2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside | 23141-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside
• 英文别名: 2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside)；2'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6'-hydroxyacetophenone；2'-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-6'-hydroxyacetophenone；[(2R,3R,4S,5R,6S)-6-(2-acetyl-3-hydroxyphenoxy)-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 23141-00-6
• 化学式: C₂₂H₂₆O₁₂
• 分子量: 482.441
• InChiKey: OYPBQTZFOSZANO-MIUGBVLSSA-N

物化性质

• 熔点：
  201–203°C
• 沸点：
  567.4±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  161
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 16.0h， 生成 1-[2-Hydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-3-quinolin-6-yl-propan-1-one
  参考文献：
  名称：

  Na+-Glucose Cotransporter Inhibitors as Antidiabetic Agents. II. Synthesis and Structure-Activity Relationships of 4'-Dehydroxyphlorizin Derivatives.

  摘要：

  合成了一系列4'-去羟基荭草苷衍生物，并评估了这些化合物对大鼠尿糖排泄的影响。活性对结构有严格的要求。在A环的3位和/或4位引入小取代基或平面环是允许的，但A环与B环之间的桥接部分或糖部分的任何改变会导致活性的完全丧失。B环上的6'-OH基团也是必要的，即使是6'-OH基团的小结构修改也会显著降低活性。在合成的化合物中，5-苯并呋喃衍生物25是最有效的，并被选为进一步结构-活性关系研究的新先导。

  DOI：

  10.1248/cpb.46.22
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 苄基三丁基氯化铵 、 potassium carbonate 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以93%的产率得到2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Solid-Liquid Phase Transfer Catalyzed Novel Glycosylation Reaction of Phenols

  摘要：

  A facile and mild glycosylation reaction in solid-liquid two-phase system (powdered K2CO3 / CHCl3) containing phase transfer catalyst was found to be efficient for preparation of glucosides of 2', 6' -dihydroxyacetophenone (1) and other various substituted phenols.

  DOI：

  10.1080/00397919908086444

文献信息

• Na+-Glucose Cotransporter Inhibitors as Antidiabetics. I. Synthesis and Pharmacological Properties of 4'-Dehydroxyphlorizin Derivatives Based on a New Concept.
  作者：Kenji TSUJIHARA、Mitsuya HONGU、Kunio SAITO、Masanori INAMASU、Kenji ARAKAWA、Akira OKU、Mamoru MATSUMOTO

  DOI：10.1248/cpb.44.1174

  日期：——

  Based on our new concept that inhibitors of the Na(+)-glucose cotransporter (SGLT) would be useful as antidiabetics, 4'-dehydroxyphlorizin derivatives 1a--f were designed, synthesized, and examined for various pharmacological properties related to antidiabetic activity. In normal rats, 1a, e and phlorizin showed a strong SGLT-inhibitory effect and significantly increased urinary glucose on intraperitoneal

  根据我们的新概念，即Na（+）-葡萄糖共转运蛋白（SGLT）的抑制剂将用作抗糖尿病药，设计，合成了4'-脱羟基Phrizrizin衍生物1a-f，并检查了与抗糖尿病活性相关的各种药理特性。在正常大鼠中，腹膜内给药10 mg / kg时，1a，e和phlorizin表现出较强的SGLT抑制作用并显着增加尿葡萄糖，尽管只有1a导致口服100 mg / kg时会排泄大量尿葡萄糖。在正常大鼠的肠灌注过程中，化合物1a，e和phlorizin显着抑制了小肠中的葡萄糖摄取。口服给药时，化合物1a在小鼠的葡萄糖耐量试验中对血糖具有明显的降低作用，并且还降低了链脲佐菌素诱导的糖尿病大鼠的血糖。糖苷配基2a，1a，e和1a的e对人红细胞中促进葡萄糖转运蛋白1（GLUT-1）的抑制作用较弱，而促视紫红质素对GLUT-1的抑制作用较强。当以1 g / kg的剂量连续给药4周后，化合物1a对大鼠没有明显的肾脏损害
• Propiophenone derivative and a process for preparing the same
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05830873A1

  公开（公告）日：1998-11-03

  A propiophenone derivative of the formula \x9bI!: ##STR1## wherein X is O, S or methylene, OY is a protected or unprotected OH, Z is .beta.-D-glucopyranosyl or 4-O-(.alpha.-D-glucopyranosyl)-.beta.-D-glucopyranosyl or wherein one or more hydroxy groups of these groups may optionally be acylated, and the dotted line means the presence or absence of a double bond, or a pharmaceutically acceptable salt thereof. Said compounds have excellent hypoglycemic activity so that they are useful in the prophylaxis or treatment of diabetes.

