Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives

The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain.

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Synthesis, Biological Assessment, and Structure Activity Relationship Studies of New Flavanones Embodying Chromene Moieties

Molecules ◽

10.3390/molecules25030544 ◽

2020 ◽

Vol 25 (3) ◽

pp. 544 ◽

Cited By ~ 2

Author(s):

Eman Assirey ◽

Azhaar Alsaggaf ◽

Arshi Naqvi ◽

Ziad Moussa ◽

Rawda M. Okasha ◽

...

Keyword(s):

In Silico ◽

Biological Assessment ◽

Diffusion Method ◽

Breast Adenocarcinoma ◽

Cytotoxic Activities ◽

Human Pathogens ◽

Bacterial Strains ◽

Human Carcinoma ◽

In Silico Studies

Novel flavanones that incorporate chromene motifs are synthesized via a one-step multicomponent reaction. The structures of the new chromenes are elucidated by using IR, 1H-NMR, 13C-NMR, 1H-1H COSY, HSQC, HMBC, and elemental analysis. The new compounds are screened for their in vitro antimicrobial and cytotoxic activities. The antimicrobial properties are investigated and established against seven human pathogens, employing the agar well diffusion method and the minimum inhibitory concentrations. A majority of the assessed derivatives are found to exhibit significant antimicrobial activities against most bacterial strains, in comparison to standard reference drugs. Moreover, their cytotoxicity is appraised against four different human carcinoma cell lines: human colon carcinoma (HCT-116), human hepatocellular carcinoma (HepG-2), human breast adenocarcinoma (MCF-7), and adenocarcinoma human alveolar basal epithelial cell (A-549). All the desired compounds are subjected to in-silico studies, forecasting their drug likeness, bioactivity, and the absorption, distribution, metabolism, and excretion (ADME) properties prior to their synthetic assembly. The in-silico molecular docking evaluation of all the targeted derivatives is undertaken on gyrase B and the cyclin-dependent kinase. The in-silico predicted outcomes were endorsed by the in vitro studies.

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In silico, Physico-chemical characterization and analysis of Sandalwood proteins

International Journal of Agricultural Invention ◽

10.46492/ijai/2018.3.2.10 ◽

2018 ◽

Vol 3 (02) ◽

pp. 150-157

Author(s):

Asad Amir ◽

Neelesh Kapoor ◽

Hirdesh Kumar ◽

Mohd. Tariq ◽

Mohd. Asif Siddiqui

Keyword(s):

Secondary Structure ◽

In Silico ◽

Chemical Characterization ◽

In Silico Analysis ◽

Chemical Parameters ◽

Physico Chemical ◽

In Silico Studies ◽

The Family ◽

Silico Analysis

Sandalwood is a commercially and culturally important plant species belonging to the family Santalaceae and the genus Santalum. In Indian sandalwood is renowned for its oil, which is highly rated for its sweet, fragrant, persistent aroma and the fixative property which is highly demanded by the perfume industry. For better production and varieties, requires to understanding the functions of proteins, their analysis and characterization of proteins sequences and their structures, their localizations in cell and their interaction with other functional partner. Due to limited number of in silico studies on sandalwood, in the present study we have performed in silico analysis by characterization of sandalwood proteins. Total 23 proteins were obtained and characterization using UniProtKB, identifying their physico-chemical parameters using ProtParam tool and prediction of their secondary structure elements using GOR of all 23 proteins.

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MCF-7 Human Breast Adenocarcinoma Anticancer and Antimicrobial, in silico Docking and ADME Prediction Studies of Furan Moiety Containing Substituted 2-Aminopyrimidine Derivatives

Asian Journal of Chemistry ◽

10.14233/ajchem.2021.23186 ◽

2021 ◽

Vol 33 (7) ◽

pp. 1504-1512

Author(s):

Manju Mathew ◽

Muthuvel Ramanathan Ezhilarasi

Keyword(s):

