adenosine 5'-phenylphosphonate | 40829-46-7

• 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: adenosine 5'-phenylphosphonate
• 英文别名: Adenosin-5'-phenylphosphonat；O^5'-(hydroxy-phenyl-phosphinoyl)-adenosine；phenyl-phosphonic acid adenosin-5'-yl ester；O^5'-(Hydroxy-phenyl-phosphinoyl)-adenosin；[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-phenylphosphinic acid
• CAS: 40829-46-7
• 化学式: C₁₆H₁₈N₅O₆P
• 分子量: 407.323
• InChiKey: LHRLVCSQQJKSEL-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  166
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  adenosine 3',5'-bisphenylphosphonate 在 acetate buffer 、 nuclease S₁ 、 水 作用下， 反应 0.17h， 生成 adenosine 5'-phenylphosphonate
  参考文献：
  名称：

  Substrate Properties of Adenosine- and Uridine- 3′, 5′-bisphenylphosphonates for 3′-Nucleotidase/Nucleases

  摘要：

  3', 5'-Bisphenylphosphonate and 5'-phenylphosphonate esters of adenosine and uridine were synthesized to investigate the substrate properties of the 3', 5'-bisphenylphosphonates for 3'-nucleotidase/nucleases. The V-max/apparent K-m values of the enzymes for them were found to be 9 to 21-fold higher than those for the corresponding nucleoside 3'-phenylphosphonates.

  DOI：

  10.1080/07328319608002456

文献信息

• Oligonucleotide compounds, their production and use
  申请人：TAKEDA CHEMICAL INDUSTRIES, LTD.

  公开号：EP0653438A2

  公开（公告）日：1995-05-17

  An oligonucleotide compound or a salt thereof, which has a nucleotide sequence represented by formula (I): wherein W represents hydrogen or a protective group; B1, B2 and B3 each represent nucleic acid residues, wherein each B2 may be the same or different when n is 2 or more; X1, X2 and X3 each represent OH, SH, C1-5 alkyl, C1 -5 alkoxy, C1 -5 monoalkylamino or an aromatic ring group which may be substituted or unsubstituted, wherein each X3 may be the same or different when n is 2 or more; R1, R2 and R3 each represent hydrogen, OH, halogen, C1 -5 alkoxy or C1 -5 alkoxyalkyloxy, wherein each R2 may be the same or different when n is 2 or more; and n represents an integer from 1 to 98 is disclosed. The oligonucleotides (I) of the present invention or the salts thereof can (1) inhibit expression of genes associated with the development of malignant tumors in malignant tumor cells, (2) inhibit expression of viral genes derived from viruses, (3) inhibit expression of genes producing proteins which contribute to the development of inflammations, (4) control expression of drug-resistant genes which cause complications in chemotherapy of malignant tumors, and (5) inhibit production of cell growth factors related to reangiostenosis after PCTA (percutaneous transluminal coronary angioplasty) by complementation to DNAs or mRNAs of genes inducing various diseases. They can be therefore used as antitumor agents, antiviral agents, antiinflammatory agents and drugs for controlling expression of specific genes such as resistance genes. These oligonucleotides can also be used as probes. Further, these oligonucleotides can be used in novel drug screening assays.

  一种寡核苷酸化合物或其盐，其核苷酸序列由式 (I) 表示： 其中 W 代表氢或保护基团；B1、B2 和 B3 各自代表核酸残基，其中当 n 为 2 或更多时，每个 B2 可相同或不同；X1、X2 和 X3 各自代表 OH、SH、C1-5 烷基、C1-5 烷氧基、C1-5 单烷基氨基或可被取代或未被取代的芳环基团，其中当 n 为 2 或更多时，每个 X3 可相同或不同；R1、R2 和 R3 各自代表氢、OH、卤素、C1 -5 烷氧基或 C1 -5 烷氧基，其中当 n 为 2 或更多时，每个 R2 可以相同或不同；n 代表 1 至 98 的整数。 本发明的寡核苷酸（I）或其盐类可以：(1) 抑制恶性肿瘤细胞中与恶性肿瘤发展有关的基因的表达；(2) 抑制来自病毒的病毒基因的表达；(3) 抑制产生有助于炎症发展的蛋白质的基因的表达、(4) 控制导致恶性肿瘤化疗并发症的耐药基因的表达，以及 (5) 通过与诱发各种疾病的基因的 DNA 或 mRNA 互补，抑制与经皮冠状动脉成形术（PCTA）后再狭窄有关的细胞生长因子的产生。因此，这些寡核苷酸可用作抗肿瘤药、抗病毒药、消炎药和控制特定基因（如抗性基因）表达的药物。这些寡核苷酸还可用作探针。此外，这些寡核苷酸还可用于新型药物筛选试验。
• 411. Nucleotides. Part VII. Analogues of adenosine-5? phosphate and uridine-5? phosphate containing phenylphosphonate and ethylphosphonate groups
  作者：Nity Anand、A. R. Todd

  DOI：10.1039/jr9510001867

  日期：——