methyl 5-deoxy-2,3-di-O-benzoyl-D-ribofuranoside | 151378-79-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-2,3-di-O-benzoyl-D-ribofuranoside
• 英文别名: [(2R,3R,4R)-4-benzoyloxy-5-methoxy-2-methyloxolan-3-yl] benzoate
• CAS: 151378-79-9
• 化学式: C₂₀H₂₀O₆
• 分子量: 356.375
• InChiKey: WLHOVGKSTWSMOM-WLEDDMDJSA-N

物化性质

• 沸点：
  471.5±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-2,3-di-O-benzoyl-D-ribofuranoside 在 甲醇 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 sodium methylate 、 N,O-双(三甲基硅烷基)三氟乙酰胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 4-甲苯硫酚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.25h， 生成 去氧氟尿苷
  参考文献：
  名称：

  一种尿嘧啶核苷衍生物及该衍生物制备去氧氟尿苷药物的方法

  摘要：

  本发明公开了一种如通式(I)所示的5‑脱氧‑D‑呋喃核糖1‑[2‑(1‑苯乙烯基)苯甲酸酯]衍生物以及该衍生物的制备方法，其中通式(I)的结构为以及以通式(I)为原料制备尿嘧啶核苷衍生物和抗肿瘤药物去氧氟尿苷的方法。本发明用作上述反应原料的5‑脱氧‑D‑呋喃核糖1‑[2‑(1‑苯乙烯基)苯甲酸酯]衍生物作为糖基给体可以在催化量的路易斯酸三氟甲磺酸三甲基硅酯和N‑碘代丁二酰亚胺的条件下进行活化，避免了传统的使用当量或过量的路易斯酸，反应体系温和，无其它副反应发生，反应高效，收率达到98％。

  公开号：

  CN111072734B
• 作为产物：
  描述：

  methyl 5-deoxy-5-chloro-2,3-di-O-benzoyl-D-ribofuranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以88%的产率得到methyl 5-deoxy-2,3-di-O-benzoyl-D-ribofuranoside
  参考文献：
  名称：

  New adenosine kinase inhibitors with oral antiinflammatory activity: synthesis and biological evaluation

  摘要：

  Several 5-iodotubercidin analogues in the pyrazolo[3,4-d]pyrimidine ring system were synthesized as potential inhibitors of adenosine kinase by a direct Lewis acid-catalyzed glycosylation procedure using both the preformed carbohydrate and the heterocyclic base as starting materials. The 5'-hydroxyl, -chloro, -azido, -deoxy, -amino, and -fluoro derivatives were prepared and evaluated in three systems for biological activity relative to adenosine, the true substrate, and 5-iodotubercidin, a known inhibitor. First, each compound was studied kinetically for inhibition of purified human placental adenosine kinase activity. The order of potency was: iodotubercidin > hydroxyl > amino greater-than-or-equal-to deoxy > fluoro> chloro >> azido. The K(i) values for the 5'-hydroxyl and 5'-amino compounds, the two most potent inhibitors, were 80 and 150 nM, respectively. The inhibition appeared to be essentially competitive in nature, although a noncompetitive component of significance for the more potent inhibitors cannot be ruled out. Second, a bioassay was conducted in which the toxicity of 6-methylmercaptopurine riboside toward human CEM lymphoblasts was reversed by varying concentrations of the compounds. The order of effectiveness of the compounds in this system, representing a functional inhibition of adenosine kinase in cultured cells, was about the same as that with the purified enzyme, except that the 5'-chloro and 5'-fluoro compounds were ineffective. Third, the 5'-hydroxyl derivative was evaluated in vivo in a rat pleurisy inflammation model and displayed biological activity at a dose of 30 mg/kg given orally. Finally, the in vitro toxicity of each compound was assessed in CEM lymphoblasts. Results indicated that the two most potent inhibitors in the pyrazolo[3,4-d]pyrimidine ring system, the 5'-hydroxyl (7) and the 5'-amino (20), were 15-fold and 75-fold, respectively, less growth inhibitory than 5-iodotubercidin.

  DOI：

  10.1021/jm00074a024

文献信息

• 一种胞嘧啶核苷衍生物及该衍生物制备卡培他滨药物的方法
  申请人：中国科学院昆明植物研究所

  公开号：CN111100172B

  公开（公告）日：2023-03-17

  本发明公开了一种如通式(I)所示的5‑脱氧‑D‑呋喃核糖1‑[2‑(1‑苯乙烯基)苯甲酸酯]衍生物以及该衍生物的制备方法，其中通式(I)的结构为
• [EN] A METHOD OF TREATING DISORDERS RELATED TO CYTOKINES IN MAMMALS<br/>[FR] PROCEDE DE TRAITEMENT D'AFFECTIONS ASSOCIEES AUX CYTOKINES CHEZ LES MAMMIFERES
  申请人：NOVO NORDISK A/S

  公开号：WO1997033590A1

  公开（公告）日：1997-09-18

  (EN) A method of treating disorders related to cytokines such as TNF$g(a) in mammals. The disorder is an autoimmune disorder, inflammation, arthritis, type I or type II diabetes, multiple sclerosis, stroke, osteoporosis, septic shock or menstrual complications.(FR) Procédé de traitement d'affections associées aux cytokines telles que le facteur de nécrose des tumeurs $g(a) (TNF$g(a)) chez les mammifères. Cette affection peut être une affection autoimmune, une inflammation, l'arthrite, le diabète de type I ou II, la sclérose en plaques, une attaque, l'ostéoporose, un choc septique ou des complications menstruelles.