at both A(1) and A(2A) receptors for the amino compound 7b compared to the primary amide 7a. An additional hydrophobic pocket exists for substituents on the amide. This pocket allows an N-ethyl group for increased affinity at both A(1) and A(2A) receptors, allows larger alkyl groups at A(2A) receptors but not at A(1) receptors and there is an H-bond interaction requiring one H-bond donor. Molecular modeling studies have also enabled a proposal of the amino acid residues involved in ligand binding at both the A(1) and A(2A) receptors. (C) 2000 Elsevier Science Ltd. All rights reserved.