propyl 1-S β-D-xylopyranoside | 26548-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propyl 1-S β-D-xylopyranoside
• 英文别名: propyl 1-thio-β-D-xylopyranoside；propyl-1-S-β-xylopyranoside；1-S-propyl-β-D-xylopyranoside；(2S,3R,4S,5R)-2-propylsulfanyloxane-3,4,5-triol
• CAS: 26548-25-4
• 化学式: C₈H₁₆O₄S
• 分子量: 208.279
• InChiKey: BFQAMGXXQARPNW-CWKFCGSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  95.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-propylsulfanyl-tetrahydro-pyran-3-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 propyl 1-S β-D-xylopyranoside
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.

  DOI：

  10.1021/jm8008713

文献信息

• Pentose derivatives as anti-hyperglycemic drugs
  申请人：Sasson Shlomo

  公开号：US20050277599A1

  公开（公告）日：2005-12-15

  The present invention relates to pentose and pentose derivatives that are effective at increasing glucose transport in a non-insulin dependent manner, and to uses thereof for a) treating and/or preventing hyperglycemia; b) treating and/or preventing the complications of hyperglycemia; c) treating diabetes; d) increasing the rate of cellular glucose transport; e) increasing the rate of cellular glucose uptake; f) improving the ability of a subject to metabolize glucose; g) treating daily blood glucose fluctuations; h) reducing blood sugar levels; i) reducing the dosage of anti-diabetic medication needed for treatment of diabetes. The present invention further provides novel pentose derivatives having beneficial properties in terms of pharmacokinetics, to pharmaceutical compositions comprising these novel compounds and uses thereof.

  本发明涉及以非胰岛素依赖方式有效增加葡萄糖转运的戊糖和戊糖衍生物，并涉及其用于 a) 治疗和/或预防高血糖；b) 治疗和/或预防高血糖并发症；c) 治疗糖尿病；d) 增加细胞葡萄糖转运率； e) 增加细胞葡萄糖摄取率； f) 改善受试者代谢葡萄糖的能力； g) 治疗日常血糖波动； h) 降低血糖水平； i) 减少治疗糖尿病所需的抗糖尿病药物剂量。本发明进一步提供了在药代动力学方面具有有益特性的新型戊糖衍生物，以及包含这些新型化合物的药物组合物及其用途。
• NOVEL PENTOSE DERIVATIVES AS ANTI-HYPERGLYCEMIC DRUGS
  申请人：Yissum Research Development Company of the Hebrew University of Jerusalem Ltd.

  公开号：EP1554299B1

  公开（公告）日：2013-01-30
• US7812142B2
  申请人：——

  公开号：US7812142B2

  公开（公告）日：2010-10-12
• [EN] NOVEL PENTOSE DERIVATIVES AS ANTI-HYPERGLYCEMIC DRUGS<br/>[FR] NOUVEAUX DERIVES DE PENTOSES UTILISES EN TANT DE MEDICAMENTS ANTI-HYPERGLYCEMIQUES
  申请人：YISSUM RES DEV CO

  公开号：WO2004034960A2

  公开（公告）日：2004-04-29

  The present invention relates to pentose and pentose derivatives that are effective at increasing glucose transport in a non-insulin dependent manner, and to uses thereof for a) treating and/or preventing hyperglycemia; b) treating and/or preventing the complications of hyperglycemia; c) treating diabetes; d) increasing the rate of cellular glucose transport; e) increasing the rate of cellular glucose uptake; f) improving the ability of a subject to metabolize glucose; g) treating daily blood glucose fluctuations; h) reducing blood sugar levels; i) reducing the dosage of anti-diabetic medication needed for treatment of diabetes. The present invention further provides novel pentose derivatives having beneficial properties in terms of pharmacokinetics, to pharmaceutical compositions comprising these novel compounds and uses thereof.
• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.