2-(4-氨基-1-苯基-1H-吡唑并[3,4-d]嘧啶-6-基硫烷基)丙酰胺 | 134896-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氨基-1-苯基-1H-吡唑并[3,4-d]嘧啶-6-基硫烷基)丙酰胺
• 英文名称: α-(4-amino-1-phenylpyrazolo<3,4-d>pyrimidin-6-ylthio)propionamide
• 英文别名: 4-amino-6-α-carbamoylethylthio-1-phenylpyrazolo[3,4-d]dipyrimidine；GU285；Propanamide, 2-((4-amino-1-phenyl-1H-pyrazolo(3,4-d)pyrimidin-6-yl)thio)-；2-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl)sulfanylpropanamide
• CAS: 134896-40-5
• 化学式: C₁₄H₁₄N₆OS
• 分子量: 314.371
• InChiKey: LCRKMFXRXUTCIM-UHFFFAOYSA-N

物化性质

• 熔点：
  284-286 °C(Solv: dimethyl sulfoxide (67-68-5))
• 沸点：
  568.1±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione 在 sodium hydroxide 、 氨 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 75.5h， 生成 2-(4-氨基-1-苯基-1H-吡唑并[3,4-d]嘧啶-6-基硫烷基)丙酰胺
  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

• Quinn, Ronald J.; Scammells, Peter J.; Tucker, David J., Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 753 - 757
  作者：Quinn, Ronald J.、Scammells, Peter J.、Tucker, David J.

  DOI：——

  日期：——
• QUINN, RONALD J.;SCAMMELLS, PETER J.;TUCKER, DAVID J., AUSTRAL. J. CHEM., 44,(1991) N, C. 753-757
  作者：QUINN, RONALD J.、SCAMMELLS, PETER J.、TUCKER, DAVID J.

  DOI：——

  日期：——
• 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.