In Silico ◽

Antimicrobial Activities ◽

Docking Studies ◽

Breast Adenocarcinoma ◽

Bacterial Strains ◽

In Silico Docking ◽

In Silico Studies ◽

Furan Moiety ◽

Different Strains

A series of 4(5-(4-chlorophenyl)furan-2-yl)-6-phenylpyrimidin-2-amine derivatives (5a-h) were synthesized from 2-(4-chlorophenyl)-5-styrylfuran (3a-h) with guanidine nitrate in absolute ethanol under conventional method and evaluated for their in vitro anticancer, antimicrobial activities and in silico studies. The chemical structure of the furan moiety containing substituted amino pyrimidine derivatives (5a-h) were elucidated from spectroscopic analysis like infrared, 1H & 13C NMR spectral data and CHN analysis. in silico docking studies were predicted for the synthesized compounds (5a-h) using bacterial protein 1UAG and in silico ADME predictions were also carried for the synthesized compounds (5a-h). The in vitro anticancer study was carried the compound 5b by MMT assay. Compound 5b shows the LC50 value of 120.15 ± 0.003 μg/mL. in vitro Antimicrobial activities were screened for the compounds (5a-h) using different strains. Compound 5h has electron withdrawing group in benzene ring substituted in the para position showed good antimicrobial activity against all the bacterial strains and fungal strains. in silico studies, compound 5h shows excellent docking score (-9.7 kcal/mol) compared with ciprofloxacin (-7.8 kcal/mol).

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Synthesis, Antimicrobial Evaluation and In silico Studies of Novel 2,4- disubstituted-1,3-thiazole Derivatives

Letters in Drug Design & Discovery ◽

10.2174/1570180815666180502120042 ◽

2018 ◽

Vol 16 (2) ◽

pp. 160-173 ◽

Cited By ~ 2

Author(s):

Mir Mohammad Masood ◽

Mohammad Irfan ◽

Shadab Alam ◽

Phool Hasan ◽

Aarfa Queen ◽

...

Keyword(s):

In Silico ◽

Bacterial Infections ◽

Antimicrobial Agents ◽

Docking Studies ◽

Bacterial Strains ◽

Thiazole Derivatives ◽

Standard Drug ◽

Hek 293 ◽

In Silico Studies

Background: 2,4-disubstituted-1,3-thiazole derivatives (2a–j), (3a–f) and (4a–f) were synthesized, characterized and screened for their potential as antimicrobial agents. In the preliminary screening against a panel of bacterial strains, nine compounds showed moderate to potent antibacterial activity (IC50 = 13.7-90.8 μg/ml). </P><P> Methods: In the antifungal screening, compound (4c) displayed potent antifungal activity (IC50 = 26.5 µg/ml) against Candida tropicalis comparable to the standard drug, fluconazole (IC50 = 10.5 µg/ml). Based on in vitro antimicrobial results, compounds 2f, 4c and 4e were selected for further pharmacological investigations. Hemolytic activity using human red blood cells (hRBCs) and cytotoxicity by MTT assay on human embryonic kidney (HEK-293) cells revealed non-toxic nature of the selected compounds (2f, 4c and 4e). To ascertain their possible mode of action, docking studies with the lead inhibitors (2f, 4c and 4e) were performed using crystal structure coordinates of bacterial methionine aminopeptidases (MetAPs), an enzyme involved in bacterial protein synthesis and maturation. Results: The results of in vitro and in silico studies provide a rationale for selected compounds (2f, 4c and 4e) to be carried forward for further structural modifications and structure-activity relationship (SAR) studies against these bacterial infections. Conclusion: The study suggested binding with one or more key amino acid residues in the active site of Streptococcus pneumoniae MetAP (SpMetAP) and Escherichia coli MetAP (EcMetAP). In silico physicochemical properties using QikProp confirmed their drug likeliness.

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Comparison between Citral and Pompia Essential Oil Loaded in Phospholipid Vesicles for the Treatment of Skin and Mucosal Infections

Nanomaterials ◽

10.3390/nano10020286 ◽

2020 ◽

Vol 10 (2) ◽

pp. 286 ◽

Cited By ~ 3

Author(s):

Iris Usach ◽

Elisabetta Margarucci ◽

Maria Letizia Manca ◽

Carla Caddeo ◽

Matteo Aroffu ◽

...

