3'-O-(4-methoxybenzyl)adenosine | 81366-75-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3'-O-(4-methoxybenzyl)adenosine
• 英文别名: (2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)tetrahydrofuran-3-ol；(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)-4-[(4-methoxyphenyl)methoxy]oxolan-3-ol
• CAS: 81366-75-8
• 化学式: C₁₈H₂₁N₅O₅
• 分子量: 387.395
• InChiKey: TUTLIZITRMOVIK-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3'-O-(4-methoxybenzyl)adenosine 在 吡啶 、 ammonium hydroxide 、 sodium azide 、 四溴化碳 、 四丁基碘化铵 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS
  [FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING

  摘要：

  揭示了一种通过调节STING来治疗受影响的疾病、综合征或紊乱的化合物、组合物和方法。这些化合物由以下式（I）表示：其中B2、X2、R2a、R2b、R2c、Z-M-Y、Y1-M1Z1、B1、X1、R1a、R1b、R1c如本文所定义。

  公开号：

  WO2019118839A1
• 作为产物：
  描述：

  4-甲氧基氯苄 、 腺苷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 21.5h， 以75 g的产率得到(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)tetrahydrofuran-3-ol
  参考文献：
  名称：

  [EN] CYCLIC DINUCLEOTIDES AS STING AGONISTS
  [FR] DINUCLÉOTIDES CYCLIQUES UTILISÉS EN TANT QU'AGONISTES DE STING

  摘要：

  揭示了一种通过调节STING来治疗受影响的疾病、综合征或紊乱的化合物、组合物和方法。这些化合物由以下式（I）表示：其中B2、X2、R2a、R2b、R2c、Z-M-Y、Y1-M1Z1、B1、X1、R1a、R1b、R1c如本文所定义。

  公开号：

  WO2019118839A1

文献信息

• [EN] COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1<br/>[FR] COMPOSITIONS ET PROCÉDÉS DE MODULATION DE LA RÉPONSE IMMUNITAIRE PAR ACTIVATION DE LA PROTÉINE KINASE ALPHA 1
  申请人：SHANGHAI YAO YUAN BIOTECHNOLOGY CO LTD

  公开号：WO2019080898A1

  公开（公告）日：2019-05-02

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are defined herein.

  该披露提供了与激活α-激酶1（ALPK1）相关的组合物和方法，用于调节免疫应答，治疗或预防癌症、感染、炎症和相关疾病和疾病，以及增强对靶抗原的免疫应答。该披露还提供了式（I）的杂环化合物作为α蛋白激酶1（ALPK1）的激动剂，并其在激活ALPK1、调节免疫应答和治疗癌症等疾病中的应用，其中A1、A2、L1、L2、L3、Z1、Z2、W1、W2、R1、R2、R3、R4、R5、R6和R7在此定义。
• SYNTHESIS OF OLIGORIBONUCLEOTIDES USING 4-METHOXYBENZYL GROUP AS A NEW PROTECTING GROUP OF THE 2′-HYDROXYL GROUP OF ADENOSINE
  作者：Hiroshi Takaku、Kazuo Kamaike

  DOI：10.1246/cl.1982.189

  日期：1982.2.5

  4-Methoxybenzyl group was introduced directly to the 2′-hydroxyl group from the reaction of adenosine with 4-methoxybenzyl bromide in the presence of sodium hydride. The 2′-O-(4-methoxybenzyl)adenosine can be successfully used in the synthesis of oligoribonucleotides via phosphotriester approach. The 4-methoxybenzyl group was removed rapidly from the oligoribonucleotides by triphenylmethyl fluoroborate

  4-甲氧基苄基在氢化钠存在下直接引入腺苷与4-甲氧基苄基溴反应的2'-羟基中。2'-O-(4-甲氧基苄基)腺苷可成功用于通过磷酸三酯法合成寡核糖核苷酸。4-甲氧基苄基通过氟硼酸三苯甲酯从寡核糖核苷酸中快速去除，并且完全解封闭的寡核糖核苷酸通过酶水解表征。
• Compositions and methods of modulating the immune response by activating alpha protein kinase 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US11149051B2

  公开（公告）日：2021-10-19

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A1, A2, L1, L2, L3, Z1, Z2, W1, W2, R1, R2, R3, R4, R5, R6 and R7 are defined herein.

  本公开提供了与激活α蛋白激酶1（ALPK1）有关的组合物和方法，用于调节免疫反应和治疗或预防癌症、感染、炎症及相关疾病和失调，以及增强对靶抗原的免疫反应。本公开还提供了作为α蛋白激酶1（ALPK1）激动剂的式(I)杂环化合物及其在激活ALPK1、调节免疫应答和治疗癌症等疾病中的用途，其中A1、A2、L1、L2、L3、Z1、Z2、W1、W2、R1、R2、R3、R4、R5、R6和R7在本文中定义。
• Investigation and Conformational Analysis of Fluorinated Nucleoside Antibiotics Targeting Siderophore Biosynthesis
  作者：Surendra Dawadi、Kishore Viswanathan、Helena I. Boshoff、Clifton E. Barry、Courtney C. Aldrich

  DOI：10.1021/acs.joc.5b00550

  日期：2015.5.15

  Antibiotic resistance represents one of the greatest threats to public health. The adenylation inhibitor 5'-O-[N-(salicyl)sulfamoyl]adenosine (SAL-AMS) is the archetype for a new class of nucleoside antibiotics that target iron acquisition in pathogenic microorganisms and is especially effective against Mycobacterium tuberculosis, the causative agent of tuberculosis. Strategic incorporation of fluorine at the 2' and 3' positions of the nucleoside was performed by direct fluorination to enhance activity and improve drug disposition properties. The resulting SAL-AMS analogues were comprehensively assessed for biochemical potency, whole-cell antitubercular activity, and in vivo pharmacokinetic parameters. Conformational analysis suggested a strong preference of fluorinated sugar rings for either a 2'-endo, 3'-exo (South), or a 3'-endo,2'-exo (North) conformation. The structureactivity relationships revealed a strong conformational bias for the C3'-endo conformation to maintain potent biochemical and whole-cell activity, whereas improved pharmacokinetic properties were associated with the C2'-endo conformation.
• COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1
  申请人：Shanghai Yao Yuan Biotechnology Co., Ltd.

  公开号：US20200283468A1

  公开（公告）日：2020-09-10

  The disclosure provides compositions and methods related to activating alpha-kinase 1 (ALPK1) for modulating an immune response and treating or preventing cancer, infection, inflammation and related diseases and disorders as well as potentiating an immune response to a target antigen. The disclosure also provides heterocyclic compounds of formula (I) as agonists of alpha protein kinase 1 (ALPK1) and their use in activating ALPK1, modulating an immune response and treating diseases such as cancer, wherein A 1 , A 2 , L 1 , L 2 , L 3 , Z 1 , Z 2 , W 1 , W 2 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined herein.