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Synthesis, Crystal Structure, Biological Evaluation and in Silico Studies on Novel ( E )‐1‐(Substituted Benzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone Derivatives
Author(s) -
Qi Fan,
Qi Qianqian,
Song Jirong,
Huang Jie
Publication year - 2021
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.202000804
Subject(s) - semicarbazone , chemistry , intramolecular force , hydrogen bond , molecule , intermolecular force , crystal structure , stereochemistry , proton nmr , crystallography , organic chemistry
A series of ( E )‐1‐(substituted benzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone derivatives were synthesized and characterized by FT‐IR spectrum, elemental analysis, NMR spectrum, HR‐MS spectrum, and X‐ray single crystal diffraction technology. The crystal structures and packing of ( E )‐1‐(4‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone and ( E )‐1‐(3‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone were maintained through the intramolecular hydrogen bond (N3‐H6⋅⋅⋅N1) and intermolecular hydrogen bonds (N2‐H4⋅⋅⋅S1, C14‐H14⋅⋅⋅F1 and C7‐H7⋅⋅⋅S1). The results obtained by employing the DPPH free radicals scavenging assay indicated that ( E )‐1‐(4‐methoxylbenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had a more significant antioxidant activity compared with other compounds. The results measured by adopting the disc diffusion method elucidated that ( E )‐1‐(4‐trifluoromethylbenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone possessed a more prominent antifungal activity than other compounds. Molecular docking showed that ( E )‐1‐(4‐chlorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had the highest affinity with receptor protein (1NMT). Moreover, the drug‐likeness characteristic, physicochemical properties, pharmacokinetic profiles, and bioactivity scores of all the compounds were predicted through in silico studies. The results illustrated that ( E )‐1‐(4‐fluorobenzylidene)‐4‐(3‐isopropylphenyl)thiosemicarbazone had the drug‐likeness characteristic and all the compounds were considered as moderately biological active molecules.