2-(4-氨基咪唑并[5,4-d]三嗪-7-基)-5-(羟基甲基)四氢呋喃-3,4-二醇 | 146-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(4-氨基咪唑并[5,4-d]三嗪-7-基)-5-(羟基甲基)四氢呋喃-3,4-二醇
• 中文别名: 2-氮杂腺苷
• 英文名称: 2-Azaadenosine
• 英文别名: 4-amino-7-(β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazine；1-(4-amino-imidazo[4,5-d][1,2,3]triazin-7-yl)-β-D-1-deoxy-ribofuranose；2-Azaadenosin；(2R,3R,4S,5R)-2-(4-aminoimidazo[4,5-d]triazin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 146-94-1
• 化学式: C₉H₁₂N₆O₄
• 分子量: 268.232
• InChiKey: JNGWKCBNKZBPLB-UUOKFMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(4-氨基咪唑并[5,4-d]三嗪-7-基)-5-(羟基甲基)四氢呋喃-3,4-二醇 在 溴 、 sodium acetate 作用下， 以 水 为溶剂， 反应 75.0h， 生成 4-amino-6-bromo-7-(β-D-ribofuranosyl)imidazo[4,5-d]-v-triazine
  参考文献：
  名称：

  Purine nucleoside analogues for treating flaviviridae including hepatitis C

  摘要：

  这项发明涉及一种治疗宿主，特别是感染丙型肝炎、黄病毒和/或猪瘟病毒的方法，包括向该宿主施用一种抗HCV生物活性的戊呋喃核苷的有效量，其中戊呋喃核苷的碱基是一种可选择取代的2-氮杂嘌呤。可选择取代的戊呋喃核苷，或其盐或前药，可以单独或与一个或多个可选择取代的戊呋喃核苷或其他抗病毒药剂联合使用。

  公开号：

  US09186369B2
• 作为产物：
  描述：

  2',3',5'-tri-O-(acetyl)-2-azainosine 在 氨 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 76.5h， 生成 2-(4-氨基咪唑并[5,4-d]三嗪-7-基)-5-(羟基甲基)四氢呋喃-3,4-二醇
  参考文献：
  名称：

  Synthesis of 4-Substituted Imidazo[4,5-d][1,2,3]triazine (2-Azapurine)nucleosides

  摘要：

  Several methods for functionalization of the 4-position of imidazo[4,5-d][1,2,3]triazin-4-one were investigated. These investigations were successful and led to the preparation of 4-amino, 4-triazol-1-yl, 4-methoxy, 4-methylthio, 4-methylamino, 4-thio, 4-nitrobenzyl, and 4-unsubstituted 9-(beta-D-ribofuranosyl)-imidazo-[4,5-d][1,2,3]triazine (2-azapurine ribosides). The 4-unsubstituted compound (19) was slightly active against HCMV in plaque and yield reduction experiments and was not cytotoxic at 100 mu M. The methylamino (15), hydrazino (16), and p-nitrobenzylthio (20) were inactive against HCMV but slightly cytotoxic. The thiomethyl-substituted analog (21) was the most active with activity comparable to ganciclovir but with greater cytotoxicity. We conclude that even though none of the tested compounds had antiviral activity superior to ganciclovir, the new synthetic methods will provide a route to more interesting compounds.

  DOI：

  10.1080/15257770008032996

文献信息

• Purine nucleoside analogues for treating Flaviviridae including hepatitis C
  申请人：Storer Richard

  公开号：US20050075309A1

  公开（公告）日：2005-04-07

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside where the pentofuranonucleoside base is an optionally substituted 2-azapurine. The optionally substituted pentofuranonucleoside, or a salt or prodrug thereof, may be administered alone or in combination with one or more optionally substituted pentofuranonucleosides or other anti-viral agents.

