1H-吡唑并[3,4-D]嘧啶-4,6-二胺 | 5413-80-9

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 中文名称: 1H-吡唑并[3,4-D]嘧啶-4,6-二胺
• 中文别名: 4,6-二氨基-1H-吡唑[3,4-D]嘧啶；1(H)-4,6-二氨基吡唑【3,4-D】嘧啶；1H-吡唑并[3,4-d]嘧啶-4,6-二胺
• 英文名称: 2,4-Diamino-7H-pyrazolo<3,4-d>pyrimidine
• 英文别名: 4,6-Diaminopyrazolo<3,4-d>pyrimidine；1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine；4,6-diaminopyrazolo(3,4-d)pyrimidine；8-aza-7-deaza-2,6-diaminopurine；8-aza-7-deazapurine-4,6-diamine；1(2)H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• CAS: 5413-80-9
• 化学式: C₅H₆N₆
• 分子量: 150.143
• InChiKey: NXSAXOJMBFFHSG-UHFFFAOYSA-N

物化性质

• 熔点：
  291 °C(Solv: water (7732-18-5))
• 沸点：
  302.1±52.0 °C(Predicted)
• 密度：
  2.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338,P310
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  1H-吡唑并[3,4-D]嘧啶-4,6-二胺 在 三氟化硼乙醚 甲醇 、 N-碘代丁二酰亚胺 、 sodium methylate 作用下， 以 硝基甲烷 、 1,2-二氯乙烷 为溶剂， 生成 3-iodo-1-(β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
  参考文献：
  名称：

  7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.

  DOI：

  10.1081/ncn-200059218
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 氨 作用下， 生成 1H-吡唑并[3,4-D]嘧啶-4,6-二胺
  参考文献：
  名称：

  Robins, Journal of the American Chemical Society, 1957, vol. 79, p. 6407,6412

  摘要：

  DOI：

文献信息

• Recognition of Artificial Nucleobases by<i>E. coli</i>Purine Nucleoside Phosphorylase versus its Ser90Ala Mutant in the Synthesis of Base-Modified Nucleosides
  作者：Ilja V. Fateev、Maria I. Kharitonova、Konstantin V. Antonov、Irina D. Konstantinova、Vasily N. Stepanenko、Roman S. Esipov、Frank Seela、Kartik W. Temburnikar、Katherine L. Seley-Radtke、Vladimir A. Stepchenko、Yuri A. Sokolov、Anatoly I. Miroshnikov、Igor A. Mikhailopulo

  DOI：10.1002/chem.201501334

  日期：2015.9.14

  mechanism of recognition by the wild‐type (WT) E. coli purine nucleoside phosphorylase (PNP) versus its Ser90Ala mutant. The results were analyzed from viewpoint of the role of the Ser90 residue and the structural features of the bases. It was found that the Ser90 residue of the PNP 1) plays an important role in the binding and activation of 8‐aza‐7‐deazapurines in the synthesis of their nucleosides, 2) participates

  广泛的天然嘌呤类似物用作探针，以评估野生型（WT）大肠杆菌嘌呤核苷磷酸化酶（PNP）与其Ser90Ala突变体的识别机制。从Ser90残基的作用和碱基的结构特征的角度分析了结果。发现PNP的Ser90残基在其核苷合成中的8-氮杂-7-脱氮嘌呤的结合和活化中起重要作用; 2）参与α - D-戊呋喃糖-1的结合。在PNP的催化位点处的磷酸，以及3）催化中间形成的2-deoxy-α- D的去磷酸化反式2-脱氧核糖基化反应中的核糖呋喃糖-1-磷酸。5-氮杂-7-脱氮鸟嘌呤对两种酶均表现出优异的底物活性，8-氨基-7-硫杂鸟嘌呤和2-氨基苯并噻唑对两种酶均无底物活性。相反，苯并咪唑和苯并恶唑的2-氨基衍生物是底物，分别被转化为N1-糖苷和不寻常的N2-糖苷。9-Deaza-5-碘黄嘌呤对野生型大肠杆菌PNP具有中等抑制活性，而9-deazaxanthine及其2'-脱氧核糖苷是弱抑制剂。
• Pyrazolo[3,4-d]pyrimidine ribonucleosides related to 2-aminoadenosine and isoguanosine: synthesis, deamination and tautomerism
  作者：Frank Seela、Kuiying Xu

  DOI：10.1039/b708736e

  日期：——

  than that of the related purines. The pK(a) values indicate that the 7-non-functionalized nucleosides 1a (pK(a) 5.8) and 15 (pK(a) 6.4) are possibly protonated in neutral conditions when incorporated into RNA. The nucleosides 3a-d exist predominantly in the keto (lactam) form with K(TAUT) (keto/enol) values of 400-1200 compared to 10(3)-10(4) for pyrrolo[2,3-d]pyrimidine isoguanosine derivatives 4a-c

