Rational Design, Synthesis, <i>in Vitro</i>, and <i>in Silico</i> Studies of Chlorophenylquinazolin‐4(3<i>H</i>)‐One Containing Different Aryl Acetohydrazides as Tyrosinase Inhibitors
Mirhamed Hajimiri, Mohammad Khosravikia, Mehdi Khoshneviszadeh, Keyvan Pedrood, Seyedeh Zahra Hosseini, Mohammad Asgari, Somayeh Pirhadi, Mahshid Attarroshan, Koroush Mobaraki, Samanesadat Hosseini, Hossein Behnammanesh, Mahmood Biglar, Somayeh Karimian, Hossein Rastegar, Haleh Hamedifar, Bagher Larijani, Mohammad Mahdavi, Aida Iraji
Abstract
Abstract 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(3 H )‐one derivative were rationally designed and synthesized. The formation of target compounds was confirmed by spectral characterization techniques such as IR, 1 H‐NMR, 13 C‐NMR, and elemental analysis. Among the synthesized derivatives, compound 8l was proved to be the most potent inhibitor with an IC 50 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.