Synthesis and characterization of halogenated bis(acylthiourea) derivatives and their antibacterial activities

Halim, Ainaa Nadiah Abd; Ngaini, Zainab

doi:10.1080/10426507.2017.1315421

Cited by 18 publications

(11 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…iourea is known as a versatile compound that has been intensely synthesised due to its ability to undergo structural modification [4]. Having two units of reactive primary amine group has led thiourea to be a suitable precursor for the synthesis of many derivatives in new compounds [5]. Oxygen, nitrogen, and sulphur atoms of thiourea derivatives provide a multitude of bonding possibilities that may contribute to a broad spectrum of thiourea applications in the pharmaceutical field, such as antiparasitic, anticancer, antioxidant, antibacterial, antifungal, antimalarial, and anti-HIV [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment

Misral

Sapari

Rahman

et al. 2018

Journal of Chemistry

View full text Add to dashboard Cite

Isomers of monothioureas, 2a–2d, derived from the reaction of disubstituted benzoyl isothiocyanate and dibenzylamine were synthesised and characterised by using elementary analysis CHNS and IR, 1H NMR, and 13C NMR spectroscopies. The compounds were screened for their in vitro antibacterial activity by using selected Gram-positive bacteria, and moderate inhibition activity was displayed for compound 2b with the value of inhibition zone 11 ± 0.8 mm at a concentration of 50 mg/ml. The outcomes of Lipinski’s rule of five assessment appeared to be in agreement with all compounds as they adhered to most of the rules, in which they can be preliminarily classified as active drug-like. The frontier molecular orbitals (HOMO and LUMO) for halogen-substituted 3,4-dichloro (2a) and 3,4-difluoro (2b) were also determined by applying the computational method of density functional theory (DFT) to determine their relationship as a molecular descriptor in antibacterial activities. The value of LUMO energy for compound 2b (1.8229 eV) is lower than that of compound 2a (1.8492 eV) which indicates higher antibacterial activities.

show abstract

Section: Introductionmentioning

confidence: 99%

Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment

Misral

Sapari

Rahman

et al. 2018

Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…The transmittance (T) was recorded using UV–Visible Spectrophotometer Optima SP‐300, Japan after 1 h interval. The antibacterial activity was examined by plotting graph of ln Nt vs. time which the ln Nt value describe the number of colony‐forming units/mL 29 …”

Section: Antibacterial Studymentioning

confidence: 99%

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Farooq

Ngaini

Mortadza

2020

Bulletin Korean Chem Soc

Self Cite

View full text Add to dashboard Cite

In this study, a series of chalcone derivatives (1a-c) were synthesized via Claisen-Schmidt condensation, followed by aza-Michael addition to form pyrazoline derivatives (2a-c and 3a-c). The reaction was performed via microwave radiation to give excellent yields (77-93%) in 1-3.5 min. Microwave-assisted reaction of Fischer esterification of pyrazolines (2a-c and 3a-c) afforded heteroaromatic pyrazoline esters (4a-c) in high yield (83-96% in <2 min) compared to conventional reflux (55-79% in 30 min). Compounds 1a-c and 3a-c demonstrated excellent antibacterial activity against Staphylococcus aureus via disc diffusion assay with inhibition zone with 13 and 19 mm compared to a standard drug, ampicillin (11 mm). Structure activity relationship of 1b and 3b were visualized via molecular docking interaction against 4pql protein of S. aureus with binding free energy −7.0 and −8.0 kcal/mol, respectively. This study is significant in drug discovery process particularly for pharmaceutical industries.

show abstract

“…[36] The outcomes were allocated into three groups, mild (6-13 mm), moderate (14-16 mm), or strong (> 17 mm). [37] The relative studies were conducted for the inhibition of S. aureus and E. coli by comparing zone of inhibition of the synthesized compounds with inhibition zone of standard drug.…”

Section: Biological Activitiesmentioning

confidence: 99%

“…The synthesized compounds experienced poor solubility [6,44] and dissolution of compounds during administration into the assay that lead to precipitation of the vehicle-insoluble particles. [37] This phenomenon has caused interference for a quantitative determination of the biological activities. Due to this phenomenon, Kirby Bauer disc diffusion method was therefore chosen for further keto-exchange studies and molecular docking.…”

Section: Biological Activitiesmentioning

confidence: 99%

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

Farooq

Ngaini

2020

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

Bacterial diseases cause hazardous infections due to the occurrence of bacterial resistance. Drugs production to cure bacterial resistance from natural sources has become ineffective to execute the resisted bacteria due to the unsuitable binding interaction of active sites with the receptors. Drug link to natural products moieties such as chalcones and pyrazolines, which originated from plants extracts, has become attractive among researchers due to its significant pharmaceutical moiety. In this study a series of chalcone derivatives (1 a–d) has been synthesized via Claisen‐Schmidt condensation, followed by cyclization to form pyrazolines (2 a–d, 3 a–d). Fischer esterification of pyrazolines formed 4 a–d in moderate to good yield (42.91‐88.23 %). Antimicrobial activities of all the synthesized compounds were evaluated against Escherichia coli and Staphylococcus aureus via disc diffusion. Among all compounds, pyrazolines 3 c and 3 d showed the highest zone of inhibition (17 mm) compared to 1 a‐d (5‐11 mm) and standard ampicillin (11 mm). The exchange of α, β‐unsaturated carbonyl showed phenomenal increment in the biological activities. Structure activity relationship of 1 a, 1 d, 3 a and 3 d was analyzed via molecular docking of N‐terminal domain having deoxyribonucleic acid (DNA) binding protein (4pql) with excellent binding energy of −6.2, −6.6, −7.1 and −7.2 kcal/mol, respectively. This work is significant in designing new drugs with keto‐exchange relationship for medicinal industry.

show abstract

Synthesis and characterization of halogenated bis(acylthiourea) derivatives and their antibacterial activities

Cited by 18 publications

References 26 publications

Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment

Evaluation of Novel N-(Dibenzylcarbamothioyl)benzamide Derivatives as Antibacterial Agents by Using DFT and Drug-Likeness Assessment

Microwave‐assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents

Synthesis, Molecular Docking and Antimicrobial Activity of α, β‐Unsaturated Ketone Exchange Moiety for Chalcone and Pyrazoline Derivatives

Contact Info

Product

Resources

About