2',3',5'-tri-O-(acetyl)-2-azainosine | 36519-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',3',5'-tri-O-(acetyl)-2-azainosine
• 英文别名: 7-(2,3,5,-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazin-4-one；7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one；7-(tri-O-acetyl-β-D-ribofuranosyl)-3,7-dihydro-imidazo[4,5-d][1,2,3]triazin-4-one；7-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)imidazo[4,5-d]-v-triazin-4-one；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-oxo-3H-imidazo[4,5-d]triazin-7-yl)oxolan-2-yl]methyl acetate
• CAS: 36519-17-2
• 化学式: C₁₅H₁₇N₅O₈
• 分子量: 395.329
• InChiKey: JKAKQPGSRIYHDO-SDBHATRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  160
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(acetyl)-2-azainosine 在 sodium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.5h， 生成 4-(N,N-diethylamino)-7-(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 吡啶 、 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 18.0h， 生成 2',3',5'-tri-O-(acetyl)-2-azainosine
  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

文献信息

• 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。
• 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。
• Synthesis and Biophysical and Biological Properties of Oligonucleotides Containing 2-Aza-2'-Deoxyinosine
  作者：Montse Acedo、Erik De Clercq、Ramon Eritja

  DOI：10.1021/jo00125a009

  日期：1995.10

  The preparation of oligonucleotides containing 2-aza-2'-deoxyinosine is described. Protection of the 2-azahypoxanthine moiety with the photolabile 2-nitrobenzyl group enabled us to obtain the phosphoramidite derivative and oligonucleotides containing protected 2-aza-2'-deoxyinosine. After purification, photolysis of the oligonucleotides containing the protected analogue provided the desired oligonucleotides in good yields. Melting curves of duplexes containing 2-azahypoxanthine paired with the four natural bases at pH 6 and pH 8 proved that 2-azahypoxanthine base pairs were less stable than perfectly matched duplexes but showed little variation among different bases.
• US8742101B2
  申请人：——

  公开号：US8742101B2

  公开（公告）日：2014-06-03