Benzofuran-oxadiazole hybrids: Design, Synthesis and antimicrobial activity studies

The six benzofuran-oxadiazole derivatives (4a-d) and (5a-b) have been designed, synthesized, characterized and evaluated for antimicrobial activity. The key synthetic intermediate 5-bromo-N'-hydroxybenzofuran -2-carboxamidine (3) was prepared from 5-bromobenzofuran-2-carboxylic acid (1) in two consecutive steps involving reaction with NaN3, in presence of TEA, Xtalfluor-E, PPh3 in dry DCM at 0oC followed by the treatment of resulting carbonitrile (2) with hydroxylamine hydrochloride in presence of sodium methoxide under reflux in aqueous ethanol. Reaction of carboxamidine (3) with different aryl esters in presence of K2CO3 under reflux conditions in toluene afforded 3-(5-bromobenzofuran-2-yl)-5-substituted phenyl-1,2,4-oxadiazoles (4a-d) while the refluxion of a solution of carboxamidine (3) in dichloromethane with chloro/bromo acetyl chloride in presence of TEA and a catalytic amount of HBTU furnished 3-(5-bromobenzofuran-2-yl)-5-(chloromethyl)-1,2,4-oxadia zole (5a) and 3-(5-bromobenzofuran-2-yl)-5-(bromomethyl)-1,2,4-oxadiazole (5b).

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Design, Synthesis and In Vitro Antimicrobial Activity of 6-(1H-Benzimidazol-2-yl)-3,5-dimethyl-4-oxo-2-thio-3,4-dihydrothieno[2,3-d]pyrimidines

Scientia Pharmaceutica ◽

10.3390/scipharm89040049 ◽

2021 ◽

Vol 89 (4) ◽

pp. 49

Author(s):

Sergiy V. Vlasov ◽

Olena D. Vlasova ◽

Hanna I. Severina ◽

Konstantin Y. Krolenko ◽

Oleksandr V. Borysov ◽

...

Keyword(s):

Antimicrobial Activity ◽

Carboxylic Acid ◽

Bacterial Resistance ◽

Rapid Development ◽

Antimicrobial Properties ◽

Docking Studies ◽

Antibacterial Drug ◽

Design Synthesis ◽

Drug Candidates

The rapid development in bacterial resistance to many groups of known antibiotics forces the researchers to discover antibacterial drug candidates with previously unknown mechanisms of action, one of the most relevant being the inhibition of tRNA (Guanine37-N1)-methyltransferase (TrmD). The discovery of selective TrmD inhibitors in the series of carboxamide derivatives of thienopyrimidines became a background for further modification of the similar structures aimed at the development of promising antibacterial agents. As part of this research, we carried out the construction of heterocyclic hybrids bearing the moieties of thieno[2,3-d]pyrimidine and benzimidazole starting from 3,5-dimethyl-4-oxo-2-thioxo-1H-thieno[2,3-d]pyrimidine-6-carboxylic acid, which was used as the pivotal intermediate. The hybrid molecule of 6-(1H-benzimidazol-2-yl)-3,5-dimethyl-2-thioxo-1H-thieno[2,3-d]pyrimidin-4-one prepared via condensation of the carboxylic acid with ortho-phenylenediamine was further alkylated with aryl/hetaryl chloroacetamides and benzyl chloride to produce the series of S-alkyl derivatives. The results of molecular docking studies for the obtained series of S-alkyl benzimidazole-thienopyrimidines showed their high affinity to the TrmD isolated from the P. aeruginosa. The results of antimicrobial activity screening revealed the antimicrobial properties for all of the studied molecules against both Gram-positive and Gram-negative bacteria and the Candida albicans fungal strain. The highest antimicrobial activity was determined for 2-{[6-(1H-benzimidazol-2-yl)-3,5-dimethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl]thio}-N-(4-isopropylphenyl)acetamide, which also had the highest affinity to the TrmD inhibitor’s binding site according to the docking studies results.

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SYNTHESIS AND CHARACTERIZATION OF SOME ISOXAZOLE DERIVATIVES FOR ANTIMICROBIAL ACTIVITY

INDIAN DRUGS ◽

10.53879/id.55.08.11119 ◽

2018 ◽

Vol 55 (08) ◽

pp. 18-24

Author(s):

Umakant ◽

◽

D. Sharma ◽

D. Pathak ◽

G. Sharma ◽

...

