2-azainosine | 36519-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azainosine
• 英文别名: 2-Azainosin；2-Azainosine；7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-imidazo[4,5-d]triazin-4-one
• CAS: 36519-16-1
• 化学式: C₉H₁₁N₅O₅
• 分子量: 269.217
• InChiKey: LSMBOEFDMAIXTM-UUOKFMHZSA-N

物化性质

• 沸点：
  717.4±70.0 °C(Predicted)
• 密度：
  2.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 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：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azainosine 在 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-methylamino-7-[2,3,5-tri-O-(t-butyldimethylsilyl)-β-D-ribofuranosyl]imidazo[4,5-d][1,2,3]triazine
  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
• 作为产物：
  描述：

  阿卡地新 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 2.58h， 生成 2-azainosine
  参考文献：
  名称：

  [EN] CYCLIC DINUCLEOTIDE COMPOUNDS CONTAINING 2-AZA-HYPOXANTHINE OR 6H-PYTAZOLO[1,5-D][1,2,4]TRIAZIN-7-ONE AS STING AGONISTS
  [FR] COMPOSÉS DINUCLÉOTIDIQUES CYCLIQUES CONTENANT 2-AZA-HYPOXANTHINE OU 6H-PYTAZOLO[1,5-D][1,2,4]TRIAZINE-7-ONE EN TANT QU'AGONISTES DE STING

  摘要：

  式I的化合物，其中Base、R1和R2的定义如权利要求1中所述，是STING的调节剂。

  公开号：

  WO2019185477A1

文献信息

• Purine nucleoside analogues for treating flaviviridae including hepatitis C
  申请人：Idenix Pharmaceuticals, Inc.

  公开号：US09186369B2

  公开（公告）日：2015-11-17

  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。
• Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes
  作者：Kazutada Ikeuchi、Ryosuke Fujii、Shimpei Sugiyama、Tomohiro Asakawa、Makoto Inai、Yoshitaka Hamashima、Jae-Hoon Choi、Tomohiro Suzuki、Hirokazu Kawagishi、Toshiyuki Kan

  DOI：10.1039/c4ob00705k

  日期：——

  AHX derivatives and their probe molecules.

  AHX衍生物及其探针分子。
• Preparation of oligonucleotides containing dAICA using an unexpected side-reaction observed on a protected derivative of 2-aza-2′-deoxyinosine.
  作者：Dolors Fernandez-Forner、Ramon Eritja、Francesc Bardella、Catalina Ruiz-Perez、Xavier Solans、Ernest Giralt、Enrique Pedroso

  DOI：10.1016/s0040-4020(01)81004-8

  日期：1991.10

  Attempts of synthesis of oligonucleotides containing 2-aza-2′-deoxyinosine protected with the N,N-diphenylcarbamoyl group are described. An unexpected behaviour of the protected nucleoside can be used for the introduction of dAICA in synthetic oligonucleotides.

  描述了合成包含被N，N-二苯基氨基甲酰基保护的2-氮杂-2'-脱氧肌苷的寡核苷酸的尝试。受保护核苷的意外行为可用于在合成寡核苷酸中引入dAICA。
• 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。
• 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。