3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine | 356038-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• 英文别名: 3-Bromo-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1H-pyrazolo(3,4-d)pyrimidine-4,6-diamine；(2R,3S,5R)-5-(4,6-diamino-3-bromopyrazolo[3,4-d]pyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 356038-31-8
• 化学式: C₁₀H₁₃BrN₆O₃
• 分子量: 345.156
• InChiKey: IEWQVRVPSMDYDF-VPENINKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  145
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 在 溶剂黄146 、 sodium nitrite 作用下， 生成 diphenyl-carbamic acid 1-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-3-bromo-4-(dimethylamino-methyleneamino)-1H-pyrazolo[3,4-d]pyrimidin-6-yl ester
  参考文献：
  名称：

  PARALLEL DNA CONTAINING PYRAZOLO[3,4-D]PYRIMIDINE ANALOGUES OF ISOGUANINE

  摘要：

  The phosphoramidites of 8-aza-7-deaza-2'-deoxyisoguanosine (1a) and its bromo derivative 1b as well as of 6-aza-2-deoxyisocytidine and its 5-methyl derivative (3a,b) were synthesized. Parallel-stranded duplexes containing the nucleosides 1a,b show a significantly enhanced duplex stability compared to those containing 2'-deoxyisoguanosine.

  DOI：

  10.1081/ncn-100002537
• 作为产物：
  描述：

  (2R,3S,5R)-5-(6-amino-3-bromo-4-propan-2-yloxypyrazolo[3,4-d]pyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-ol 在 氨 作用下， 以 水 为溶剂， 生成 3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
  参考文献：
  名称：

  10.1081/ncn-120021957

  摘要：

  DOI：

  10.1081/ncn-120021957

文献信息

• Nucleic acid binding compounds containing pyrazolo[3,4-d]pyrimidine analogues of purin-2,6-diamine and their uses
  申请人：——

  公开号：US20030198982A1

  公开（公告）日：2003-10-23

  The present invention is in the field of nucleic acid binding compounds comprising 7-substituted 7-deaza-8aza-2,6-diamino-purine bases, compounds useful for the preparation of such compounds, various uses thereof and methods for the determination of nucleic acids using said compounds in the field of diagnostics.

  本发明涉及核酸结合化合物领域，包括7-取代7-脱氮-8-脱氮-2,6-二氨基嘌呤碱基的化合物，用于制备此类化合物的化合物，它们的各种用途以及在诊断领域中使用该化合物进行核酸测定的方法。
• Major-Groove-Halogenated DNA: The Effects of Bromo and Iodo Substituents Replacing H−C(7) of 8-Aza-7-deazapurine-2,6-diamine or H−C(5) of Uracil Residues
  作者：Georg Becher、Junlin He、Frank Seela

  DOI：10.1002/1522-2675(20010516)84:5<1048::aid-hlca1048>3.0.co;2-9

  日期：2001.5.16

  counterparts containing 2′-deoxyadenosine, the purine-2,6-diamine 2′-deoxyribonucleoside (1), or 2a at the same positions. Six 2b residues replacing dA in the duplex 5′-d(TAGGTCAATACT)-3′ (11)⋅5′-d(AGTATTGACCTA)-3′ (12) raised the Tm value from 48 to 75° (4.5° per modification (Table 3)). Contrary to this, incorporation of the 5-halogenated 2′-deoxyuridines 3b or 3c into oligonucleotide duplexes showed very

  合成了含有卤代“嘌呤”和嘧啶碱基的寡核苷酸。溴和碘取代基被引入 8-aza-7-deazapurine-2,6-二胺的 7 位（见 2b,c）或尿嘧啶残基的 5 位（见 3b,c）。在用异丁酰基保护2b和用苯甲酰基保护2c后合成亚磷酰胺。含有残基 2b 或 2c 的双链体的 Tm 值总是高于在相同位置含有 2'-脱氧腺苷、嘌呤-2,6-二胺 2'-脱氧核糖核苷 (1) 或 2a 的未修饰对应物的 Tm 值。六个 2b 残基取代双链体 5'-d(TAGGTCAATACT)-3' (11)⋅5'-d(AGTATTGACCTA)-3' (12) 中的 dA 将 Tm 值从 48 提高到 75°（每次修饰 4.5°（表3））。与此相反，将 5-卤代 2'-脱氧尿苷 3b 或 3c 掺入寡核苷酸双链体中对热稳定性的影响很小，无论哪个“嘌呤”核苷位于它们对面（表 4 和表 5）。对 DNA 中观察到的双链体热稳定性的积极影响也在
• Nucleic acid binding compounds containing pyrazolo[3,4-D]pyrimidine analogues of purin-2,6-diamine and their uses
  申请人：Roche Molecular Systems, Inc.

  公开号：US08057997B2

  公开（公告）日：2011-11-15

  The present invention is in the field of nucleic acid binding compounds comprising 7-substituted 7-deaza-8aza-2,6-diamino-purine bases, compounds useful for the preparation of such compounds, various uses thereof and methods for the determination of nucleic acids using said compounds in the field of diagnostics.

  本发明涉及核酸结合化合物领域，包括7-取代基7-脱氮-8-氮杂-2,6-二氨基嘌呤碱基的化合物，用于制备此类化合物的化合物，它们的各种用途以及在诊断领域中使用这些化合物进行核酸测定的方法。
• Nucleic Acid Binding Compounds Containing Pyrazolo[3,4-D]Pyrimidine Analogues of Purin-2,6-Diamine and Their Uses
  申请人：Seela Frank

  公开号：US20110021365A1

  公开（公告）日：2011-01-27

  The present invention is in the field of nucleic acid binding compounds comprising 7-substituted 7-deaza-8aza-2,6-diamino-purine bases, compounds useful for the preparation of such compounds, various uses thereof and methods for the determination of nucleic acids using said compounds in the field of diagnostics.

  本发明涉及核酸结合化合物领域，包括7-取代7-脱氧-8-氮杂-2,6-二氨基嘌呤碱基的化合物，用于制备此类化合物的化合物，其各种用途以及在诊断领域中使用该化合物确定核酸的方法。
• NUCLEIC ACID BINDING COMPOUNDS CONTAINING PYRAZOLO[3,4-D]PYRIMIDINE ANALOGUES OF PURIN-2,6-DIAMINE AND THEIR USES
  申请人：Roche Diagnostics GmbH

  公开号：EP1307469A1

  公开（公告）日：2003-05-07