Syntheses and biological evaluation of 2-amino-3-acyl-tetrahydrobenzothiophene derivatives; antibacterial agents with antivirulence activity

Synthesis of some new bis(chalcones)-based thienothiophene derivatives and study of their synthetic utilities as building blocks for new bis(thiazole), bis(dihydropyran), bis(dihydro pyridine), bis(isoxazoles), bis(pyrazoles), bis(hydropyrimidinethiones), bis(tetrahydro diazepines, oxazepines) and bis(dihydrobenzodiazepnies, benzoxazepines) each linked to a thienothiophene core, is reported. Biological evaluation of the obtained compounds as antibacterial agents was achieved. Compounds 4b, 4c, 7a, 6a, 9a and 11b were found to be very potent against P. aeruginosa, E. coli and K. pneumonia.

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Synthesis, Characterization and Biological Evaluation of Some 2-[1-(1,3-Diphenyl-1HPyrazol-4-yl)-meth-(E)-ylidene]indan-1-one Derivatives as Antibacterial Agents

Asian Journal of Organic & Medicinal Chemistry ◽

10.14233/ajomc.2020.ajomc-p258 ◽

2020 ◽

Vol 5 (2) ◽

pp. 127-132

Author(s):

Uttam B. Chougule ◽

Hemant V. Chavan ◽

Savita R. Dhongade

Keyword(s):

Reaction Time ◽

Antibacterial Agents ◽

Spectroscopic Analysis ◽

Knoevenagel Condensation ◽

Biological Evaluation ◽

Bacterial Strains ◽

Short Reaction Time ◽

E Coli ◽

Time Structures ◽

Substituted 1

A new series of 2-[1-(1,3-diphenyl-1H-pyrazol-4-yl)-meth-(E)-ylidene]-indan-1-one derivatives (5a-l) have been synthesized through through the Knoevenagel condensation of pyrazole carbaldehydes with differently substituted 1-indanone derivatives in the presence of base. A high yielding and solvent-free method was developed for the synthesis of hydrazones from acetophenones under microwave irradiation in a very short reaction time. Structures of the newly synthesized compounds were affirmed by IR, 1H & 13C NMR and mass spectroscopic analysis. The confirmed structures were screened for their antibacterial potency against S. aureus and E. coli bacterial strains. Among the series, compounds 5b, 5c and 5f were evoked as potent antibacterial agents

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Design, synthesis and evaluation of anti-inflammatory, analgesic and antibacterial activity of 2, 4, 6-trisubstituted quinazoline derivatives

Ovidius University Annals of Chemistry ◽

10.2478/auoc-2018-0014 ◽

2018 ◽

Vol 29 (2) ◽

pp. 97-102

Author(s):

Nivrati Jain ◽

Harshita Jain ◽

Ashish Jain ◽

Veerasamy Ravichandran ◽

Prateek Jain

Keyword(s):

Antibacterial Activity ◽

Antibacterial Agents ◽

Biological Evaluation ◽

Spectroscopy Analysis ◽

Design Synthesis ◽

E Coli ◽

Quinazoline Derivatives ◽

Anti Inflammatory ◽

Synthesis And Biological Evaluation ◽

Mass Spectroscopy Analysis

Abstract We described here the synthesis and biological evaluation of a series of 2, 4, 6-trisubstituted quinazoline derivatives as potential anti-inflammatory, analgesic and antibacterial agents. The synthesized compounds were characterized by FTIR, 1H NMR and mass spectroscopy analysis. We found that the compounds 6b, 6e, 6g, 6h and 6j showed better anti-inflammatory activity than indomethacin. Compounds 6b, 6e, 6h, 6j and 6l were found to exhibit appreciable analgesic activity, and 6b, 6g and 6k showed good antibacterial activity against Gram (+) bacteria: B. subtilis, S. aureus, S. epidermis, and Gram (-) bacteria: E. coli, P. aeruginosa and K. pneumoniae. Compound 6b showed overall better anti-inflammatory, analgesic and antibacterial activity among the synthesized compounds. The results of the present study could be helpful for the designing of effective anti-inflammatory, analgesic and antibacterial agents.