Keyword(s):

Antimicrobial Activity ◽

Essential Oil ◽

Essential Oils ◽

Human Keratinocytes ◽

Phospholipid Vesicles ◽

Citrus Limon ◽

Bacterial Strains ◽

Physico Chemical ◽

Health Promoting

Citrus species extracts are well known sources of bio-functional compounds with health-promoting effects. In particular, essential oils are known for their antibacterial activity due to the high content of terpenes. In this work, the steam-distilled essential oil from the leaves of Citrus limon var. pompia was loaded in phospholipid vesicles. The physico-chemical characteristics of the essential oil loaded vesicles were compared with those of vesicles that were loaded with citral, which is one of the most abundant terpenes of Citrus essential oils. The biocompatibility of the vesicles was assessed in vitro in human keratinocytes. Furthermore, the antimicrobial activity of the vesicles was tested while using different bacterial strains and a yeast: Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans, respectively. The vesicles were small in size (~140 nm), slightly polydispersed (PI ~ 0.31), highly negatively charged (~ −73 mV), and able to incorporate high amounts of essential oil or citral (E% ~ 86%). Pompia essential oil and citral exhibited antimicrobial activity against all of the assayed microorganisms, with P. aeruginosa being the least sensitive. Citral was slightly more effective than pompia essential oil against E. coli, S. aureus, and C. albicans. The incorporation of citral in vesicles improved its antifungal activity against C. albicans.

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Synthesis of Oxadiazolyl, Pyrazolyl and Thiazolyl Derivatives of Thiophene-2-Carboxamide as Antimicrobial and Anti-HCV Agents

The Open Medicinal Chemistry Journal ◽

10.2174/1874104501711010038 ◽

2017 ◽

Vol 11 (1) ◽

pp. 38-53 ◽

Cited By ~ 5

Author(s):

Ola H. Rizk ◽

Omaima G. Shaaban ◽

Abeer E. Abdel Wahab

Keyword(s):

Antimicrobial Activity ◽

Antimicrobial Activities ◽

Hcv Rna ◽

Bacterial Strains ◽

Low Concentration ◽

Oxadiazole Derivatives ◽

Polymerase Chain ◽

New Compounds ◽

Derivatives Of

Introduction: Three series of pyrazole, thiazole and 1,3,4-oxadiazole, derivatives were synthesized starting from 5-amino-4-(hydrazinocarbonyl)-3-methylthiophene-2-carboxamide (2). Methods: All compounds were investigated for their preliminary antimicrobial activity. They were proved to exhibit remarkable antimicrobial activity against Pseudomonas aeruginosa with insignificant activity towards Gram positive bacterial strains and fungi. Results: In-vitro testing of the new compounds on hepatitis-C virus (HCV) replication in hepatocellular carcinoma cell line HepG2 infected with the virus utilizing the reverse transcription polymerase chain reaction technique (RT-PCR) generally showed inhibition of the replication of HCV RNA (–) strands at low concentration, while, eight compounds; 3a, 6, 7a, 7b, 9a, 9b, 10a and 11b proved to inhibit the replication of HCV RNA (+) and (–) strands at very low concentration range 0.08-0.36 μg/mL. Conclusion: Compounds 7b and 11b displayed the highest anti-HCV and antimicrobial activities in this study.

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Antimicrobial activity of aroylhydrazone-based oxido vanadium(v) complexes: in vitro and in silico studies

New Journal of Chemistry ◽

10.1039/c5nj02594j ◽

2016 ◽

Vol 40 (3) ◽

pp. 2401-2412 ◽

Cited By ~ 31

Author(s):

S. Yousef Ebrahimipour ◽

Iran Sheikhshoaie ◽

Jim Simpson ◽

Hadi Ebrahimnejad ◽

Michal Dusek ◽

...

Keyword(s):

Antimicrobial Activity ◽

In Silico ◽

In Silico Studies

A series of oxido vanadium(v) complexes have been synthesized and evaluated from the point of experimental and theoretical antimicrobial activity.

