2'-Deoxy-adenosine-5'-RP-monomethylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2'-Deoxy-adenosine-5'-RP-monomethylphosphonate
• 英文别名: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-methylphosphinic acid
• 化学式: C₁₁H₁₆N₅O₅P
• 分子量: 329.252
• InChiKey: YNCYIAAXFUCITC-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-O-乙酰基-2-脱氧腺苷酸 在 吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 反应 10.0h， 生成 2'-Deoxy-adenosine-5'-RP-monomethylphosphonate
  参考文献：
  名称：

  5′-Phosphonates of Ribonucleosides and 2′-Deoxyribonucleosides: Synthesis and Antiviral Activity

  摘要：

  5'-Phosphonates of natural 2'-deoxynucleosides and ribonucleosides were synthesized by condensation of 3'-O-acylated 2'-deoxynucleosides or 2',3'-substituted (2',3'-O-isopropylidene, 2',3'-O-methoxymethylene or 2',3'-O-ethoxymethylene) ribonucleosides. As condensing agents, either N,N'-dicyclohexylcarbodiimide or 2,4,6-triisopropylbenzenesulphonyl chloride were used. Nucleoside 5'-ethoxycarbonylphosphonates were converted into corresponding nucleoside 5'-aminocarbonylphosphonates by action of ammonia in methanol or aqueous ammonia. 5'-Hydrogenphosphonothioates of thymidine and 3'-deoxythymidine were obtained by reaction of phosphinic acid in the presence of pivaloyl chloride with 3'-O-acetylthymidine or 3'-deoxythymidine, respectively, followed by addition of powedered sulfur. 5'-O-methylenephosphonates of thymidine and 2'-deoxyadenosine were prepared by intramolecular reaction of corresponding 3'-O-iodomethylphosphonates under basic conditions. All compounds were tested for inhibition of several viruses, including HSV-2 and CMV, but showed no activity. A few compounds insignificantly inhibited HIV-1 reproduction. Thymidine 5'-hydrogenphosphonate neutralized anti-HIV action of 3'-azido-3'-deoxythymidine (AZT) and it indirectly showed that even some nucleoside 5'-phosphonates could be partly hydrolyzed in cell culture to corresponding nucleosides.

  DOI：

  10.1080/07328319308018558

文献信息

• OLIGONUCLEOTIDES MODIFIED TO IMPROVE STABILITY AT ACID pH
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：EP0690716A1

  公开（公告）日：1996-01-10
• EP0690716A4
  申请人：——

  公开号：EP0690716A4

  公开（公告）日：1997-05-02
• Antisense Oligonucleotides (ODN) Against SMAD7 and Uses Thereof in Medical Field
  申请人：Nogra Pharma Limited

  公开号：US20160304876A1

  公开（公告）日：2016-10-20

  The invention relates to antisense oligonucleotidic sequences (ODN) against Smad7 suitably modified, and their uses in medical field as therapeutic biological agents, in particular in the treatment of chronic inflammatory bowel disease, such as Crohn's disease and ulcerative colitis.
• FLAVOR COMPOSITIONS AND PET FOOD PRODUCTS CONTAINING THE SAME
  申请人：MARS, INCORPORATED

  公开号：US20180168208A1

  公开（公告）日：2018-06-21

  A flavor composition comprising at least one nucleotide derivative and/or at least one transmembrane compound that modulates, increases and/or enhances the activity of an umami receptor is provided that can be used to enhance the umami taste and/or palatability of food products. In certain, non-limiting embodiments, the flavor composition comprises at least one nucleotide derivative and/or at least one transmembrane compound, optionally at least one nucleotide, optionally at least one first amino acid, optionally at least one second amino acid.
• TLR MODULATORS AND METHODS OF USE
  申请人：CELGENE CORPORATION

  公开号：US20180289692A1

  公开（公告）日：2018-10-11

  Described herein are combinations comprising a SMAD7 oligonucleotide and a Toll-like receptor (TLR) modulator. Methods for using such combinations to treat disease conditions, including inflammatory disorders, such as inflammatory bowel disease (IBD), are also provided herein.