Synthesis and antimicrobial activity of aryldiazenyl/arylhydrazono pyrazoles

2021 ◽  
Vol 45 (11-12) ◽  
pp. 1093-1099
Author(s):  
Abdulrhman Alsayari ◽  
Yahya I Asiri ◽  
Abdullatif Bin Muhsinah ◽  
Mohd. Zaheen Hassan
Keyword(s):  
Active Site ◽  
Phenyl Ring ◽  
Antimicrobial Agents ◽  
Inhibitory Concentration ◽  
Docking Studies ◽  
Considerable Effect ◽  
Design Synthesis ◽  
Structure Activity ◽  
Antimicrobial Evaluation

We report the design, synthesis, and in vitro antimicrobial evaluation of functionalized pyrazoles containing a hydrazono/diazenyl moiety. Among these newly synthesized derivatives, 4-[2-(4-chlorophenyl)hydrazono]-5-methyl-2-[2-(naphthalen-2-yloxy)acetyl]-2,4-dihydro-3 H-pyrazol-3-one is a promising antimicrobial agent against Staphylococcus aureus (minimum inhibitory concentration 0.19 μg mL−1). Structure–activity relationship studies reveal that the electronic environment on the distal phenyl ring has a considerable effect on the antimicrobial potential of the hybrid analogues. Molecular docking studies into the active site of S. aureus dihydrofolate reductase also prove the usefulness of hybridizing a pyrazole moiety with azo and hydrazo groups in the design of new antimicrobial agents.

scholarly journals Design, Synthesis, and Anti-Bacterial Evaluation of Triazolyl-Pterostilbene Derivatives

2019 ◽  
Vol 20 (18) ◽  
pp. 4564 ◽  
Author(s):  
Kai-Wei Tang ◽  
Shih-Chun Yang ◽  
Chih-Hua Tseng
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Agents ◽  
Water Solubility ◽  
Inhibitory Concentration ◽  
Docking Studies ◽  
Design Synthesis ◽  
Global Challenge ◽  
Design And Synthesis ◽  
Structure Activity ◽  
Mrsa Infection

Staphylococcus aureus resistance to current antibiotics has become the greatest global challenge facing public health. The development of new antimicrobial agents is urgent and important and is needed to provide additional therapeutic options. In our previous study, we found out that pterostilbene exhibited potent antibacterial activity, especially against methicillin-resistant Staphylococcus aureus (MRSA). According to previous studies, 1,2,3-triazole, with the characteristic of increasing the interaction with the target readily and enhancing water solubility, were widely used in the approved anti-bacterial drugs. Therefore, these results attract our interest to use the structure of pterostilbene as a scaffold for the hybrid 1,2,3-triazole moiety to develop a novel anti-MRSA infection agent. In this study, we demonstrated the design and synthesis of a series of triazolylpterostilbene derivatives. Among these compounds, compound 4d exhibited the most potent anti-MRSA activity with a minimum inhibitory concentration (MIC) value of 1.2–2.4 μg/mL and a minimum bactericidal concentration (MBC) value of 19.5–39 μg/mL. The structure–activity relationship and antibacterial mechanism were investigated in this study. Molecular docking studies were carried out to verify and rationalize the biological results. In this study, the results confirmed that our design could successfully increase the inhibitory activity and specificity against MRSA. Compound 4d could be used as a candidate for anti-bacterial agents and in depth vivo studies should be further investigated.

scholarly journals Pyrazolobenzothiazine-based carbothioamides as new structural leads for the inhibition of monoamine oxidases: design, synthesis, in vitro bioevaluation and molecular docking studies

MedChemComm ◽  
2017 ◽  
Vol 8 (2) ◽  
pp. 452-464 ◽  
Author(s):  
Syed Mobasher Ali Abid ◽  
Sana Aslam ◽  
Sumera Zaib ◽  
Syeda Mahwish Bakht ◽  
Matloob Ahmad ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Active Site ◽  
Potent Inhibitor ◽  
Binding Mode ◽  
Docking Studies ◽  
Design Synthesis ◽  
Molecular Docking Studies ◽  
Monoamine Oxidases ◽  
Mao B

