El-Desoky El-Sayed I, Keshk Eman M, El-Sawi Aya A, Abozeid Mohamed A, Abouzeid Laila A, Abdel-Rahman Abdel-Rahman H
Department of Chemistry, Faculty of Science, Mansoura University, El-Gomhoria St., Mansoura 35516, Egypt.
Department of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, El-Gomhoria Street, Mansoura 35516, Egypt.
Saudi Pharm J. 2018 Sep;26(6):852-859. doi: 10.1016/j.jsps.2018.03.013. Epub 2018 Mar 27.
The versatile precursor 2-acetyl-4-allyl-1-hydroxy naphthalene was synthesized efficiently via Claisen rearrangement 2-acetyl-1-allyloxynaphthalene. The Claisen-Schmidt condensation of latter precursor afforded the corresponding chalcones which were exploited to synthesize a series of potential heterocycles such as pyrazoline, isoxazoline, benzocoumarin and benzoflavone. The synthesized products showed potent antioxidant and antimicrobial activities. Chalcone , naphthyl pyrazoline and hydroxycoumarin exhibited the highest activity as antioxidants. Their binding mode showed specialized recognition of hydroxycoumarin with the triad key amino acids at the active site of the oxidoreductase enzyme (PDB code 1DXO). 1-Hydroxynaphth-2-yl pyrazoline () revealed the highest efficacy against both Gram positive and negative bacterial species. molecular docking of pyrazoline endorsed its proper binding at the active site of the 2EX6 enzyme which explains its potent antibacterial activity in comparison with standard ampicillin.
通过克莱森重排2-乙酰基-1-烯丙氧基萘高效合成了多功能前体2-乙酰基-4-烯丙基-1-羟基萘。后一种前体的克莱森-施密特缩合反应得到了相应的查尔酮，利用这些查尔酮合成了一系列潜在的杂环化合物，如吡唑啉、异恶唑啉、苯并香豆素和苯并黄酮。合成产物表现出强大的抗氧化和抗菌活性。查尔酮、萘基吡唑啉和羟基香豆素作为抗氧化剂表现出最高的活性。它们的结合模式显示羟基香豆素与氧化还原酶（PDB代码1DXO）活性位点的三联体关键氨基酸有特异性识别。1-羟基萘-2-基吡唑啉对革兰氏阳性和阴性细菌均显示出最高的功效。吡唑啉的分子对接证实了其在2EX6酶活性位点的正确结合，这解释了其与标准氨苄青霉素相比具有强大的抗菌活性。
