1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose | 189240-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose
• 英文别名: methyl 2,3,4-tri-O-benzyl-6-O-(2',3'-epoxypropyl)-α-D-glucopyranoside；(2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-methoxy-6-((oxiran-2-ylmethoxy)methyl)tetrahydro-2H-pyran
• CAS: 189240-75-3
• 化学式: C₃₁H₃₆O₇
• 分子量: 520.623
• InChiKey: PWFBBACGMBAFRO-YIFLBWMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.91
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose 在 sodium azide 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以93%的产率得到1-azido-3-(((2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methoxy)propan-2-ol
  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：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 环氧溴丙烷 在 calcium sulfate 、 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以89%的产率得到1-α-D-O-methyl-2,3,4-tri-O-benzyl-6-O-((-oxiran-2-yl)methyl)glucopyranose
  参考文献：
  名称：

  Syntheses of Methyl 2-O-, 3-O- and 6-O-(2′-Hydroxypropyl)-α-D-Glucopyranosides¹

  摘要：

  Methyl 6-O-, 3-O- and 2-O-(2'-hydroxypropyl)-alpha-D-glucopyranosides (4, 8, and 12) were synthesized starting from methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranoside (1), methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (5), and methyl 3-O-benzyl-4,6-O-benzylidene-D-glucopyranoside (9), respectively. Overall yields were 88%, 6% and 26% of 4, 8 and 12, respectively, with the 2-ether (12) being crystalline and the 3-ether (8) a single diastereomer.

  DOI：

  10.1080/07328309708006517

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.