α-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate]

• 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: α-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate]
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis[[3,5-bis(phenylmethoxy)benzoyl]oxy]oxan-2-yl]methyl 3,5-bis(phenylmethoxy)benzoate
• 化学式: C₁₁₁H₉₂O₂₁
• 分子量: 1761.94
• InChiKey: DTCCMIRRGOXHQF-CLIVJKMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  132
• 可旋转键数：
  46
• 环数：
  16.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  233
• 氢给体数：
  0
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  α-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate] 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以83.7%的产率得到[(2R,3R,4S,5R,6R)-3,4,5,6-tetrakis[(3,5-dihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,5-dihydroxybenzoate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Antidiabetic Penta-O-galloyl-d-glucopyranose and Its Analogues

  摘要：

  The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the alpha- and beta-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-alpha-D-glucopyranose (43) and tetra-O-galloyl-alpha-D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy- 1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.

  DOI：

  10.1021/jm060087k
• 作为产物：
  描述：

  a-无水葡萄糖酯 、 3,5-二苄氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以39.3%的产率得到α-D-glucopyranose-1,2,3,4,6-pentakis[3,5-bis(phenylmethoxy)benzoate]
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationship Study of Antidiabetic Penta-O-galloyl-d-glucopyranose and Its Analogues

  摘要：

  The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the alpha- and beta-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-alpha-D-glucopyranose (43) and tetra-O-galloyl-alpha-D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy- 1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.

  DOI：

  10.1021/jm060087k

文献信息

• [EN] GP120 -BINDING BENZENE COMPOUNDS AND SACCHARIDE COMPOUNDS<br/>[FR] COMPOSÉS DE BENZÈNES ET DE SACCHARIDES SE LIANT À GP120
  申请人：UNIV LEUVEN KATH

  公开号：WO2011085454A1

  公开（公告）日：2011-07-21

  The present invention provides for novel benzene compounds and saccharide compounds and for the use of said compounds for binding, titration (quantification), removing, purifying or separating the glycoprotein gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention also provides for a method for the detection, binding, titration (quantification), removal, purification or separation of (or directing therapeutic or other agents to) gp120, gp120 comprising viruses or cells infected with gp120 comprising viruses. The invention further provides for the use of the compounds and for methods using the compounds for directing anti -viral drugs or other agents to gp120 comprising viruses or to gp120 comprising virus - infected cells. The present invention also provides processes for the preparation of said novel compounds.

  本发明提供了新型苯化合物和糖化合物，并用于结合、滴定（定量）、去除、纯化或分离含有糖蛋白gp120的化合物的用途，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明还提供了一种用于检测、结合、滴定（定量）、去除、纯化或分离（或将治疗或其他药物引导至）gp120的方法，该gp120包括病毒或感染有包含gp120病毒的细胞。本发明进一步提供了利用这些化合物的用途，以及用于将抗病毒药物或其他药物引导至含有gp120的病毒或含有gp120病毒感染细胞的方法。本发明还提供了用于制备这些新型化合物的工艺。
• Synthesis and Structure−Activity Relationship Study of Antidiabetic Penta-<i>O</i>-galloyl-<scp>d</scp>-glucopyranose and Its Analogues
  作者：Yulin Ren、Klaus Himmeldirk、Xiaozhuo Chen

  DOI：10.1021/jm060087k

  日期：2006.5.1

  The rapid increase of obesity-associated diabetes has created urgent demands for more effective antidiabetic therapies and pharmaceuticals that are able to address the problems of hyperglycemia and weight gain simultaneously. Our previous studies indicated that the alpha- and beta-anomers of penta-O-galloyl-D-glucopyranose (PGG), 2 and 3, act as insulin mimetics that bind to and activate the insulin receptor, stimulate glucose transport in adipocytes, and reduce blood glucose and insulin levels in diabetic and obese animals. In addition, they inhibit differentiation of preadipocytes into adipocytes. These activities suggest that 2 and 3 may reduce blood glucose without increasing adiposity. To investigate the structure-activity relationship of 2 and 3, four series of novel compounds were prepared and their glucose transport stimulatory activities were measured using a radioactive glucose uptake bioassay. The assay results indicate that both the glucose and the galloyl groups are critical to the activity of 2 and 3. It appears that the glucose core provides an optimal scaffold to present the galloyl groups with the correct spatial orientation to induce activity. Moreover, the galloyl groups linked to the 1, 2, 3, and 4 positions of glucose are essential, while the galloyl group connected to the 6 position of 2 is unnecessary for the induction of activity. The discovery that two related novel compounds, 6-deoxytetra-O-galloyl-alpha-D-glucopyranose (43) and tetra-O-galloyl-alpha-D-xylopyranose (59), also possess glucose transport stimulatory activity suggests that 2 may be further modified around position 6 to modulate and enhance its efficacy. To test this hypothesis, we developed a new synthetic method that allows for the stereoselective preparation of derivatives of 2 that are modified on C-6. We found that 6-chloro-6-deoxy- 1,2,3,4-tetra-O-galloyl-alpha-D-glucopyranose (80) exhibits a significantly higher glucose transport stimulatory activity than 2. Its activity is comparable to that of insulin.