N-benzoyl-2-(benzoylamino)-2’-deoxy-2’-fluoroadenosine

• 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: N-benzoyl-2-(benzoylamino)-2’-deoxy-2’-fluoroadenosine
• 英文别名: N-[2-benzamido-9-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• 化学式: C₂₄H₂₁FN₆O₅
• 分子量: 492.466
• InChiKey: ZVLIHUPZBMJBIF-RSZAZKGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2-(benzoylamino)-2’-deoxy-2’-fluoroadenosine 在 吡啶 、 咪唑 、 磷酸三甲酯 、 sodium tetrahydroborate 、 adenosine deaminase from bovine spleen type IX 、 盐酸羟胺 、 对甲苯磺酸一水合物 、 四丁基氟化铵 、 三羟甲基氨基甲烷盐酸盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N'-羰基二咪唑 、 甲胺 、 三氟乙酸 、 sodium hydroxide 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 氯仿 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 86.5h， 生成 [[(2R,3R,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-2-cyano-4-fluoro-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
  参考文献：
  名称：

  Discovery of β-d-2′-deoxy-2′-α-fluoro-4′-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases

  摘要：

  Novel 4'-substituted beta-D-2'-deoxy-2'-alpha-fluoro (2'd2'F) nucleoside inhibitors of respiratory syncytial virus (RSV) are reported. The introduction of 4'-substitution onto 2'd2'F nucleoside analogs resulted in compounds demonstrating potent cell based RSV inhibition, improved inhibition of the RSV polymerase by the nucleoside triphosphate metabolites, and enhanced selectivity over incorporation by mitochondrial RNA and DNA polymerases. Selectivity over the mitochondrial polymerases was found to be extremely sensitive to the specific 4'-substitution and not readily predictable. Combining the most potent and selective 4'-groups from N-nucleoside analogs onto a 2'd2'F C-nucleoside analog resulted in the identification of beta-D-2'-deoxy-2'-alpha-fluoro-4'-alpha-cyano-5-aza-7,9-dideaza adenosine as a promising nucleoside lead for RSV. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.073
• 作为产物：
  描述：

  2-氨基-2'-氟-2'-脱氧腺苷 在 ammonium hydroxide 作用下， 以 吡啶 、 水 为溶剂， 反应 0.83h， 生成 N-benzoyl-2-(benzoylamino)-2’-deoxy-2’-fluoroadenosine
  参考文献：
  名称：

  Discovery of β-d-2′-deoxy-2′-α-fluoro-4′-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases

  摘要：

  Novel 4'-substituted beta-D-2'-deoxy-2'-alpha-fluoro (2'd2'F) nucleoside inhibitors of respiratory syncytial virus (RSV) are reported. The introduction of 4'-substitution onto 2'd2'F nucleoside analogs resulted in compounds demonstrating potent cell based RSV inhibition, improved inhibition of the RSV polymerase by the nucleoside triphosphate metabolites, and enhanced selectivity over incorporation by mitochondrial RNA and DNA polymerases. Selectivity over the mitochondrial polymerases was found to be extremely sensitive to the specific 4'-substitution and not readily predictable. Combining the most potent and selective 4'-groups from N-nucleoside analogs onto a 2'd2'F C-nucleoside analog resulted in the identification of beta-D-2'-deoxy-2'-alpha-fluoro-4'-alpha-cyano-5-aza-7,9-dideaza adenosine as a promising nucleoside lead for RSV. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.04.073

文献信息

• WO2020016782A5
  申请人：——

  公开号：WO2020016782A5

  公开（公告）日：2022-07-14
• CYCLIC DINUCLEOTIDES AS STING AGONISTS
  申请人：JANSSEN BIOTECH, INC.

  公开号：US20210277046A1

  公开（公告）日：2021-09-09

  Disclosed are compounds, compositions and methods for treating of diseases, syndromes, or disorders that are affected by the modulation of STING. Such compounds are represented by Formula (I), wherein R 1 , R 1 ′, X 1 , B 1 , R 2 , R 2 ′, B 2 , X 2 , R 3 , Z-M-Y, and Y 1 -M 1 -Z 1 are as defined herein.
• US5750675A
  申请人：——

  公开号：US5750675A

  公开（公告）日：1998-05-12
• Discovery of β-d-2′-deoxy-2′-α-fluoro-4′-α-cyano-5-aza-7,9-dideaza adenosine as a potent nucleoside inhibitor of respiratory syncytial virus with excellent selectivity over mitochondrial RNA and DNA polymerases
  作者：Michael O. Clarke、Richard Mackman、Daniel Byun、Hon Hui、Ona Barauskas、Gabriel Birkus、Byoung-Kwon Chun、Edward Doerffler、Joy Feng、Kapil Karki、Gary Lee、Michel Perron、Dustin Siegel、Swami Swaminathan、William Lee

  DOI：10.1016/j.bmcl.2015.04.073

  日期：2015.6

  Novel 4'-substituted beta-D-2'-deoxy-2'-alpha-fluoro (2'd2'F) nucleoside inhibitors of respiratory syncytial virus (RSV) are reported. The introduction of 4'-substitution onto 2'd2'F nucleoside analogs resulted in compounds demonstrating potent cell based RSV inhibition, improved inhibition of the RSV polymerase by the nucleoside triphosphate metabolites, and enhanced selectivity over incorporation by mitochondrial RNA and DNA polymerases. Selectivity over the mitochondrial polymerases was found to be extremely sensitive to the specific 4'-substitution and not readily predictable. Combining the most potent and selective 4'-groups from N-nucleoside analogs onto a 2'd2'F C-nucleoside analog resulted in the identification of beta-D-2'-deoxy-2'-alpha-fluoro-4'-alpha-cyano-5-aza-7,9-dideaza adenosine as a promising nucleoside lead for RSV. (C) 2015 Elsevier Ltd. All rights reserved.