Crystal structure, Hirshfeld surface analysis, DFT and molecular docking studies on benzohydrazide derivatives as potential inhibitors of prostate cancer

Arjun, H. A.; Rajan, Ravi Kumar; Elancheran, R.; Ramanathan, Meena; Bhattacharjee, Atanu; Kabilan, S.

doi:10.1016/j.cdc.2020.100350

Cited by 31 publications

(2 citation statements)

References 25 publications

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“…In recent years, various hybrid derivatives have been reported for antimicrobial activity [9] . Benzohydrazides are widely used in drug design because of various pharmacological properties such as α‐glucosidase and α‐amylase inhibitory, [10] anti‐cancer, [11] urease activity, [12] anti‐inflammatory, anti‐allergic, [13] and antioxidant activity [14] . Ansari et al.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

Sadeghian,

Zare,

Goshtasbi

et al. 2023

ChemistrySelect

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A new class of 3‐hydroxypyridine‐4‐one derivatives was synthesized and screened against several Gram‐positive and Gram‐negative bacteria, as well as two species of fungi. Among these synthesized compounds, the substituted derivatives with ortho‐ and para‐nitro and para‐methoxy groups showed the highest antibacterial activities against S. aureus and E. coli species with MIC value of 32 μg/mL, which were more potent compared to ampicillin as a reference drug. Furthermore, the substituted derivatives with ortho‐methoxy, ortho‐, para‐chloride, ortho‐, and para‐hydroxy groups exhibited MIC values of 64 μg/mL against S. aureus and E. coli species. In addition, the synthesized compounds were evaluated for their antifungal activities against C. albicans and A. niger strains. The best antifungal activity was observed for compounds with ortho‐methoxy, ortho‐hydroxy, and para‐methyl substitutions against A. niger species with MIC values of 64 μg/mL. The analysis of the antimicrobial results revealed that the type and position of the phenyl ring substituents greatly influence the antimicrobial activities of the synthesized compounds. Subsequently, molecular docking studies on E. coli species were performed to predict the interaction mode of these compounds in the active site of the receptor. Also, in silico ADME profile outputs showed that the compounds comply with the rule of five.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

Sadeghian,

Zare,

Goshtasbi

et al. 2023

ChemistrySelect

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“…With this variability, hydrazide-hydrazones are considered to be important starting molecules in the organic synthesis in addition to having other properties such as biological activity. [8][9][10] Molecular docking studies were carried out to determine the binding mode of the compounds with a representative COX-2 enzyme. The docking predictions were validated by a long run of molecular dynamics simulations that pointed to the formation of strong and stable complexes as the simulation time proceeded.…”

mentioning

confidence: 99%

Synthesis, crystal structure investigation and computational approach to discover potential hydrazide derivatives as a potent inhibitor of cyclooxygenase‐2 enzyme

Bakri

Mohamed

Ahmad

et al. 2022

J Biochem & Molecular Tox

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This study reports the synthesis of two new hydrazide derivatives, namely, (E)‐N′‐(4‐ bromobenzylidene)−2‐(4‐isobutylphenyl)propanehydrazide (4a) and (E)‐N′‐benzylidene‐2‐(4‐isobutylphenyl)propanehydrazide (4b), respectively. The compounds were synthesized by the reaction of benzaldehyde with Ibuprofen acid hydrazide. Their structures were confirmed by X‐ray crystallography. To try to do a more detailed investigation, computational studies including Hirshfeld surface analyses, energy frameworks, density functional theory (DFT) optimizations, frontier orbital analyses, molecular electrostatic potential analyses, and natural bond orbital analyses of the studied compounds are performed. Moreover, molecular docking and dynamics simulations of complexes of the compounds with the cyclooxygenase‐2 (COX‐2) enzyme were performed to determine the anti‐inflammatory potential of the compounds. These analyses predicted the compounds to show maximum chemical interactions and be dynamically stable during simulation time. Furthermore, estimation of binding free energies confirmed the high binding affinity of the compounds for the COX‐2 enzyme.

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Synthesis and biological activity of amide derivatives derived from natural product Waltherione F

et al. 2022

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Structural optimization based on natural products has become an effective way to develop new green fungicides, which provide important guiding signi cance for practicing the new development concept and promoting the green development of pesticides. In this project, combined with the fungicidal amide lead compound X-I-4 discovered in our previous work and fungicidal piperazine derivatives reported in literatures, the target compounds containing 4-quinolone and piperazine substructures based on waltherione F were designed, synthesized and screened for their biological activity. The bioassay results indicated that compounds I-3, I-5, II-3, II-7, II-10, II-11 and II-13 displayed higher inhibition rates against Rhizoctonia solani than other tested compounds. The in vitro cellular cytotoxicity assay revealed the compounds II-6 and II-11 exhibited higher cytotoxicity against HepG2 than other tested compounds. The uorescence characteristics investigation showed that the absolute uorescence QY value of the methanol solution of the compound I-6 was higher than those of I-2, I-3, I-7 and I-8, which was further elucidated by TD-DFT.

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Crystal structure, Hirshfeld surface analysis, DFT and molecular docking studies on benzohydrazide derivatives as potential inhibitors of prostate cancer

Cited by 31 publications

References 25 publications

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

Synthesis, Antimicrobial Evaluation, Molecular Docking, and ADME Studies of Some Novel 3‐Hydroxypyridine‐4‐one Derivatives

Synthesis, crystal structure investigation and computational approach to discover potential hydrazide derivatives as a potent inhibitor of cyclooxygenase‐2 enzyme

Synthesis and biological activity of amide derivatives derived from natural product Waltherione F

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