Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.
Department of Pure Chemistry, Faculty of Chemistry, Shahid Beheshti University, G.C., Tehran, Iran.
Bioorg Chem. 2020 Oct;103:104139. doi: 10.1016/j.bioorg.2020.104139. Epub 2020 Jul 25.
4-Hydroxycoumarins represents an important structural motif in life sciences molecules with remarkable biological properties. 4-Hydroxycoumarins are important precursors in the synthesis of organic compounds and critical pharmacophores in medicinal chemistry. One of the derivatives of this compound is biscoumarin, which has anticoagulant medicinal properties. Porcine pancreas lipase (PPL) has been used as an efficient green biocatalyst for the synthesis of bis-4-hydroxycoumarin compounds and expands the biocatalytic promiscuity of lipase in organic synthesis. Some aromatic aldehydes have been used in this investigation for screening and examining the ability of enzyme in knoevenagel condensation. Various parameters including temperature, solvent, and the amount of biocatalyst were investigated, ethanol, 45 °C and 10 mg of PPL gave rise to best yields. Bis-4-hydroxy coumarin compounds were synthesized under mild reaction conditions with high conversion yields (81-88%).
4-羟基香豆素是生命科学分子中重要的结构基序，具有显著的生物学特性。4-羟基香豆素是合成有机化合物的重要前体，也是药物化学中的关键药效团。该化合物的一种衍生物是双香豆素，具有抗凝药物特性。猪胰脂肪酶（PPL）已被用作合成双-4-羟基香豆素化合物的高效绿色生物催化剂，并扩展了脂肪酶在有机合成中的生物催化多功能性。本研究中使用了一些芳香醛来筛选和检验酶在Knoevenagel 缩合反应中的能力。考察了各种参数，包括温度、溶剂和生物催化剂的用量，结果表明，乙醇、45°C 和 10mg 的 PPL 可获得最佳产率。双-4-羟基香豆素化合物在温和的反应条件下合成，转化率高（81-88%）。