Binding mode of potent inhibitor (green) & cognate ligand (pink) in the active site of MAO-B.

scholarly journals "MONOSACCHARIDE DERIVATIVES: SYNTHESIS, ANTIMICROBIAL, PASS, ANTIVIRAL AND MOLECULAR DOCKING STUDIES AGAINST SARS-COV-2 MPRO INHIBITORS "

2021 ◽  
Vol 55 (5-6) ◽  
pp. 477-499
Author(s):  
FARHANA YASMIN ◽  
MOHAMMED R. AMIN ◽  
MOHAMMED A. HOSEN ◽  
MOHAMMED Z. H. BULBUL ◽  
SUJAN DEY ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Antimicrobial Agents ◽  
Direct Method ◽  
Quantum Chemical Study ◽  
Docking Simulation ◽  
Parent Drug ◽  
Chemical Study ◽  
Docking Studies ◽  
Antimicrobial Evaluation

Several carbohydrate-based drugs are currently being used to treat a number of diseases in humans worldwide. Thus, our research group has focused on the synthesis of new methyl α-D-mannopyranoside (MDM) derivatives and their antimicrobial evaluation through computational studies. A series of MDM derivatives (2-6) were synthesized through facile regioselective acylation, using the direct method affording 6-O-(3-chlorobenzoyl) derivatives. This isolated 6-O-derivative was further transformed to 2,3,4-tri-O-acyl derivatives, bearing a wide variety of functionalities in a single molecular framework. The structures of the newly designed molecules were elucidated with the aid of IR, 1H NMR, mass spectroscopy, and elemental analysis. The prediction of the activity spectra for the compounds (PASS) and their in vitro antimicrobial evaluation were performed, demonstrating them to be potential antimicrobial agents. The antimicrobial tests demonstrated that the compounds 3 and 5 were the most potent with the minimum inhibitory concentration (MIC) values, ranging from 0.312±0.01 to 1.25±0.03 mg/mL, and minimum bactericidal concentration (MBC) values, ranging from 0.625±0.02 to 2.50±0.05 mg/mL. A quantum chemical study was performed to calculate the thermodynamic, molecular orbital and electrostatic potential properties of the designed compounds. Molecular docking simulation was carried out against SARS-CoV-2 Mpro protein 7BQY and 6Y84 to investigate their binding energy and binding tactics with the viral protein, and better binding affinity than that of the parent drug was observed. Also, pharmacokinetic prediction revealed an improved drug-likeness profile for all MDM derivatives.

scholarly journals Anti-tick effect and cholinesterase inhibition caused by Prosopis juliflora alkaloids: in vitro and in silico studies

2020 ◽  
Vol 29 (2) ◽  
Author(s):  
Hélimar Gonçalves de Lima ◽  
Francianne Oliveira Santos ◽  
Acidália Carine Vieira Santos ◽  
Gisele Dias da Silva ◽  
Rafaela Jesus dos Santos ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Active Site ◽  
Inhibitory Concentration ◽  
Interaction Mechanism ◽  
Docking Studies ◽  
Prosopis Juliflora ◽  
Cholinesterase Inhibition ◽  
In Silico Studies ◽  
Pi Interactions

