Synthesis and structural study of some N-acyl-4-allylsemicarbazides and the product of their cyclization with a potential antimicrobial activity

Pitucha, Monika; Karczmarzyk, Zbigniew; Swatko-Ossor, Marta; Drozd, Monika; Wysocki, Waldemar; Ginalska, Grażyna; Urbańczyk‐Lipkowska, Zofia; Kowalczuk, Dorota; Morawiak, Maja

doi:10.1016/j.molstruc.2020.128552

Cited by 6 publications

(3 citation statements)

References 27 publications

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“…In the case of antimicrobial activity, several reports suggest structures with, at least, a frontier orbital located in a specific molecular region displaying a broad spectrum of activity [48][49][50][51][52][53][54][55][56][57], compared to compounds whose frontier orbitals are scattered in the whole structures. This latter characteristic is related to the compound fluorescence ability [58][59][60].…”

Section: Molecular Orbitalsmentioning

confidence: 99%

QSAR Studies, Molecular Docking, Molecular Dynamics, Synthesis, and Biological Evaluation of Novel Quinolinone-Based Thiosemicarbazones against Mycobacterium tuberculosis

et al. 2022

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In this study, a series of novel quinolinone-based thiosemicarbazones were designed in silico and their activities tested in vitro against Mycobacterium tuberculosis (M. tuberculosis). Quantitative structure-activity relationship (QSAR) studies were performed using quinolinone and thiosemicarbazide as pharmacophoric nuclei; the best model showed statistical parameters of R2 = 0.83; F = 47.96; s = 0.31, and was validated by several different methods. The van der Waals volume, electron density, and electronegativity model results suggested a pivotal role in antituberculosis (anti-TB) activity. Subsequently, from this model a new series of quinolinone-thiosemicarbazone 11a–e was designed and docked against two tuberculosis protein targets: enoyl-acyl carrier protein reductase (InhA) and decaprenylphosphoryl-β-D-ribose-2’-oxidase (DprE1). Molecular dynamics simulation over 200 ns showed a binding energy of −71.3 to −12.7 Kcal/mol, suggesting likely inhibition. In vitro antimycobacterial activity of quinolinone-thiosemicarbazone for 11a–e was evaluated against M. bovis, M. tuberculosis H37Rv, and six different strains of drug-resistant M. tuberculosis. All compounds exhibited good to excellent activity against all the families of M. tuberculosis. Several of the here synthesized compounds were more effective than the standard drugs (isoniazid, oxafloxacin), 11d and 11e being the most active products. The results suggest that these compounds may contribute as lead compounds in the research of new potential antimycobacterial agents.

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Section: Molecular Orbitalsmentioning

confidence: 99%

QSAR Studies, Molecular Docking, Molecular Dynamics, Synthesis, and Biological Evaluation of Novel Quinolinone-Based Thiosemicarbazones against Mycobacterium tuberculosis

et al. 2022

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“…The lower energy gap (ΔE) has a considerable impact on the intermolecular charge transfer and the bioactivity of compounds (30,31). Consequently, a lower energy gap observed in the compounds positively affects the electron to move from the HOMO to the LUMO, resulting in a good affinity for S. aureus.…”

Section: Dft Studies Resultsmentioning

confidence: 99%

Antimicrobial prospection and density functional study of some phenolic compounds

GABRIELA¹,

CRISTINA²,

MARIA³

2023

Acta Poloniae Pharmaceutica - Drug Research

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Phenols represent an important class of compounds that present high antimicrobial potential. The seventeen selected phenols were tested in vitro for their antimicrobial activity showing different activity to S. aureus ATCC 25923, E. coli ATCC 25922, P. aeruginosa ATCC 27853 and C. albicans ATCC 90028. Most of the phenolic compounds have a good efficacy on S. aureus and C. albicans. 2- and 4-aminophenol have been found to be the most potent antimicrobial agents against S. aureus, with MIC values 0.170 mg/mL and 0.340 mg/mL, respectively. The frontier orbital energy and the global reactivity descriptors (calculated using Spartan 16 software) were discussed for the selected phenols; results revealed that the theoretical calculations of antimicrobial activity were related to the quantum chemical parameters.

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“…38 They exhibit good antitumor and anti-diabetic activities. 8,10,23,39,40 In addition, some hydrazide derivatives were found to possess anti-inflammatory and analgesic activities. 41,42 To date, different procedures have been investigated for the synthesis of carbohydrazide.…”

Section: Introductionmentioning

confidence: 99%

Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

et al. 2023

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Synthesis and structural study of some N-acyl-4-allylsemicarbazides and the product of their cyclization with a potential antimicrobial activity

Cited by 6 publications

References 27 publications

QSAR Studies, Molecular Docking, Molecular Dynamics, Synthesis, and Biological Evaluation of Novel Quinolinone-Based Thiosemicarbazones against Mycobacterium tuberculosis

QSAR Studies, Molecular Docking, Molecular Dynamics, Synthesis, and Biological Evaluation of Novel Quinolinone-Based Thiosemicarbazones against Mycobacterium tuberculosis

Antimicrobial prospection and density functional study of some phenolic compounds

Green electro-organic synthesis of a novel catechol derivative based on o-benzoquinone nucleophilic addition

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