2',6'-dihydroxy-4-methoxydihydrochalcone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2',6'-dihydroxy-4-methoxydihydrochalcone
• 英文别名: 2',6'-Dihydroxy-4'-methoxydihydrochalcon；1-(2,6-Dihydroxyphenyl)-3-(4-methoxyphenyl)propan-1-one
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: JKGBZWLZBRANMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',6'-dihydroxy-4-methoxydihydrochalcone 、 甲基磺酰氯 在 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-Hydroxy-3-[(4-methoxyphenyl)methyl]chromen-4-one
  参考文献：
  名称：

  New homoisoflavonoid analogues protect cells by regulating autophagy

  摘要：

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.086
• 作为产物：
  描述：

  2',6'-二(苄氧基)苯乙酮 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 2',6'-dihydroxy-4-methoxydihydrochalcone
  参考文献：
  名称：

  Na（+）-葡萄糖共转运蛋白抑制剂作为抗糖尿病药。I.基于新概念的4′-脱羟基phrizrizin衍生物的合成和药理性质。

  摘要：

  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

  DOI：

  10.1248/cpb.44.1174

文献信息

• 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。
• US5424406A
  申请人：——

  公开号：US5424406A

  公开（公告）日：1995-06-13
• US5731292A
  申请人：——

  公开号：US5731292A

  公开（公告）日：1998-03-24
• New homoisoflavonoid analogues protect cells by regulating autophagy
  作者：Li-She Gan、Lin-Wei Zeng、Xiang-Rong Li、Chang-Xin Zhou、Jie Li

  DOI：10.1016/j.bmcl.2017.01.086

  日期：2017.3

  As a special group of naturally occurring flavonoids, homoisoflavonoids have been discovered as active components of several traditional Chinese medicines for nourishing heart and mind. In this study, twenty homoisoflavonoid analogues, including different substitution groups on rings A and B, as well as heteroaromatic B ring, were synthesized and evaluated for their cardioprotective and neuroprotective activities. In a H2O2-induced H9c2 cardiomyocytes injury assay, nine homoisoflavonoid analogues showed promising activities in the same level as the positive control, diazoxide. Six cardioprotective compounds with representative structure diversities were then evaluated for their neuroprotective effects on MPP+ induced SH-SY5Y cell injury model. Furthermore, autophagy inducing monodansylcadaverine (MDC) fluorescence staining methods and molecular docking studies indicated the action mechanism of these compounds may involve autophagy regulating via class I P13K signaling pathway. (C) 2017 Elsevier Ltd. All rights reserved.
• 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