methyl-1-α-D-(2,3,4-tri-O-benzyl)-6-O-(9-[2-nitro-1H-imidazolyl]hydroxypropyl)glucopyranose | 1232866-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-1-α-D-(2,3,4-tri-O-benzyl)-6-O-(9-[2-nitro-1H-imidazolyl]hydroxypropyl)glucopyranose
• 英文别名: 1-(2-nitro-1H-imidazol-1-yl)-3-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)propan-2-ol；1-[[(2R,3R,4S,5R,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3-(2-nitroimidazol-1-yl)propan-2-ol
• CAS: 1232866-18-0
• 化学式: C₃₄H₃₉N₃O₉
• 分子量: 633.698
• InChiKey: AYBPFASSUSVYPP-SWNJJKEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl-1-α-D-(2,3,4-tri-O-benzyl)-6-O-(9-[2-nitro-1H-imidazolyl]hydroxypropyl)glucopyranose 在 二乙胺基三氟化硫 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到1-(2-fluoro-3-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)propyl)-2-nitro-1H-imidazole
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL IN DELIVERING ANTI-NEOPLASTIC THERAPY AND DIAGNOSTIC IMAGING TO HYPOXIC CELLS AND METHODS OF USE THEREOF
  [FR] COMPOSÉS UTILES DANS L'ADMINISTRATION D'UNE THÉRAPIE ANTINÉOPLASIQUE ET EN IMAGERIE DIAGNOSTIQUE DE CELLULES HYPOXIQUES ET PROCÉDÉS POUR LES UTILISER

  摘要：

  公开号：

  WO2010073126A3
• 作为产物：
  描述：

  2-硝基咪唑 、 1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose 在 caesium carbonate 作用下， 以 乙醇 为溶剂， 反应 27.0h， 以78%的产率得到methyl-1-α-D-(2,3,4-tri-O-benzyl)-6-O-(9-[2-nitro-1H-imidazolyl]hydroxypropyl)glucopyranose
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL IN DELIVERING ANTI-NEOPLASTIC THERAPY AND DIAGNOSTIC IMAGING TO HYPOXIC CELLS AND METHODS OF USE THEREOF
  [FR] COMPOSÉS UTILES DANS L'ADMINISTRATION D'UNE THÉRAPIE ANTINÉOPLASIQUE ET EN IMAGERIE DIAGNOSTIQUE DE CELLULES HYPOXIQUES ET PROCÉDÉS POUR LES UTILISER

  摘要：

  公开号：

  WO2010073126A3

文献信息

• Design, Synthesis, and Preliminary Biological Evaluation of 6-<i>O</i>-Glucose–Azomycin Adducts for Diagnosis and Therapy of Hypoxic Tumors
  作者：Piyush Kumar、Gennady Shustov、Hong Liang、Vladimir Khlebnikov、Weizhong Zheng、Xiao-Hong Yang、Chris Cheeseman、Leonard I. Wiebe

  DOI：10.1021/jm2017336

  日期：2012.7.12

  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.