  本发明涉及一种治疗宿主，尤其是感染丙型肝炎病毒、黄热病毒和/或猪瘟病毒的人类的方法，包括向该宿主施用有效量的抗HCV生物活性五元糖基噻唑核苷，其中五元糖基噻唑核苷基是一个可选取代的2-氮杂嘌呤。可选取代的五元糖基噻唑核苷，或其盐或前药，可以单独或与一个或多个可选取代的五元糖基噻唑核苷或其他抗病毒药物联合使用。
• 2-azapurine compounds and their uses
  申请人：Seela Frank

  公开号：US20070015725A1

  公开（公告）日：2007-01-18

  Within oligonucleotides 2-azapurine and especially 2-azaadenine bases form specifically base pairs with guanine. This base pair is of analogous stability as an adenine-thymine but less stable than a guanine-cytosine base pair. Therefore, the incorporation of 2-azaadenine residues into oligonucleotides instead of cytosine leads specifically to hybridization complexes with nucleic acids with homogenous stability. This is useful for the adaptation of the stabilities of different oligonucleotide sequences in all kinds of hybridization techniques, for example in oligomer chip technology.

  在寡核苷酸内，2-氮杂嘌呤尤其是2-氮杂腺嘌呤碱基与鸟嘌呤形成特异性碱基对。这种碱基对的稳定性类似于腺嘌呤-胸腺嘧啶，但不如鸟嘌呤-胞嘧啶碱基对稳定。因此，将2-氮杂腺嘌呤残基纳入寡核苷酸中，而不是胞嘧啶，导致与同种稳定性的核酸形成特异性杂交复合物。这对于在各种杂交技术中适应不同寡核苷酸序列的稳定性非常有用，例如在寡聚物芯片技术中。
• Purine nucleoside analogues for treating flaviviridae including hepatitis C
  申请人：Storer Richard

  公开号：US08742101B2

  公开（公告）日：2014-06-03

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside where the pentofuranonucleoside base is an optionally substituted 2-azapurine. The optionally substituted pentofuranonucleoside, or a salt or prodrug thereof, may be administered alone or in combination with one or more optionally substituted pentofuranonucleosides or other anti-viral agents.

  本发明涉及一种治疗感染丙型肝炎病毒、黄热病毒和/或猪瘟病毒的宿主，尤其是人类的方法，包括向该宿主施用一种有效量的抗HCV生物活性戊呋喃核苷，其中戊呋喃核苷碱基为可选取代的2-氮杂嘌呤。该可选取代的戊呋喃核苷，或其盐或前药，可以单独或与一个或多个可选取代的戊呋喃核苷或其他抗病毒药物联合使用。
• PURINE NUCLEOSIDE ANALOGUES FOR TREATING FLAVIVIRIDAE INCLUDING HEPATITIS C
  申请人：Indenix Pharmaceuticals, Inc.

  公开号：US20140234251A1

  公开（公告）日：2014-08-21

  This invention is directed to a method for treating a host, especially a human, infected with hepatitis C, flavivirus and/or pestivirus, comprising administering to that host an effective amount of an anti-HCV biologically active pentofuranonucleoside where the pentofuranonucleoside base is an optionally substituted 2-azapurine. The optionally substituted pentofuranonucleoside, or a salt or prodrug thereof, may be administered alone or in combination with one or more optionally substituted pentofuranonucleosides or other anti-viral agents.

  这项发明涉及一种治疗感染丙型肝炎病毒、黄热病毒和/或猪瘟病毒的宿主，特别是人类的方法，包括向该宿主施用一种抗HCV生物活性戊呋喃核苷，其中戊呋喃核苷碱基是一个可选择取代的2-氮杂嘌呤。可选择取代的戊呋喃核苷，或其盐或前药，可以单独或与一个或多个可选择取代的戊呋喃核苷或其他抗病毒药物联合使用。
• Purinyl cyclobutanes
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0322854A1

  公开（公告）日：1989-07-05

  Antiviral activity is exhibited by compounds having the formula and pharmaceutically acceptable salts thereof wherein R2 and R3 are independently hydrogen, -P03H2 or and R1 is either a purine, pyrimidine or an analog thereof.

  具有以下式子的化合物具有抗病毒活性 及其药学上可接受的盐类，其中 R2 和 R3 独立地是氢、-P03H2 或 而 R1 是嘌呤、嘧啶或其类似物。