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Synthesis, Antibacterial, and Antioxidant Evaluation of Novel Series of Condensed Thiazoloquinazoline with Pyrido, Pyrano, and Benzol Moieties as Five- and Six-Membered Heterocycle Derivatives

Molecules ◽

10.3390/molecules26020357 ◽

2021 ◽

Vol 26 (2) ◽

pp. 357

Author(s):

Ebraheem Abdu Musad Saleh ◽

Abdullah Mohammed AL Dawsari ◽

Kakul Husain ◽

Ismail Hassan Kutty ◽

K.M.Lokanatha Rai

Keyword(s):

Antibacterial Activity ◽

Heterocyclic Compounds ◽

Antibacterial Agents ◽

Biological Evaluation ◽

Bacterial Strains ◽

E Coli ◽

Antioxidant Evaluation ◽

Synthetic Approaches ◽

Membered Heterocycle ◽

Molecular Framework

A novel synthesis of thiazolo[2,3-b]quinazolines 4(a–e), pyrido[2′,3′:4,5]thiazolo[2,3-b]quinazolines {5(a–e), 6(a–e), and 7(a–e)}, pyrano[2′,3′:4,5]thiazolo[2,3-b]quinazolines 8(a–e), and benzo[4,5]thiazolo[2,3-b]quinazoloine9(a–e) derivatives starting from 2-(Bis-methylsulfanyl-methylene)-5,5-dimethyl-cyclohexane-1,3-dione 2 as efficient α,α dioxoketen dithioacetal is reported and the synthetic approaches of these types of compounds will provide an innovative molecular framework to the designing of new active heterocyclic compounds. In our study, we also present optimization of the synthetic method along with a biological evaluation of these newly synthesized compounds as antioxidants and antibacterial agents against the bacterial strains, like S. aureus, E. coli, and P. aeruginosa. Among all the evaluated compounds, it was found that some showed significant antioxidant activity at 10 μg/mL while the others exhibited better antibacterial activity at 100 μg/mL. The results of this study showed that compound 6(c) possessed remarkable antibacterial activity, whereas compound 9(c) exhibited the highest efficacy as an antioxidant. The structures of the new synthetic compounds were elucidated by elemental analysis, IR, 1H-NMR, and 13C-NMR.

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SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF 3-FORMYL INDOLE BASED SCHIFF BASES

Journal of Biomedical and Pharmaceutical Research ◽

10.32553/jbpr.v7i6.561 ◽

2018 ◽

Vol 7 (6) ◽

Author(s):

Singh Gurvinder ◽

Singh Prabhsimran ◽

Dhawan R. K.

Keyword(s):

Antimicrobial Activity ◽

Spectral Analysis ◽

Schiff Bases ◽

Antimicrobial Agents ◽

Biological Evaluation ◽

Fungal Strain ◽

Bacterial Strains ◽

Standard Drug ◽

Gram Negative ◽

E Coli

In order to develop new antimicrobial agents, a series of 3-formyl indole based Schiff bases were synthesized by reacting 3-formyl indole(indole-3-carboxaldehyde) with substituted aniline taking ethanol as solvent. The reaction was carried in the presence of small amount of p-toluene sulphonic acid as catalyst.All the synthesized compounds were characterized by IR, 1H-NMR spectral analysis. All the synthesized compounds were evaluated for antimicrobial activity against two gram positive bacterial strains (B. subtilisand S. aureus) and two gram negative bacterial strains (P. aeruginosaand E. coli) and one fungal strain (C. albicans). All the synthesized compounds were found to have moderate to good antimicrobial activity. The standard drug amoxicillin, fluconazole were used for antimicrobial activity. Among the synthesized compounds, the maximum antimicrobial activity was shown by compounds GS04, GS07, GS08 and GS10.

