1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-phenylpropan-1-one | 1266170-07-3

• 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: 1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-phenylpropan-1-one
• 英文别名: 3-phenyl-1-[2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]propan-1-one
• CAS: 1266170-07-3
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: XQDFEYKTGPKVCI-VJXVFPJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  3-phenyl-1-(2,4,6-tris(benzyloxy)-3-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)prop-2-en-1-one 在 10% palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 生成 1-[3-(β-D-glucopyranosyl)-2,4,6-trihydroxyphenyl]-3-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis and antihyperglycemic activity of phenolic C-glycosides

  摘要：

  Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)(3) in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.031

文献信息

• Targeting Type 2 Diabetes with <i>C</i>-Glucosyl Dihydrochalcones as Selective Sodium Glucose Co-Transporter 2 (SGLT2) Inhibitors: Synthesis and Biological Evaluation
  作者：Ana R. Jesus、Diogo Vila-Viçosa、Miguel Machuqueiro、Ana P. Marques、Timothy M. Dore、Amélia P. Rauter

  DOI：10.1021/acs.jmedchem.6b01134

  日期：2017.1.26

  Inhibiting glucose reabsorption by sodium glucose co-transporter proteins (SGLTs) in the kidneys is a relatively new strategy for treating type 2 diabetes. Selective inhibition of SGLT2 over SGLT1 is critical for minimizing adverse side effects associated with SGLT1 inhibition. A library of C-glucosyl dihydrochalcones and their dihydrochalcone and chalcone precursors was synthesized and tested as SGLT1/SGLT2

  通过钠葡萄糖共转运蛋白（SGLT）抑制肾脏中的葡萄糖重吸收是治疗2型糖尿病的一种相对较新的策略。相对于SGLT1而言，对SGLT2的选择性抑制对于最小化与SGLT1抑制相关的不利副作用至关重要。合成了C-葡萄糖基二氢查耳酮及其二氢查耳酮和查耳酮前体的文库，并使用基于细胞的葡萄糖吸收荧光测定法测试了它们作为SGLT1 / SGLT2抑制剂的能力。SGLT2的最有效抑制剂（IC 50 = 9–23 nM）是SGLT1的较弱抑制剂（IC 50）= 10–19μM）。他们对葡萄糖转运蛋白的钠依赖性GLUT家族没有影响，最有效的对培养细胞没有急性毒性。通过计算对C-葡萄糖基二氢查耳酮与POPC膜的相互作用进行了建模，从而提供了它不是泛测定干扰化合物的证据。这些结果指向发现是有效且高度选择性的SGLT2抑制剂的结构。
• Synthesis and antihyperglycemic activity of phenolic C-glycosides
  作者：Preeti Rawat、Manmeet Kumar、Neha Rahuja、Daya Shankar Lal Srivastava、Arvind Kumar Srivastava、Rakesh Maurya

  DOI：10.1016/j.bmcl.2010.11.031

  日期：2011.1

  Various phenolic C-glycosides were evaluated for their in vitro and in vivo antihyperglycemic activity employing glucose uptake by rat muscle cell lines (L-6) and low dosed-streptozotocin-induced diabetic rats, respectively. Some of phenolic C-glycosides were isolated from Pterocarpus marsupium and Ulmus wallichiana and other were synthesized by unprotected sugar and phloroacetophenone using Sc(OTf)(3) in aqueous ethanol. Eight among tested compounds showed significant lowering of blood glucose level on low dosed-streptozotocin-induced diabetic rats. The compound 24 lowered the blood glucose levels by 34.9% and 33.6% during 0-5 h and 0-24 h, respectively, at the dose of 25 mg/kg body weight which is comparable to standard antidiabetic drug metformin. (C) 2010 Elsevier Ltd. All rights reserved.