  该化合物为一种丙酮苯酮衍生物，化学式为\x9bI!: ##STR1## 其中X为O、S或亚甲基，OY为保护或未保护的OH，Z为β-D-葡萄糖吡喃糖苷或4-O-(α-D-葡萄糖吡喃糖苷)-β-D-葡萄糖吡喃糖苷，其中这些基团中的一个或多个羟基可以选择性地酰化，虚线表示双键的存在或不存在，或其药学上可接受的盐。这些化合物具有出色的降糖活性，因此它们在糖尿病的预防或治疗中非常有用。
• Propiophenone derivative and processes for preparing the same
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05767094A1

  公开（公告）日：1998-06-16

  A propiophenone derivative the formula \x9bI!: ##STR1## wherein R' is a lower alkanoyl group and R" is a hydrogen atom, or R' is a hydrogen atom and R" is a lower alkoxycarbonyl group, or a pharmaceutically acceptable salt thereof. Said compounds have excellent hypoglycemic activity so that they are useful in the prophylaxis or treatment of diabetes.

  一种丙酮苯衍生物，其化学式为\x9bI!: ##STR1## 其中R'是较低的烷酰基团，R"是氢原子，或者R'是氢原子，R"是较低的烷氧羰基基团，或其药学上可接受的盐。该化合物具有极好的降血糖活性，因此它们在糖尿病的预防或治疗中非常有用。
• Fused heterocyclic derivative, medicinal composition containing the same, and medicinal use thereof
  申请人：Fushimi Nobuhiko

  公开号：US20060247179A1

  公开（公告）日：2006-11-02

  The present invention provides fused heterocyclic derivatives represented by the general formula: wherein R 1 represents H, halogen, OH, etc.; R 2 represents H, halogen or an alkyl group; R 3 and R 4 represent H, OH, halogen, etc.; Q represents alkylene, etc.; ring A represents aryl or heteroaryl; and G represents , or pharmaceutically acceptable salts thereof, or prodrugs thereof, which exhibit an excellent inhibitory activity in human SGLT and are useful as agents for the prevention or treatment of a disease associated with hyperglycemia such as diabetes, postprandial hyperglycemia, impaired glucose tolerance, diabetic complications or obesity, pharmaceutical compositions comprising the same, and pharmaceutical uses thereof.

  本发明提供了由通式表示的融合杂环衍生物：其中R1代表H、卤素、OH等；R2代表H、卤素或烷基；R3和R4代表H、OH、卤素等；Q代表烷基等；环A代表芳基或杂芳基；G代表，或其药学上可接受的盐，或其前药，它们在人类SGLT中表现出优异的抑制活性，并且可用作预防或治疗与高血糖有关的疾病，如糖尿病、餐后高血糖、糖耐量受损、糖尿病并发症或肥胖症的药剂，以及它们的药用组合物和药用用途。
• Hypoglycemic dihydrochalcone derivatives
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0598359A1

  公开（公告）日：1994-05-25

  A hypoglycemic agent which comprises as an active ingredient a dihydrochalcone derivative of the formula [I]: wherein Ar is an aryl group, R¹ is hydrogen atom or an acyl group, R² is hydrogen atom, an acyl group or α-D-glucopyranosyl group, or R¹ and R² may combine together to form a substituted methylene group, R³ and R⁴ are each hydrogen atom or an acyl group, and a group of the formula: OR⁵ is a protected or unprotected hydroxy group or a lower alkoxy group, or a pharmaceutically acceptable salt thereof.

  一种降血糖药剂，其活性成分包括式 [I] 的二氢查尔酮衍生物： 其中Ar为芳基，R¹为氢原子或酰基，R²为氢原子、酰基或α-D-吡喃葡萄糖基，或R¹和R²可结合在一起形成取代的亚甲基，R³和R⁴各自为氢原子或酰基，以及一个式中的基团：OR⁵ 是受保护或未受保护的羟基或低级烷氧基，或其药学上可接受的盐。