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Solvent-Free Synthesis, In Vitro and In Silico Studies of Novel Potential 1,3,4-Thiadiazole-Based Molecules against Microbial Pathogens

Molecules ◽

10.3390/molecules27020342 ◽

2022 ◽

Vol 27 (2) ◽

pp. 342

Author(s):

Ihsan A. Shehadi ◽

Mohamad T. T. Abdelrahman ◽

Mohamed Abdelraof ◽

Huda R. M. Rashdan

Keyword(s):

Antimicrobial Activity ◽

In Silico ◽

Docking Study ◽

Antimicrobial Activities ◽

Trna Synthetase ◽

Microbial Pathogens ◽

Molecular Docking Study ◽

Chemical Structures ◽

In Silico Studies

A new series of 1,3,4-thiadiazoles was synthesized by the reaction of methyl 2-(4-hydroxy-3-methoxybenzylidene) hydrazine-1-carbodithioate (2) with selected derivatives of hydrazonoyl halide by grinding method at room temperature. The chemical structures of the newly synthesized derivatives were resolved from correct spectral and microanalytical data. Moreover, all synthesized compounds were screened for their antimicrobial activities using Escherichia coli, Pseudomonas aeruginosa, Proteus vulgaris, Bacillus subtilis, Staphylococcus aureus, and Candida albicans. However, compounds 3 and 5 showed significant antimicrobial activity against all tested microorganisms. The other prepared compounds exhibited either only antimicrobial activity against Gram-positive bacteria like compounds 4 and 6, or only antifungal activity like compound 7. A molecular docking study of the compounds was performed against two important microbial enzymes: tyrosyl-tRNA synthetase (TyrRS ) and N-myristoyl transferase (Nmt). The tested compounds showed variety in binding poses and interactions. However, compound 3 showed the best interactions in terms of number of hydrogen bonds, and the lowest affinity binding energy (–8.4 and –9.1 kcal/mol, respectively). From the in vitro and in silico studies, compound 3 is a good candidate for the next steps of the drug development process as an antimicrobial drug.

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Novel Triazine Centred Manganese Based Complex: A Photophysical and Biological Studies

Asian Journal of Chemistry ◽

10.14233/ajchem.2020.22302 ◽

2019 ◽

Vol 32 (1) ◽

pp. 91-94

Author(s):

L. Alphonse ◽

P. Tharmaraj ◽

B. Avila Josephine ◽

V. Mary Teresita

Keyword(s):

Antimicrobial Activity ◽

Metal Complex ◽

Diffusion Method ◽

Bacterial Strains ◽

Fluorescent Properties ◽

E Coli ◽

Physico Chemical ◽

Biological Studies ◽

Ft Ir

In this work, Mn(II) complex of triazine based ligand has been synthesized and characterized using various physico-chemical methods including C,H,N elemental analysis, FT-IR, 1H NMR and EI-mass analysis. The synthesized compounds serve as potential photoactive material as indicated from its characteristic fluorescent properties. The ligand and its metal complex were assayed for in vitro antimicrobial activity on four bacterial strains (S. aureus, B. subtilis, E. coli and K. pneumoniae) using well-diffusion method and it was observed that metal complex showed enhanced antimicrobial activity against all tested strains as compared to ligand.

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Synthesis, antimicrobial evaluation and in silico studies of novel 3,4-disubstituted pyrrolidinesulfonamides

Chemical Bulletin of Kazakh National University ◽

10.15328/cb1044 ◽

2019 ◽

pp. 28-40

Author(s):

Badampudi Santosh Kumar ◽

Gudhi Madhu ◽

Lk Ravindranath

Keyword(s):

Antimicrobial Activity ◽

Active Site ◽

In Silico ◽

Glucosidase Inhibitors ◽

Docking Method ◽

In Silico Studies ◽

Antimicrobial Evaluation ◽

Antibacterial And Antifungal ◽

Free Energy Of Binding

3,4-Disubstituted pyrrolidinesulfonamides were synthesized and screened for their antimicrobial activity. Title compounds were established as potent antibacterial and antifungal agents. Noteworthy antimicrobial activity was found for the title compounds against the tested microorganisms. They exhibit comparable results with standard drugs. Besides the in vitro antimicrobial activity, the synthesized compounds were evaluated for their in silico inhibitory activity on active site of β-glucosidase enzyme. In silico studies were done by GOLD docking method against β-glucosidase 3VKK (PDB Id). In silico studies were conducted to evaluate the ability of synthesized compounds to inhibit the β-glucosidase enzyme. The results revealed that 3,4-disubstitutedpyrrolidinesulfonamides are the potent β-glucosidase inhibitors by binding at the active site. A sensible inhibition against β-glucosidases was observed for the compound with 13,4-oxadizole ring has higher β-glucosidase inhibition activity than the other compounds. The free energy of binding and inhibition constant (Ki) of the docked compounds were evaluated and presented.

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