(E)-1-(β-cellobiosyl)-4-(2-naphthyl)but-3-en-2-one | 1164131-59-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(β-cellobiosyl)-4-(2-naphthyl)but-3-en-2-one
• 英文别名: (E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-(2-napthyl)but-3-en-2-one；(E)-1-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]-4-naphthalen-2-ylbut-3-en-2-one
• CAS: 1164131-59-2
• 化学式: C₂₆H₃₂O₁₁
• 分子量: 520.533
• InChiKey: GOMSLUFQDBATST-SJQYXZEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (E)-1-(β-cellobiosyl)-4-(2-naphthyl)but-3-en-2-one 在 potassium tert-butylate 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 0.5h， 生成 6-[(β-cellobiosyl)methyl]-3-cyano-4-(2'-napthyl)pyridone
  参考文献：
  名称：

  新型吡喃糖基均-C-核苷的便捷合成及其抗糖尿病活性。

  摘要：

  通过在t-BuOK存在下丁烯酰基C-糖苷（5a-5j和8）与氰基乙酰胺的反应，然后进一步修饰，合成了一系列吡喃糖基-C-核苷。该反应通过将氰基乙酰胺迈克尔加成到丁烯酰基C-糖苷中，然后进行脱水环化和氧化芳构化而得到糖基甲基吡啶酮（6a-6j，7a-7j，9和10）。与POCl（3）在回流下反应的糖基甲基吡啶酮（6a-6e）以良好的产率得到了相应的糖基甲基吡啶（11a-11e和12a-12e）。筛选合成的化合物的体外α-葡萄糖苷酶，葡萄糖-6-磷酸酶和糖原磷酸化酶抑制活性。吡啶甲基甲基-C-核苷之一，化合物11d，

  DOI：

  10.1016/j.carres.2011.03.006
• 作为产物：
  描述：

  (E)-1-(2',3',6',2'',3'',4'',6''-hepta-O-acetyl-β-cellobiosyl)-4-(2-naphthyl)but-3-en-2-one 在 甲醇 、 sodium methylate 作用下， 以74%的产率得到(E)-1-(β-cellobiosyl)-4-(2-naphthyl)but-3-en-2-one
  参考文献：
  名称：

  Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity

  摘要：

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.136

文献信息

• A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities
  作者：Surendra Singh Bisht、Natasha Jaiswal、Anindra Sharma、Seerat Fatima、Rahul Sharma、Neha Rahuja、A.K. Srivastava、Vikas Bajpai、Brijesh Kumar、Rama P. Tripathi

  DOI：10.1016/j.carres.2011.03.006

  日期：2011.7

  A series of pyranosyl homo-C-nucleosides have been synthesized by reaction of butenonyl C-glycosides (5a-5j, and 8) and cyanoacetamide in presence of t-BuOK followed by further modifications. The reaction proceeds by Michael addition of cyanoacetamide to the butenonyl C-glycosides and subsequent dehydrative cyclization and oxidative aromatization to give glycosylmethyl pyridones (6a-6j, 7a-7j, 9, and

  通过在t-BuOK存在下丁烯酰基C-糖苷（5a-5j和8）与氰基乙酰胺的反应，然后进一步修饰，合成了一系列吡喃糖基-C-核苷。该反应通过将氰基乙酰胺迈克尔加成到丁烯酰基C-糖苷中，然后进行脱水环化和氧化芳构化而得到糖基甲基吡啶酮（6a-6j，7a-7j，9和10）。与POCl（3）在回流下反应的糖基甲基吡啶酮（6a-6e）以良好的产率得到了相应的糖基甲基吡啶（11a-11e和12a-12e）。筛选合成的化合物的体外α-葡萄糖苷酶，葡萄糖-6-磷酸酶和糖原磷酸化酶抑制活性。吡啶甲基甲基-C-核苷之一，化合物11d，
• Synthetic studies in butenonyl C-glycosides: Preparation of polyfunctional alkanonyl glycosides and their enzyme inhibitory activity
  作者：Surendra Singh Bisht、Seerat Fatima、Akhilesh K. Tamrakar、Neha Rahuja、Natasha Jaiswal、Arvind K. Srivastava、Rama P. Tripathi

  DOI：10.1016/j.bmcl.2009.03.136

  日期：2009.5

  A simple synthesis of phenyl butenoyl C-glycosides has been achieved by Aldol condensation of peracetylated glycosyl acetones with aromatic aldehydes followed by deacetylation with methanolic NaOMe. The selected butenoyl C-glycosides on conjugate addition of diethyl malonate resulted in polyfunctional alkanonyl glycosides in good yields. The butenoyl C- and alkanoyl C- glycosides were evaluated for their alpha-glucosidase, glucose-6-phosphatse and glycogen phosphorylase enzyme inhibitory activities in vitro. Three of the synthesized (3, 5 and 9) showed potent enzyme inhibitory activities as compared to standard drugs. Compounds 3, 5 and 9 were evaluated in vivo too displaying significant activity as compared to standard drugs acarbose and metformin. (C) 2009 Elsevier Ltd. All rights reserved.