  描述了与2-氨基腺苷和异鸟苷相关的8-氮杂-7-脱氮嘌呤（吡唑并[3,4-d]嘧啶）核糖核苷的合成和性质。在BF（3）存在下，将1-氮-乙酰基2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖与8-氮杂7-脱氮嘌呤-2,6-二胺5糖基化。 ）x Et（2）O作为催化剂，得到N（8）异构体14（73％）和痕量的N（9）异构体13a（4.8％）。在相同的反应条件下，7-卤代8-氮杂-7-脱氮嘌呤-2,6-二胺6-8提供了热力学上更稳定的N（9）核苷13b-d作为唯一产物（53-70％）。因此，位置7的卤素将糖基化作用从N（8）转移到N（9）。通过2-氨基的重氮化将8-氮杂-7-脱氮嘌呤-4，6-二胺核糖核苷1a-d转化为异鸟苷衍生物3a-d。尽管化合物1a b。在7位（酶结合位点）不含氮，它们被腺苷脱氨酶脱氨；但是，它们的脱氨速度比相关嘌呤的速度要慢得多。pK（a）值表明，将7个非功能化核苷1a（pK（a）5
• Influence of PNA containing 8-aza-7-deazaadenine on structure stability and binding affinity of PNA·DNA duplex: insights from thermodynamics, counter ion, hydration and molecular dynamics analysis
  作者：Sharad K. Gupta、Souvik Sur、Rajendra Prasad Ojha、Vibha Tandon

  DOI：10.1039/c3mb25561a

  日期：——

  This paper describes the synthesis of a novel 8-aza-7-deazapurin-2,6-diamine (DPP)-containing peptide nucleic acid (PNA) monomer and Boc protecting group-based oligomerization of PNA, replacing adenine (A) with DPP monomers in the PNA strand. The PNA oligomers were synthesized against the biologically relevant SV40 promoter region (2494-AATTTTTTTTATTTA-2508) of pEGFP-N3 plasmid. The DPP-PNA.DNA duplex

  本文介绍了新型的含8-氮杂7-脱氮嘌呤-2,6-二胺（DPP）的肽核酸（PNA）单体的合成以及基于Boc保护基的PNA的低聚反应，用DPP取代了腺嘌呤（A） PNA链中的单体。针对pEGFP-N3质粒的生物学相关SV40启动子区域（2494-AATTTTTTTTATTATTTA-2508），合成了PNA寡聚物。与正常双链体（A-PNA.DNA）相比，DPP-PNA.DNA双链体显示出增强的稳定性。DPP单体的电子分布表明，DPP具有比2,6-二氨基嘌呤更好的电子给体性能。紫外熔融和热力学分析表明，与A-PNA.DNA相比，含有二氨基吡唑并（3,4-d）嘧啶部分（DPP）的PNA低聚物稳定了PNA.DNA杂种。DPP-PNA.DNA双链体显示出更高的水活度（Deltanw = 38。5）与A-PNA.DNA双链体相比（Deltanw = 14.5）。含有DPP或未修饰核碱基-A的PNA.DNA双链体的50
• Synthesis of pyrazolo 3,4-pyrimidine analogues of the potent agent N-4-2-2-amino-4 3-oxo-7-pyrrolo 2,3-pyrimidin-5-yl ethylbenzoyl-L-glutamic acid (LY231514)
  作者：Edward C. Taylor、Hemantkumar H. Patel

  DOI：10.1016/s0040-4020(01)80479-8

  日期：1992.1

  Several pyrazolo[3,4-d]pyrimidine analogues of the potent antitumor agent N-4-12-(2-amino-4(3H)-oxo-7H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid (LY231514, 5) have been prepared. A principal synthetic step proved to be a palladium-catalyzed C-C coupling of the 5-halo-substituted pyrazolo[3,4-d]pyrimidines 12-15 with dimethyl 4-ethynylbenzoyl-L-glutamate (16). An additional pyrazolo[3,4-d]pyrimidine analogue of 5 possessing an isofolic acid bridge unit (-NHCH2-) was prepared by reductive alkylation of diethyl 4-formylbenzoyl-L-glutamate (31) with 2-methyl-5-amino-4(3H)-oxo-7H-pyrazolo[3,4-d]pyrimidine (30). Only compound 26 proved to have in vitro cell growth inhibitory activity.
• Gatta; Gradoni; Lupardini, Il Farmaco, 1991, vol. 46, # 1, p. 75 - 84
  作者：Gatta、Gradoni、Lupardini、Gramiccia、Orsini

  DOI：——

  日期：——