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Antifungal Activity ◽

Future Development ◽

Hydroxylamine Hydrochloride ◽

Catalytic Amount ◽

Synthesis And Characterization ◽

Good Antibacterial Activity ◽

Isoxazole Derivatives

In the present work, some newer 3,5-substituted diphenyl isoxazole derivatives (compounds 1-10) were synthesised by reaction of hydroxylamine hydrochloride with various freshly synthesised 1-(substituted phenyl)-3-(substituted phenyl)prop-2en-1-one derivatives (compounds. 1A-10A) in the presence of pyridine and catalytic amount of sodium hydroxide. Compounds 2, 4, 5, 10 were found to possess good antibacterial activity and compounds 3 and 10 showed good antifungal activity when compared with standard drugs ciprofloxacin and fluconazole at the concentration 50 μg mL-1. These results suggest that the synthesized isoxazole derivatives exhibit promising activity and this work may pave the way for future development of promising compounds for this purpose.

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INSILICO DESIGN, SYNTHESIS AND SCREENING OF NOVEL 1, 3, 4-OXADIAZOLE DERIVATIVES FOR ANALGESIC, ANTI-INFLAMMATORY AND ANTIMICROBIAL ACTIVITY

International Journal of Biomedical Research ◽

10.7439/ijbr.v1i3.63 ◽

2011 ◽

Vol 1 (3) ◽

Author(s):

Biju C.R ◽

Manju Prathap ◽

Byju K ◽

Rekha K.

Keyword(s):

Antimicrobial Activity ◽

Design Synthesis ◽

Oxadiazole Derivatives ◽

Anti Inflammatory

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Design, synthesis and antimicrobial activity of new biquinoline derivatives

Journal of the Serbian Chemical Society ◽

10.2298/jsc110630197s ◽

2012 ◽

Vol 77 (3) ◽

pp. 279-286 ◽

Cited By ~ 10

Author(s):

Nirav Shah ◽

Nimesh Shah ◽

Manish Patel ◽

Ranjan Patel

Keyword(s):

Antimicrobial Activity ◽

Antifungal Activity ◽

Efficient Method ◽

Ethyl Cyanoacetate ◽

Catalytic Amount ◽

Antibacterial And Antifungal Activity ◽

Design Synthesis ◽

Antibacterial And Antifungal

A simple and efficient method has been developed for the synthesis of some novel biquinoline derivatives bearing a thiazole moiety through a onepot three-component condensation of 2-chlro-3-formylquinolines, ethyl cyanoacetate and ?-enaminone using catalytic amount of piperidine in refluxing ethanol. These molecules were evaluated in vitro for their antibacterial and antifungal activity. Most of the compounds exhibited moderate antibacterial and antifungal activity against all the tested strains.

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Design, Synthesis and Docking Studies of Some Novel Fluoroquinolone Compounds with Antibacterial Activity

Revista de Chimie ◽

10.37358/rc.18.4.6207 ◽

2018 ◽

Vol 69 (4) ◽

pp. 815-822 ◽

Cited By ~ 1

Author(s):

Lucia Pintilie ◽

Amalia Stefaniu ◽

Alina Ioana Nicu ◽

Maria Maganu ◽

Miron Teodor Caproiu

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Molecular Docking ◽

Drug Discovery ◽

Elemental Analysis ◽

Docking Studies ◽

Receptor Protein ◽

Chemical Methods ◽

Design Synthesis ◽

Gram Negative

A new series of fluoroquinolone compounds have been obtained by Gould-Jacobs method. The compounds have been characterized by physic-chemical methods (elemental analysis, FTIR, NMR, UV-Vis) and by antimicrobial activity against Gram-positive and Gram-negative microorganisms. For the synthesized compounds have been performed calculations of characteristics and molecular properties, using Spartan�14 Software from Wavefunction, Inc. Irvine, CA. and molecular docking studies using CLC Drug Discovery Workbench 2.4 software, to identify and visualize the most likely interaction ligand (fluoroquinolone) with the receptor protein.

