Design, Synthesis, Crystal Structure, In Vitro and In Silico Evaluation of New N′-Benzylidene-4-tert-butylbenzohydrazide Derivatives as Potent Urease Inhibitors

Background: Hydrazides play a vital role in making biologically active compounds in various fields of chemistry. These determine antioxidant, antidepressant, antimalarial, anti-inflammatory, antiglycating, and antimicrobial activity. In the present study, twenty-three new N′ benzylidene-4-(tert-buty...

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Vydáno v:Molecules (Basel, Switzerland) Ročník 27; číslo 20; s. 6906
Hlavní autoři: Ahmad, Sajjad, Khan, Momin, Rehman, Najeeb Ur, Ikram, Muhammad, Rehman, Sadia, Ali, Mahboob, Uddin, Jalal, Khan, Ajmal, Alam, Aftab, Al-Harrasi, Ahmed
Médium: Journal Article
Jazyk:angličtina
Vydáno: Basel MDPI AG 14.10.2022
MDPI
Témata:
4-(tert-butyl)benzohydrazide
Amino acids
Crystal lattices
Crystal structure
Enzymes
Hydrogen
in vitro
Ligands
SAR
synthesis
urease inhibition
ISSN:1420-3049, 1420-3049
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Shrnutí:Background: Hydrazides play a vital role in making biologically active compounds in various fields of chemistry. These determine antioxidant, antidepressant, antimalarial, anti-inflammatory, antiglycating, and antimicrobial activity. In the present study, twenty-three new N′ benzylidene-4-(tert-butyl)benzohydrazide derivatives (4–26) were synthesized by the condensation of aromatic aldehydes and commercially available 4-(tert-butyl)benzoic acid. All the target compounds were successfully synthesized from good to excellent yield; all synthesized derivatives were characterized via spectroscopic techniques such as HREI-MS and 1H-NMR. Synthesized compounds were evaluated for in vitro urease inhibition. All synthesized derivatives demonstrated good inhibitory activities in the range of IC50 = 13.33 ± 0.58–251.74 ± 6.82 µM as compared with standard thiourea having IC50 = 21.14 ± 0.425 µM. Two compounds, 6 and 25, were found to be more active than standard. SAR revealed that electron donating groups in phenyl ring have more influence on enzyme inhibition. However, to gain insight into the participation of different substituents in synthesized derivatives on the binding interactions with urease enzyme, in silico (computer simulation) molecular modeling analysis was carried out.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules27206906