Abstract We investigated the in vitro acaricide activity of the methanolic extract (ME) and alkaloid-rich fraction (AF) of Prosopis juliflora on Rhipicephalus microplus and correlated this effect with acetylcholinesterase (AChE) inhibition. The acaricide activity was evaluated using adult and larval immersion tests. Also, we studied the possible interaction mechanism of the major alkaloids present in this fraction via molecular docking at the active site of R. microplus AChE1 (RmAChE1). Higher reproductive inhibitory activity of the AF was recorded, with effective concentration (EC50) four times lower than that of the ME (31.6 versus 121 mg/mL). The AF caused mortality of tick larvae, with lethal concentration 50% (LC50) of 13.8 mg/mL. Both ME and AF were seen to have anticholinesterase activity on AChE of R. microplus larvae, while AF was more active with half-maximal inhibitory concentration (IC50) of 0.041 mg/mL. The LC-MS/MS analyses on the AF led to identification of three alkaloids: prosopine (1), juliprosinine (2) and juliprosopine (3). The molecular docking studies revealed that these alkaloids had interactions at the active site of the RmAChE1, mainly relating to hydrogen bonds and cation-pi interactions. We concluded that the alkaloids of P. juliflora showed acaricide activity on R. microplus and acted through an anticholinesterase mechanism.

Design, Synthesis and Evaluation of Thiourea Derivatives as Antimicrobial and Antiviral Agents

2019 ◽  
Vol 16 (6) ◽  
pp. 618-624 ◽  
Author(s):  
Veerasamy Ravichandran ◽  
Sivadasan Shalini ◽  
Krishnan Suresh Kumar ◽  
Harish Rajak ◽  
Ram Kishore Agrawal
Keyword(s):  
Spectral Analysis ◽  
Antimicrobial Agents ◽  
Antiviral Agents ◽  
Drug Resistant ◽  
Design Synthesis ◽  
Thiourea Derivatives ◽  
Structure Activity ◽  
Antiviral Activities ◽  
Anti Hiv

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho- chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents

1,5-Benzodiazepine derivatives as potential antimicrobial agents: design, synthesis, biological evaluation, and structure–activity relationships

2015 ◽  
Vol 13 (19) ◽  
pp. 5497-5509 ◽  
Author(s):  
Lan-Zhi Wang ◽  
Xiao-Qing Li ◽  
Ying-Shuang An
Keyword(s):  
Antimicrobial Activity ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Structure Activity Relationships ◽  
Structure Activity ◽  
Benzodiazepine Derivatives

36 novel 1,5-benzodiazepine derivatives were synthesized and evaluated for their in vitro antimicrobial activity. The results revealed that most of the 1,5-benzodiazepine derivatives exhibited considerable potency against all of the tested strains.

Antimicrobial Evaluation of Indole-Containing Hydrazone Derivatives

2011 ◽  
Vol 66 (7-8) ◽  
pp. 340-344 ◽  
Author(s):  
Hanif Shirinzadeh ◽  
Nurten Altanlar ◽  
Nihal Yucel ◽  
Seckin Ozden ◽  
Sibel Suzen
Keyword(s):  
Phenyl Ring ◽  
Inhibitory Concentration ◽  
Multidrug Resistant ◽  
Antimicrobial Activities ◽  
Drug Resistant ◽  
Dilution Technique ◽  
Aureus Isolate ◽  
Microbial Infections ◽  
Antimicrobial Evaluation

There has been an increasing importance of drug-resistant pathogens in clinical microbiological and antibacterial research. Indoles and hydrazone-type compounds constitute important classes of compounds in the search for effective agents against multidrug-resistant microbial infections. In this study a series of 1-methylindole-3-carboxaldehyde hydrazone derivatives were evaluated for their in vitro antimicrobial activities using the two-fold serial dilution technique against Staphylococcus aureus, methicillin-resistant S. aureus, methicillinresistant S. aureus isolate, Escherichia coli, Bacillus subtilis, and Candida albicans. The minimum inhibitory concentration (MIC) of the test compounds and the reference standards sultamicillin, ampicillin, fluconazole, and ciprofloxacin was determined. All compounds possessed a broad spectrum of activity having MIC values of 6.25 - 100 μg/ml against the tested microorganisms. Aromaticity and disubstitution of the phenyl ring with especially fluorine and chlorine atoms were found to be significant for the antimicrobial activity

scholarly journals Design, Synthesis and Characterization of Thiophene Substituted Chalcones for Possible Biological Evaluation

