1-α-D-(1,2,3,4-tetra-O-acetyl)-6-O-(9-[2-nitro-1H-imidazolyl]-8R-O-(acetyl)propyl)glucopyranose | 1383736-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-α-D-(1,2,3,4-tetra-O-acetyl)-6-O-(9-[2-nitro-1H-imidazolyl]-8R-O-(acetyl)propyl)glucopyranose
• CAS: 1383736-87-5
• 化学式: C₂₂H₂₉N₃O₁₄
• 分子量: 559.484
• InChiKey: NFFUJHPVHDQLPL-HETMTNPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  39.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  210.92
• 氢给体数：
  0.0
• 氢受体数：
  16.0

反应信息

• 作为产物：
  描述：

  methyl-1-(2,3,4-tri-O-benzyl)-6-O-(9-[2-nitro-1H-imidazolyl]-8-O-(acetyl)propyl)glucopyranose 、 乙酸酐 在 三氟甲磺酸三甲基硅酯 作用下， 反应 18.0h， 生成 1-β-D-(1,2,3,4-tetra-O-acetyl)-6-O-(9-[2-nitro-1H-imidazolyl]-O-(acetyl)propyl)glucopyranose 、 1-α-D-(1,2,3,4-tetra-O-acetyl)-6-O-(9-[2-nitro-1H-imidazolyl]-8R-O-(acetyl)propyl)glucopyranose 、 1-α-D-(1,2,3,4-tetra-O-acetyl)-6-O-(9-[2-nitro-1H-imidazolyl]-8S-O-(acetyl)propyl)glucopyranose
  参考文献：
  名称：

  Design, Synthesis, and Preliminary Biological Evaluation of 6-O-Glucose–Azomycin Adducts for Diagnosis and Therapy of Hypoxic Tumors

  摘要：

  Several 2-nitroimidazole-based molecules (NIs) are used as clinical hypoxic tumor radiodiagnostics, but they are not effective as radiosensitizers/radiochemotherapeutics. These NIs permeate tumor cells nonselectively via diffusion, and in therapy, where high doses are required, their dose limiting toxicities preclude success. The synthesis and preliminary in vitro evaluations of three glucoazomycins, members of a novel class of C6-O-glucose-linked-azomycin conjugates that are putative substrates of glucose transport proteins (GLUTs) and possess hypoxia-selective radiosensitization features, are now reported. The hypoxia-dependent upregulation of several GLUTs provides a rational basis to develop these glucoazomycins because more selective uptake in hypoxic cells would decrease systemic toxicities at effective doses. Calculated partition coefficients (ClogP, -1.70 to -2.99) predict rapid in vivo clearance for low systemic toxicity. In vitro experimental data show that glucoazomycins are radiosensitizers and that they competitively inhibit glucose uptake.

  DOI：

  10.1021/jm2017336