5,7-bis-benzyloxy-4-methyl-chromen-2-one | 17917-62-3

• 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: 5,7-bis-benzyloxy-4-methyl-chromen-2-one
• 英文别名: 5,7-Dibenzyloxy-4-methyl-cumarin；5,7-bis(benzyloxy)-4-methyl-2H-chromen-2-one；4-methyl-5,7-bis(phenylmethoxy)chromen-2-one
• CAS: 17917-62-3
• 化学式: C₂₄H₂₀O₄
• mdl: MFCD02080994
• 分子量: 372.42
• InChiKey: ZGPAVSFWWIHYMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,7-bis-benzyloxy-4-methyl-chromen-2-one 在 selenium(IV) oxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 20.0h， 生成 5,7-bis-benzyloxy-2-oxo-2H-chromene-4-carbaldehyde
  参考文献：
  名称：

  Synthesis and antioxidant activities of novel 4-Schiff base-7-benzyloxy-coumarin derivatives

  摘要：

  4-Schiff base-7-benzyloxy-coumarins 5a(1)-5h(2) and its derivative 6 were designed and synthesized based on the 7-benzyloxy-coumarin structure as novel antioxidants. The in vitro antioxidant activities screening revealed that 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of compounds 5b(1), 5d(1), 5f(1), 5f(2), 5g(1) and 5g(2), and 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation (ABTS(+)) radical scavenging activities of compounds 5a(1), 5b(1), 5c(1), 5c(2), 5d(1), 5e(1), 5e(2), 5f(2), 5g(1), 5g(2) and 5h(1) were better than that of the commercial antioxidant butylated hydroxytoluene (BHT), while the superoxide anion radical scavenging activities of 5a(2) and 5g(2) were stronger than that of the commercial antioxidant butylated hydroxyanisole (BHA), and the hydroxyl radical scavenging activity of 5e(1) was much better than that of the common antioxidant ascorbic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.029
• 作为产物：
  描述：

  间苯三酚 在 sodium hydrogensulfate monohydrate 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 18.0h， 生成 5,7-bis-benzyloxy-4-methyl-chromen-2-one
  参考文献：
  名称：

  Synthesis and antioxidant activities of novel 4-Schiff base-7-benzyloxy-coumarin derivatives

  摘要：

  4-Schiff base-7-benzyloxy-coumarins 5a(1)-5h(2) and its derivative 6 were designed and synthesized based on the 7-benzyloxy-coumarin structure as novel antioxidants. The in vitro antioxidant activities screening revealed that 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activities of compounds 5b(1), 5d(1), 5f(1), 5f(2), 5g(1) and 5g(2), and 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation (ABTS(+)) radical scavenging activities of compounds 5a(1), 5b(1), 5c(1), 5c(2), 5d(1), 5e(1), 5e(2), 5f(2), 5g(1), 5g(2) and 5h(1) were better than that of the commercial antioxidant butylated hydroxytoluene (BHT), while the superoxide anion radical scavenging activities of 5a(2) and 5g(2) were stronger than that of the commercial antioxidant butylated hydroxyanisole (BHA), and the hydroxyl radical scavenging activity of 5e(1) was much better than that of the common antioxidant ascorbic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.029

文献信息

• α-Glucosidase Inhibition, Antioxidant and Docking Studies of Hydroxycoumarins and their Mono and Bis O-alkylated/acetylated Analogs
  作者：Parvesh Singh、Nomandla Ngcoya、Ramgopal Mopuri、Nagaraju Kerru、Neha Manhas、Oluwakemi Ebenezer、Md. Shahidul Islam

  DOI：10.2174/1570180814666170602081941

  日期：2018.1.30

  -2-one (A9) bearing a benzyl group (Ph-CH2-) at position 7 showed a remarkable (p <0.05) increase in the activity (IC50 = 11.084±0.117 µg/mL), almost four-fold more than acarbose (IC50 = 40.578±5.999 µg/mL). The introduction of –NO2 group dramatically improved the anti-oxidant activity of coumarin, while the O-alkylation/acetylation decreased the activity. Conclusion: The present study describes the

  背景：糖尿病（DM）是一种复杂的代谢疾病，其血浆葡萄糖水平异常升高或高血糖。因此，已经开发出几种用于治疗糖尿病和其他变性疾病的α-葡萄糖苷酶抑制剂。同时，香豆素环具有代表具有广泛生物活性的多种天然和合成化合物的特权，例如抗癌，抗HIV，抗病毒，抗疟疾，抗微生物，抗惊厥，抗高血压属性。除此之外，香豆素还显示出抑制α-葡萄糖苷酶的潜力，从而导致了新的有希望的抗糖尿病药的产生。然而，O-取代的香豆素对α-葡萄糖苷酶抑制作用的测试已经避开了药物化学家的注意力。 方法：对于O-烷基化/乙酰化反应，在室温下在氮气下，将最初由K2CO3在干燥DMF中活化的羟基香豆素（AB）与各种取代的卤代烷烃反应。使用DPPH自由基清除活性测试合成的化合物的α-葡糖苷酶（来自酿酒酵母）的抑制活性和抗氧化活性。使用DS（Accelrys）中的CDocker模块进行计算机对接模拟，以探索代表性化合物在α-葡萄糖苷酶催化位点的结合模式。