9-hydroxymethyl-4-methyl-9-piperidin-4-ylmethyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione | 1201629-43-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 9-hydroxymethyl-4-methyl-9-piperidin-4-ylmethyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione
• 英文别名: 9-(hydroxymethyl)-4-methyl-9-(piperidin-1-ylmethyl)-8H-pyrano[2,3-f]chromene-2,10-dione
• CAS: 1201629-43-7
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: AZZAETOIWLMYBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  哌啶 、 聚合甲醛 、 8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 以 乙醇 为溶剂， 反应 4.0h， 以74%的产率得到9-hydroxymethyl-4-methyl-9-piperidin-4-ylmethyl-8,9-dihydro-pyrano[2,3-f]chromene-2,10-dione
  参考文献：
  名称：

  Pyranocoumarins: A new class of anti-hyperglycemic and anti-dyslipidemic agents

  摘要：

  A series of pyranocoumarin derivatives were synthesized and evaluated in vivo for their anti-hyperglycemic as well as anti-dyslipidemic activities. Compounds 7a, 7c, 8a, 8b, 8c, 8e and 8f have shown promising anti-hyperglycemic activities in sucrose loaded model (SLM) as well as sucrose challenged streptozotocin induced diabetic rat model (STZ). Compounds 8a and 8b were showing 38.0% and 42.0% blood glucose lowering activity in db/db mice model. In vitro anti-hyperglycemic activity evaluation exhibited that compounds 8a (IC50 = 24.5 mu M) and 8b (IC50 = 36.2 mu M) are potential PTP-1B inhibitors thereby revealing their possible mechanism of anti-diabetic action. Compounds 7a, 7b, 8a, 8b, 8d, 8e and 8f have shown significant anti-dyslipidemic activity in triton induced dyslipidemia in rats. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.031

文献信息

• Pyranocoumarins: A new class of anti-hyperglycemic and anti-dyslipidemic agents
  作者：Atul Kumar、Ram Awatar Maurya、Siddharth Sharma、Pervez Ahmad、A.B. Singh、Gitika Bhatia、Arvind K. Srivastava

  DOI：10.1016/j.bmcl.2009.09.031

  日期：2009.11

  A series of pyranocoumarin derivatives were synthesized and evaluated in vivo for their anti-hyperglycemic as well as anti-dyslipidemic activities. Compounds 7a, 7c, 8a, 8b, 8c, 8e and 8f have shown promising anti-hyperglycemic activities in sucrose loaded model (SLM) as well as sucrose challenged streptozotocin induced diabetic rat model (STZ). Compounds 8a and 8b were showing 38.0% and 42.0% blood glucose lowering activity in db/db mice model. In vitro anti-hyperglycemic activity evaluation exhibited that compounds 8a (IC50 = 24.5 mu M) and 8b (IC50 = 36.2 mu M) are potential PTP-1B inhibitors thereby revealing their possible mechanism of anti-diabetic action. Compounds 7a, 7b, 8a, 8b, 8d, 8e and 8f have shown significant anti-dyslipidemic activity in triton induced dyslipidemia in rats. (C) 2009 Elsevier Ltd. All rights reserved.