5'-O-(dimethoxytrityl)-2-azainosine | 171614-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5'-O-(dimethoxytrityl)-2-azainosine
• 英文别名: 5’-DMT-2-azainosine；7-[(2R,3R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3,4-dihydroxyoxolan-2-yl]-3H-imidazo[4,5-d]triazin-4-one
• CAS: 171614-02-1
• 化学式: C₃₀H₂₉N₅O₇
• 分子量: 571.59
• InChiKey: CTPVHNFFCNCIRI-CTDWIVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  149
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(dimethoxytrityl)-2-azainosine 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 19.0h， 生成 3'-O-(tert-butyldimethylsilyl)-5'-O-(dimethoxytrityl)-2'-(phenoxythiocarbonyl)-2-azainosine
  参考文献：
  名称：

  Synthesis and Biophysical and Biological Properties of Oligonucleotides Containing 2-Aza-2'-Deoxyinosine

  摘要：

  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.

  DOI：

  10.1021/jo00125a009
• 作为产物：
  描述：

  阿卡地新 在 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 2.58h， 生成 5'-O-(dimethoxytrityl)-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

• Discovery of BI 7446: A Potent Cyclic Dinucleotide STING Agonist with Broad-Spectrum Variant Activity for the Treatment of Cancer
  作者：Christian A. Kuttruff、Martin Fleck、Sebastian Carotta、Heribert Arnhof、Tom Bretschneider、Georg Dahmann、Gabriela Gremel、Achim Grube、Sandra Handschuh、Annekatrin Heimann、Marco H. Hofmann、Maria A. Impagnatiello、Herbert Nar、Georg Rast、Otmar Schaaf、Esther Schmidt、Thorsten Oost

  DOI：10.1021/acs.jmedchem.3c00510

  日期：2023.7.27
• CYCLIC DINUCLEOTIDE COMPOUNDS CONTAINING 2-AZA-HYPOXANTHINE OR 6H-PYTAZOLO[1,5-D][1,2,4]TRIZAIN-7-ONE AS STRING AGONISTS
  申请人：BOEHRINGER INGELHEIM INTERNATIONAL GMBH

  公开号：US20210009627A1

  公开（公告）日：2021-01-14

  Compounds of formula I, wherein Base, R 1 and R 2 are defined as in claim 1 , are modulators of STING.
• [EN] CYCLIC DINUCLEOTIDE COMPOUNDS CONTAINING 2-AZA-HYPOXANTHINE OR 6H-PYTAZOLO[1,5-D][1,2,4]TRIAZIN-7-ONE AS STING AGONISTS<br/>[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
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2019185477A1

  公开（公告）日：2019-10-03

  Compounds of formula I, wherein Base, R1 and R2 are defined as in claim 1, are modulators of STING.

  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。
• 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.