5-(3-benzyloxy-4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 278781-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(3-benzyloxy-4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[(3-Benzyloxy-4-methoxy-phenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(4-methoxy-3-phenylmethoxyphenyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 278781-87-6
• 化学式: C₂₁H₂₀O₆
• 分子量: 368.386
• InChiKey: WIAUFPLOZUDZFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 3-苄氧基-4-甲氧基苯甲醛 以 甲醇 为溶剂， 生成 5-(3-benzyloxy-4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents

  摘要：

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.033

文献信息

• Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents
  作者：Harmeet S. Sandhu、Sameer Sapra、Mukesh Gupta、Kunal Nepali、Raju Gautam、Sunil Yadav、Raj Kumar、Sanjay M. Jachak、Manoj Chugh、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2010.06.033

  日期：2010.8

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.