4-methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine | 16754-81-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
• 英文别名: 4-methoxy-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine；4-methoxy-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine；4-Methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-b>pyrimidin；1-(4-methoxy-pyrrolo[2,3-b]pyrimidin-7-yl)-β-D-1-deoxy-ribofuranose；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-methoxypyrrolo[2,3-d]pyrimidin-7-yl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(4-methoxypyrrolo[2,3-d]pyrimidin-7-yl)oxolane-3,4-diol
• CAS: 16754-81-7
• 化学式: C₁₂H₁₅N₃O₅
• 分子量: 281.268
• InChiKey: YSHDAMLQPKTCBM-MFYTUXHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到7-去氮杂肌苷
  参考文献：
  名称：

  Structural Determinants for N1/N7 Cyclization of Nicotinamide Hypoxanthine 5‘-Dinucleotide (NHD⁺) Derivatives by ADP-Ribosyl Cyclase from Aplysia californica:  Ca²⁺-Mobilizing Activity of 8-Substituted Cyclic Inosine 5‘-Diphosphoribose Analogues in T-Lymphocytes

  摘要：

  A series of nicotinamide hypoxanthine 5'-dinucleotide (NHD+) analogues modified at C-8 (2-5) and 7-deaza-NHD+ were synthesized, and cyclization in the presence of Aplysia ADP-ribosyl cyclase was studied. All 8-substituted NHD+ analogues were converted into their N1-cyclic forms by the enzyme, while in contrast, 7-deaza- NHD+ 17 was hydrolyzed into 7-deazainosine 5'-diphosphoribose (7-deaza- IDPR) 25. Correlations are made showing that the conformation of the NHD+ substrate is the key to successful cyclization. The pharmacological activities of these novel cIDPR derivatives were evaluated in both permeabilized and intact Jurkat T-lymphocytes. The results show that in permeabilized cells both 8-iodo 1g and 8-N3-N1-cIDPR 1d have an activity comparable to that of cADPR, while 8-iodo 1g and 8-phenyl-N1-cIDPR 1c have a small but significant effect in intact cells and can therefore be regarded as membrane-permeant; thus, cIDPR derivatives are emerging as important novel biological tools to study cADPR-mediated Ca2+ release in T-cells.

  DOI：

  10.1021/jm060275a
• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-((苯甲酰氧基)甲基)-5-(4-氯-5-碘-7H-吡咯并[2 在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.5h， 生成 4-methoxy-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides

  摘要：

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.

  DOI：

  10.1021/jm4018948

文献信息

• NOVEL SUBSTITUTED 7-DEAZAPURINE RIBONUCLEOSIDES FOR THERAPEUTIC USES
  申请人：Institute of Organic Chemistry and Biochemistry ASCR, v.v.i.

  公开号：US20160159844A1

  公开（公告）日：2016-06-09

  Compounds of Formula I and a pharmaceutically acceptable salt thereof, an optical isomer thereof, or a mixture of optical isomers thereof, as well as compositions which include such compounds and therapeutic methods that utilize such compounds and/or compositions.

  化合物I的盐，其药用上可以接受的盐，其光学异构体或其光学异构体的混合物，以及包括这些化合物的组合物和利用这些化合物和/或组合物的治疗方法。
• Miles, Robert W.; Samano, Vicente; Robins, Morris J., Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5951 - 5957
  作者：Miles, Robert W.、Samano, Vicente、Robins, Morris J.

  DOI：——

  日期：——
• US9586986B2
  申请人：——

  公开号：US9586986B2

  公开（公告）日：2017-03-07