2021 ◽  
pp. 55-79
Author(s):  
Mejo Joseph ◽  
S. Alaxander
Keyword(s):  
Antibacterial Activity ◽  
Antimicrobial Agents ◽  
Docking Studies ◽  
Biological Evaluation ◽  
Significant Activity ◽  
Design Synthesis ◽  
Future Design ◽  
In Vitro Antibacterial Activity ◽  
Glutathione S Transferases

Development of new antimicrobial agents is a better solution to rectify drug resistance problems in society. In this circumstances new functionalized sulphur bearing heterocyclic moiety were designed, synthesized and evaluated for their in vitro antibacterial activity. The present work encompasses the designing novel series of thiophene substituted analogous linked to para amino acetophenone and different aldehydes were successfully synthesized and biological activity was predicted using various computational software’s such as Chemsketch, Molinspiration, and admetSAR. Among the synthesized thiophene substituted chalcones T-IV-I and thiophene T-IV-B displayed significant activity against Streptococcus auresis. Compounds T-IV-J, T-IV-H and T-IV-C bearing sulphur moiety possess better activity against Staphylococcus aureus. Moreover T-IV-C and T-IV-J exhibits good antibacterial activity against E. coli and Pseudomonas aeruginosa. In general, most of the synthesized compounds exhibited remarkable antibacterial activity due to the presence of sulphur atom in the heterocyclic moieties as well as its lipophilic characters. Molecular docking studies indicated that the synthesized compounds are potent inhibitor of microsomal enzyme Glutathione-S-transferases (PDB ID: 1GNW) also find the different interacting residues, bond distanceand nature of bondingbetween the target and the ligand molecules. The results provide important information for the future design of more effective antibacterial agents.

scholarly journals Design, Synthesis and Antimicrobial Evaluation of Novel 2-Thiobenzimidazole Derivatives: in silico and in vitro Approach

2020 ◽  
Vol 32 (11) ◽  
pp. 2753-2762
Author(s):  
C. Naresh Babu ◽  
S. Triveni ◽  
M. Vijaya Jyothi ◽  
B. Yamuna ◽  
A. Yamini
Keyword(s):  
Antimicrobial Agents ◽  
Dna Gyrase ◽  
Docking Studies ◽  
Molecular Structures ◽  
Benzimidazole Derivatives ◽  
Design Synthesis ◽  
Lipinski’S Rule ◽  
Mass Spectral ◽  
Subunit B

The development of potent antimicrobial agents is more essential due to resistance developed in microorganisms towards the existing drugs. The diversity in the biological retort profile of benzimidazole more attracted the attention to develop novel compounds to its various potential against microorganisms. In present work, designed molecular structures docked against DNA gyrase subunit B and lanosterol 14α-demethylase (LAD) proteins. Interestingly, most of the compounds revealed excellent docking scores and interactions compared with the co-crystal ligands KKK, 1YN of LAD proteins 3LD6, 5V5Z than DNA gyrase subunit B proteins 5L3J and 4P8O. Then, the molecular properties were predicted by the Swiss ADME tool, the compounds showed no violation in Lipinski’s rule and good synthetic accessibility. These compounds synthesized by stirring of 2-mercapto benzimidazole (1), epichlorohydrin (2) in the presence of sodium hydroxide gives 1-(1H-benzo[d]imidazole-2-ylthio)-3- chloropropan-2-ol (3), which upon refluxing with different substituted aliphatic and aromatic amines in methanol produces novel benzimidazole derivatives (4a-l). These compounds were characterized by their melting point, FT-IR, 1H NMR and Mass spectral data. The synthesized molecules screened for antibacterial and antifungal activity. The compound 4l exhibited excellent activity at MIC 0.4 μg/mL against C. albicans. Compounds 4c and 4e showed MIC at 3.12 μg/mL against E. coli and the compounds 4l and 4J exhibited MIC at 3.12 μg/mL against S. aureus. Docking studies and activity result reveals the novel benzimidazole compound 4l has excellent antifungal and antibacterial effect.

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