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Design, Synthesis and Biological Evaluation of Some Oxadiazole Derivatives as Novel Amide-Based Inhibitors of Soluble Epoxide Hydrolase

Letters in Drug Design & Discovery ◽

10.2174/1570180811666140220005530 ◽

2014 ◽

Vol 11 (6) ◽

pp. 721-730 ◽

Cited By ~ 8

Author(s):

Elham Zavareh ◽

Mahdi Hedayati ◽

Laleh Rad ◽

Azin Kiani ◽

Soraya Shahhosseini ◽

...

Keyword(s):

Epoxide Hydrolase ◽

Soluble Epoxide Hydrolase ◽

Biological Evaluation ◽

Design Synthesis ◽

Oxadiazole Derivatives ◽

Synthesis And Biological Evaluation

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Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

Applied Sciences ◽

10.3390/app11031180 ◽

2021 ◽

Vol 11 (3) ◽

pp. 1180

Author(s):

Kinga Paruch ◽

Łukasz Popiołek ◽

Anna Biernasiuk ◽

Anna Berecka-Rycerz ◽

Anna Malm ◽

...

Keyword(s):

Antimicrobial Activity ◽

Carboxylic Acid ◽

Bacterial Infections ◽

Acid Hydrazide ◽

Antimicrobial Effect ◽

In Vitro Antimicrobial Activity ◽

Research Goal ◽

New Compounds ◽

Derivatives Of

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

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Sulfaguanidine Hybrid with Some New Pyridine-2-One Derivatives: Design, Synthesis, and Antimicrobial Activity against Multidrug-Resistant Bacteria as Dual DNA Gyrase and DHFR Inhibitors

Antibiotics ◽

10.3390/antibiotics10020162 ◽

2021 ◽

Vol 10 (2) ◽

pp. 162

Author(s):

Ahmed Ragab ◽

Sawsan A. Fouad ◽

Ola A. Abu Ali ◽

Entsar M. Ahmed ◽

Abeer M. Ali ◽

...

Keyword(s):

Antimicrobial Activity ◽

Fungal Growth ◽

Dna Gyrase ◽

Multidrug Resistant ◽

Resistant Bacteria ◽

Design Synthesis ◽

Potent Inhibition ◽

Ic50 Values ◽

Dhfr Inhibitors ◽

Positive Controls

Herein, a series of novel hybrid sulfaguanidine moieties, bearing 2-cyanoacrylamide 2a–d, pyridine-2-one 3–10, and 2-imino-2H-chromene-3-carboxamide 11, 12 derivatives, were synthesized, and their structure confirmed by spectral data and elemental analysis. All the synthesized compounds showed moderate to good antimicrobial activity against eight pathogens. The most promising six derivatives, 2a, 2b, 2d, 3a, 8, and 11, revealed to be best in inhibiting bacterial and fungal growth, thus showing bactericidal and fungicidal activity. These derivatives exhibited moderate to potent inhibition against DNA gyrase and DHFR enzymes, with three derivatives 2d, 3a, and 2a demonstrating inhibition of DNA gyrase, with IC50 values of 18.17–23.87 µM, and of DHFR, with IC50 values of 4.33–5.54 µM; their potency is near to that of the positive controls. Further, the six derivatives exhibited immunomodulatory potential and three derivatives, 2d, 8, and 11, were selected for further study and displayed an increase in spleen and thymus weight and enhanced the activation of CD4+ and CD8+ T lymphocytes. Finally, molecular docking and some AMED studies were performed.

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7-Alkoxy-appended coumarin derivatives: synthesis, photo-physical properties, aggregation behaviours and current–voltage (I–V) characteristic studies on thin films

RSC Advances ◽

10.1039/d1ra00762a ◽

2021 ◽

Vol 11 (17) ◽

pp. 10212-10223

Author(s):

Abhijit Rudra Paul ◽

Bapi Dey ◽

Sudip Suklabaidya ◽

Syed Arshad Hussain ◽

Swapan Majumdar

Keyword(s):

Thin Films ◽

Carboxylic Acid ◽

Physical Properties ◽

Chemical Characteristics ◽

Coumarin Derivatives ◽

Design Synthesis ◽

Electrical Switching ◽

Physico Chemical ◽

Current Voltage

In this article, we demonstrate the design, synthesis and physico-chemical characteristics, including electrical switching behaviours of long alkoxy-appended coumarin carboxylate/carboxylic acid in thin films.

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