((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate | 120312-98-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: ((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
• 英文别名: [(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-3-fluoro-4-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 120312-98-3
• 化学式: C₁₀H₁₃FN₅O₆P
• 分子量: 349.215
• InChiKey: YARNDPZCUIYKLZ-GQTRHBFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate 在 吡啶 、 四氮唑 作用下， 以 水 、 叔丁醇 为溶剂， 反应 32.0h， 生成 (2S,3S,4S,5R,6R)-2-(((((((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)(hydroxy)phosphoryl)oxy)-6-((R)-1,2-diacetoxyethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1
  [FR] COMPOSITIONS ET PROCÉDÉS DE MODULATION DE LA RÉPONSE IMMUNITAIRE PAR ACTIVATION DE LA PROTÉINE KINASE ALPHA 1

  摘要：

  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。

  公开号：

  WO2019080898A1
• 作为产物：
  描述：

  N⁶-trityl-9-[3-deoxy-3-fluoro-2-O-(4-methoxybenzyl)-β-D-xylofuranosyl]adenine 在 4,5-二氰基咪唑 、 palladium on activated charcoal 、 氢气 、 palladium(II) hydroxide 作用下， 以 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 25.0 ℃ 、344.75 kPa 条件下， 反应 53.17h， 生成 ((2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-3-fluoro-4-hydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS OF MODULATING THE IMMUNE RESPONSE BY ACTIVATING ALPHA PROTEIN KINASE 1
  [FR] COMPOSITIONS ET PROCÉDÉS DE MODULATION DE LA RÉPONSE IMMUNITAIRE PAR ACTIVATION DE LA PROTÉINE KINASE ALPHA 1

  摘要：

  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。

  公开号：

  WO2019080898A1

文献信息

• 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。
• Aplysia californica mediated cyclisation of novel 3′-modified NAD + analogues: a role for hydrogen bonding in the recognition of cyclic adenosine 5′-diphosphate ribose
  作者：Christopher J.W Mort、Marie E Migaud、Antony Galione、Barry V.L Potter

  DOI：10.1016/j.bmc.2003.10.012

  日期：2004.1

  Cyclic ADP-ribose mobilizes intracellular Ca2+ in a variety of cells. To elucidate the nature of the interaction between the C3' substituent of cADP-ribose and the cADPR receptor, three analogues of NAD(+) modified in the adenosine ribase (xyloNAD(+) 3'F-xyloNAD(+) and 3'F-NAD(+) were chemically synthesised from D-xylose and adenine starting materials. 3'F-NAD(+) was readily converted to cyclic 3'F-ADP ribose by the action of the cyclase enzyme derived from the mollusc Aplysia californica. XyloNAD(+) and 3'F-xyloNAD(+) were cyclised only reluctantly and in poor yield to afford unstable cyclic products. Biological evaluation of cyclic 3'F-ADP ribose for calcium release in sea urchin egg homogenate gave an EC50 of 1.5 +/- 0.5 muM. This high value suggests that the ability of the C3' substituent to donate a hydrogen bond is crucial for agonism. (C) 2003 Elsevier Ltd. All rights reserved.
• 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.