1,5-anhydro-2-(adenin-9-yl)-2-deoxy-D-altrohexitol | 168695-97-4

• 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: 1,5-anhydro-2-(adenin-9-yl)-2-deoxy-D-altrohexitol
• 英文别名: 1,5-anhydro-2-deoxy-2-(adenin-9-yl)-D-altro-hexitol；2-(adenin-9-yl)-1,5-anhydro-2-deoxy-D-altro-hexitol；(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 168695-97-4
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: PWZYNABVNQRQCF-MTSNSDSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2-(adenin-9-yl)-2-deoxy-D-altrohexitol 、 4-甲氧基三苯基氯甲烷 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Aminoacyl-tRNA Synthetase Inhibitors as Potent and Synergistic Immunosuppressants

  摘要：

  The aminoacyl-tRNA synthetase family of enzymes is the target of many antibacterials and inhibitors of eukaryotic hyperproliferation. In screening analogues of 5'-O-(N-L-aminoacyl)-sulfamoyladenosine containing all 20 proteinogenic amino acids, we found these compounds to have potent immunosuppressive activity. Also, we found that combinations of these compounds inhibited the immune response synergistically. Based on these data, analogues with modifications at the aminoacyl and ribose moieties were designed and evaluated, and several of these showed high immunosuppressive potency, with one compound having an IC(50) of 80 nM, when tested in a cellular mixed lymphocyte reaction assay. Apart from showing the potential of aminoacyl-tRNA synthetase inhibitors as immunosuppressants, the current study also provides arguments for careful evaluation of the immunosuppressive activity of developmental antibacterials that target these enzymes.

  DOI：

  10.1021/jm8000746
• 作为产物：
  描述：

  2-(6-氨基-9H-嘌呤-9-基)-1,5-脱水-2-脱氧-4,6-O-[(R)-苯基亚甲基]-D-阿卓糖醇 在 溶剂黄146 作用下， 反应 2.0h， 以61%的产率得到1,5-anhydro-2-(adenin-9-yl)-2-deoxy-D-altrohexitol
  参考文献：
  名称：

  受保护的D-麦芽糖醇核苷的合成作为寡核苷酸合成的基础

  摘要：

  与腺嘌呤和尿嘧啶碱基部分d-阿卓糖醇核苷由1,5-环氧化物环的亲核开得到：2,3-二脱水-4,6- ø -亚苄基- d-蒜糖醇使用上述提到的钠盐基地。将2-三甲基甲硅烷基乙基保护基用于鸟嘌呤碱基的O 6-官能团在鸟嘌呤碱基的稳定性和N 9-位置可接受的烷基化产率之间提供了有用的折衷方案。从尿嘧啶同源物开始合成胞嘧啶核苷。3'-羟基官能团被苯甲酰基保护。

  DOI：

  10.1016/s0040-4020(99)00287-2

文献信息

• Synthesis of 1,5-Anhydro-2-(N6-Cyclopentyladenin-9-Yl)-2-Deoxy-D-Altrohexitol
  作者：I. Verheggen、A. Van Aerschot、N. Pillet、E. M. van der Wenden、A. Ijzerman、P. Herdewijn

  DOI：10.1080/15257779508012372

  日期：1995.5.1

  The N-6-cyclopentyladenosine (CPA) analogue (4) was synthesized in 10 steps starting from glucose. The results of the radioligand binding assays are consistent with the thus far published findings that compounds containing a six-membered moiety at N-9 exhibit extremely weak affinity for adenosine receptors. Replacement of the ribofuranosyl moiety of CPA (2) by a 2-deoxy-D-altohexitol moiety is sufficient to completely abolish its agonist activity.