1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione | 6289-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione
• 英文别名: 1-phenyl-5H,7H-pyrazolo<3,4-d>pyrimidine-4,6-dithione；1-phenylpyrazolo<3,4-d>pyrimidine-4,6(5H,7H)-dithione；1-Phenyl-5H,7H-pyrazolo<3,4-d>pyrimidin-4,6-dithion；1-Phenyl-5H,7H-pyrazolo<3,4-d>pyrimidindithion-(4,6)；1-Phenyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidin-4,6-dithion；1-phenyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dithione；1-Phenyl-5H,7H-pyrazolo[3,4-d]pyrimidin-4,6-dithione；1H-Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione, 1-phenyl-；1-phenyl-7H-pyrazolo[3,4-d]pyrimidine-4,6-dithione
• CAS: 6289-02-7
• 化学式: C₁₁H₈N₄S₂
• 分子量: 260.343
• InChiKey: CQTGWNDHFQMIGD-UHFFFAOYSA-N

物化性质

• 熔点：
  230-232 °C
• 沸点：
  446.7±37.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 α-(4-methylthio-1-phenylpyrazolo<3,4-d>pyrimidin-6-ylthio)propionamide
  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：

  苯肼 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione
  参考文献：
  名称：

  氨基氰基吡唑合成新型吡唑并嘧啶二硫酮和吡唑并嘧啶膦

  摘要：

  摘要 提出了一种从氨基-氰基吡唑 1 前体快速合成官能化吡唑并嘧啶二硫酮 2 和吡唑二氮杂膦硫酮 3 的通用、高产合成方案。

  DOI：

  10.1080/00397911.2010.486516

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。
• Synthesis and Structure−Activity Relationship of Pyrazolo[3,4-<i>d</i>]pyrimidines:  Potent and Selective Adenosine A₁ Receptor Antagonists
  作者：Sally-Ann Poulsen、Ronald J. Quinn

  DOI：10.1021/jm960052s

  日期：1996.1.1

  structural differences between the A1 and A2a receptors with respect to the binding of pyrazolo[3,4-d]pyrimidines. This study resulted in prediction that increased A1 affinity could be achieved by incorporation of NH-alkyl substituents at C-4. This was confirmed by synthesis of alpha-[[4-(methylamino)-1-phenylpyrazolo[3,4-d]pyrimidin-6-yl]thiol] hexanamide (15) which was found to have an A1 Ki of 0.745 nM

  合成一系列12个取代的1-苯基吡唑并[3,4-d]嘧啶并评估其对大鼠脑腺苷A1和A2a受体的结合亲和力。为了在受体亚型的分子识别方面定义这些区域，改变了C-4和C-6处的取代基。在C-4处，评估了巯基，甲硫基和氨基取代基的作用，而在C-6处，研究了具有从α-碳延伸的烷基的酰胺。这项研究确定了有效和选择性的腺苷A1受体拮抗剂。在这12种化合物中，最有效的化合物是α-[（4-氨基-1-苯基吡唑并[3,4-d]嘧啶-6-基）硫基]己酰胺（14）；该化合物的A1 Ki为0.939 nM，A2a Ki为88.3 nM，是A1选择性的94倍。在这12种化合物中，选择性最高的是α-[[4-（甲硫基）-1-苯基吡唑并[3，4-d]嘧啶-6-基]硫代]己酰胺（10）; 如果A1 Ki为6.81 nM，A2a Ki> 40 000 nM，则该化合物对A1的选择性是> 5900倍。完整系列的结构-活性关系已确定在吡唑并[3
• 1-Phenylpyrazolo[3,4-d]pyrimidines as adenosine antagonists: the effects of substituents at C4 and C6
  作者：Mary Chebib、Ronald J. Quinn

  DOI：10.1016/s0968-0896(96)00240-4

  日期：1997.2

  Forty-two 1-phenyl-pyrazolo[3,4-d]pyrimidines substituted at C6 with thioethers containing distal amide substituents and substituted at C4 with thiol, thiomethyl or amino were synthesized and tested for adenosine A(1) and A(2a) receptor binding. Compared with a thiol at C4, both S-methylation and conversion to an amino resulted in increased affinity at both receptors with the C4 amino compounds having the highest affinity. The C-4 region of the receptor consists of an alkyl pocket containing a hydrogen-bonding site. The study established that for high affinity at both the A(1) and A(2a) adenosine receptors the distal amide should be separated from the C6 thiol by only one carbon. In this study, 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)- N-ethyl-ethanamide (4b) had the highest affinity at the A(1) receptor with a K-i of 12.1 nM while 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)ethanamide (4a) had the highest affinity at the A(2a) receptor with a K-i of 44.9 nM. (C) 1997, Elsevier Science Ltd.
• Pyrazolo[3,4-d]pyrimidines: C4, C6 substitution leads to adenosine A1 receptor selectivity
  作者：Sally-Ann Poulsen、Ronald J. Quin

  DOI：10.1016/0960-894x(96)00027-3

  日期：1996.2

  Following the demonstration that substitution of 1-phenylpyrazolo[3,4-d]pyrimidines at C6 with thioethers containing amide moieties could effect adenosine A(1) and A(2a) receptor selectivity, two compounds with high A(1) selectivity have been obtained by a combined C4, C6 substitution. This further demonstrates that distal moieties at C6 can effect selectivity and that C4 substitutents have an important role.
• 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：——