methyl 5-deoxy-2,3-O-isopropylidene-D-erythropent-4-enofuranoside | 6991-65-7

• 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-O-isopropylidene-D-erythropent-4-enofuranoside
• 英文别名: (3aS,6aR)-6-methoxy-2,2-dimethyl-4-methylidene-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
• CAS: 6991-65-7
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: VPJWQGUSNANKFC-GCJDJSOWSA-N

物化性质

• 沸点：
  241.6±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-2,3-O-isopropylidene-D-erythropent-4-enofuranoside 在 palladium on activated charcoal 硫酸 、 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~85.0 ℃ 、344.74 kPa 条件下， 反应 16.0h， 生成 5-deoxy-2,3-O-isopropylidene-D-ribofuranose
  参考文献：
  名称：

  Adenosine Kinase Inhibitors. 3. Synthesis, SAR, and Antiinflammatory Activity of a Series of l-Lyxofuranosyl Nucleosides

  摘要：

  Chronic inflammatory diseases, such as arthritis and rheumatoid arthritis, remain major health problems worldwide. We previously demonstrated that adenosine kinase inhibitors (AKIs) exhibit antiinflammatory effects by inhibiting TNF-alpha production, neutrophil accumulation, and edema formation. Although adenosine receptor agonists produce similar effects, AKIs showed the antiinflammatory activity without the cardiovascular side effects that prevented the development of adenosine receptor specific agonists. However, previously described potent AKIs, such as 5-iodotubercidin, are nucleosides which have the potential to undergo in vivo 5'-O-phosphorylation and therefore produce cytotoxicity. In an effort to eliminate toxicities produced by phosphorylated nucleosides, L-lyxofuranosyl analogues of tubercidin were tested as potential AKIs since the opposite stereochemical. orientation of the CH2OH was expected to eliminate intracellular phosphorylation. Described herein are the discovery of a new series of AKIs based on alpha-L-lyxofuranosyl. nucleosides, their SAR, as well as the antiinflammatory activity of the lead compound GP790 (IC50 = 0.47 nM, 47% inhibition of paw swelling at 10 mg/kg in rat carrageenan paw edema model). In addition, a study showing that in the skin lesion model the antiinflammatory activity is reversed by an A2 selective adenosine receptor antagonist 3,7-dimethyl-1-propylxanthine (DMPX) is also described.

  DOI：

  10.1021/jm030230z

文献信息

• Inhibitors of E1 activating enzymes
  申请人：Langston P. Steven

  公开号：US20070191293A1

  公开（公告）日：2007-08-16

  This invention relates to compounds that inhibit E 1 activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

  该发明涉及抑制E1激活酶的化合物，包括这些化合物的药物组合物，以及使用这些化合物的方法。这些化合物可用于治疗疾病，特别是细胞增殖性疾病，包括癌症、炎症和神经退行性疾病；以及与感染和消瘦相关的炎症。
• INHIBITORS OF E1 ACTIVATING ENZYMES
  申请人：Langston Steven P.

  公开号：US20120258927A1

  公开（公告）日：2012-10-11

  This invention relates to compounds that inhibit E1 activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

  本发明涉及抑制E1激活酶的化合物，包括该化合物的制药组合物和使用该化合物的方法。该化合物可用于治疗疾病，特别是细胞增殖性疾病，包括癌症、炎症和神经退行性疾病；以及与感染和消瘦相关的炎症。
• INHIBITORS OF E1 ACTIVTING ENZYMES
  申请人：MILLENNIUM PHARMACEUTICALS, INC

  公开号：US20130289037A1

  公开（公告）日：2013-10-31

  This invention relates to compounds that inhibit E1 activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.

  本发明涉及抑制E1激活酶的化合物、包含该化合物的药物组合物以及使用该化合物的方法。该化合物对于治疗疾病特别是细胞增殖性疾病，包括癌症、炎症和神经退行性疾病；以及与感染和消瘦相关的炎症非常有用。
• Inhibitors of E1 Activating Enzymes
  申请人：Millennium Pharmaceuticals, Inc.

  公开号：EP2402334B1

  公开（公告）日：2016-06-29
• US8207177B2
  申请人：——

  公开号：US8207177B2

  公开（公告）日：2012-06-26