CinnaGen Medical Biotechnology Research Center, Alborz University of Medical Sciences, Karaj, Iran.
School of Chemical Engineering, College of Engineering, University of Tehran, Tehran, Iran.
Chem Biodivers. 2022 Jul;19(7):e202100964. doi: 10.1002/cbdv.202100964. Epub 2022 Jun 8.
Tyrosinase plays a pivotal role in the hyperpigmentation and enzymatic browning of fruit and vegetable. Therefore, tyrosinase inhibitors can be of interest in industries as depigmentation compounds as well as anti-browning agents. In the present study, a series of chlorophenylquinazolin-4(3H)-one derivative were rationally designed and synthesized. The formation of target compounds was confirmed by spectral characterization techniques such as IR, H-NMR, C-NMR, and elemental analysis. Among the synthesized derivatives, compound 8l was proved to be the most potent inhibitor with an IC value of 25.48±1.19 μM. Furthermore, the results of the molecular docking study showed that this compound fitted well in the active site of tyrosinase with the binding score of -10.72.
酪氨酸酶在水果和蔬菜的过度色素沉着和酶促褐变中起着关键作用。因此,酪氨酸酶抑制剂可以作为脱色化合物和抗褐变剂在工业中引起关注。在本研究中,合理设计并合成了一系列氯代苯并喹唑啉-4(3H)-酮衍生物。通过光谱特征技术,如 IR、H-NMR、C-NMR 和元素分析,确认了目标化合物的形成。在所合成的衍生物中,化合物 8l 被证明是最有效的抑制剂,IC 值为 25.48±1.19 μM。此外,分子对接研究的结果表明,该化合物与酪氨酸酶的活性位点结合良好,结合评分为-10.72。