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Large-scale High-throughput Screening Revealed 5'-(carbonylamino)-2,3'- bithiophene-4'-carboxylate as Novel Template for Antibacterial Agents

Current Drug Discovery Technologies ◽

10.2174/1570163816666190603095521 ◽

2020 ◽

Vol 17 (5) ◽

pp. 716-724

Author(s):

Yan A. Ivanenkov ◽

Renat S. Yamidanov ◽

Ilya A. Osterman ◽

Petr V. Sergiev ◽

Vladimir A. Aladinskiy ◽

...

Keyword(s):

Antibacterial Activity ◽

High Throughput ◽

High Throughput Screening ◽

Large Scale ◽

Antibacterial Agents ◽

Sos Response ◽

Luciferase Assay ◽

Translational Machinery ◽

E Coli ◽

New Class

Background: The key issue in the development of novel antimicrobials is a rapid expansion of new bacterial strains resistant to current antibiotics. Indeed, World Health Organization has reported that bacteria commonly causing infections in hospitals and in the community, e.g. E. Coli, K. pneumoniae and S. aureus, have high resistance vs the last generations of cephalosporins, carbapenems and fluoroquinolones. During the past decades, only few successful efforts to develop and launch new antibacterial medications have been performed. This study aims to identify new class of antibacterial agents using novel high-throughput screening technique. Methods: We have designed library containing 125K compounds not similar in structure (Tanimoto coeff.< 0.7) to that published previously as antibiotics. The HTS platform based on double reporter system pDualrep2 was used to distinguish between molecules able to block translational machinery or induce SOS-response in a model E. coli system. MICs for most active chemicals in LB and M9 medium were determined using broth microdilution assay. Results: In an attempt to discover novel classes of antibacterials, we performed HTS of a large-scale small molecule library using our unique screening platform. This approach permitted us to quickly and robustly evaluate a lot of compounds as well as to determine the mechanism of action in the case of compounds being either translational machinery inhibitors or DNA-damaging agents/replication blockers. HTS has resulted in several new structural classes of molecules exhibiting an attractive antibacterial activity. Herein, we report as promising antibacterials. Two most active compounds from this series showed MIC value of 1.2 (5) and 1.8 μg/mL (6) and good selectivity index. Compound 6 caused RFP induction and low SOS response. In vitro luciferase assay has revealed that it is able to slightly inhibit protein biosynthesis. Compound 5 was tested on several archival strains and exhibited slight activity against gram-negative bacteria and outstanding activity against S. aureus. The key structural requirements for antibacterial potency were also explored. We found, that the unsubstituted carboxylic group is crucial for antibacterial activity as well as the presence of bulky hydrophobic substituents at phenyl fragment. Conclusion: The obtained results provide a solid background for further characterization of the 5'- (carbonylamino)-2,3'-bithiophene-4'-carboxylate derivatives discussed herein as new class of antibacterials and their optimization campaign.

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Synthesis and Biological Evaluation of a New Series of Benzothiazole-Quinolone Hybrids as Antibacterial Agents

Letters in Drug Design & Discovery ◽

10.2174/157018008784912072 ◽

2008 ◽

Vol 5 (5) ◽

pp. 353-357 ◽

Cited By ~ 1

Author(s):

Ahmed Kamal ◽

S. Ahmed ◽

M. A. Khan ◽

Rajesh Shetty ◽

B. Siddhardha ◽

...

Keyword(s):

Antibacterial Agents ◽

Biological Evaluation ◽

Synthesis And Biological Evaluation

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Apomorphine Targets the Pleiotropic Bacterial Regulator Hfq

Antibiotics ◽

10.3390/antibiotics10030257 ◽

2021 ◽

Vol 10 (3) ◽

pp. 257

Author(s):

Florian Turbant ◽

David Partouche ◽

Omar El Hamoui ◽

Sylvain Trépout ◽

Théa Legoubey ◽

...

Keyword(s):

Small Rnas ◽

Antibacterial Agents ◽

Amyloid Fibrils ◽

Noncoding Rnas ◽

Amyloid Formation ◽

Gram Negative Bacteria ◽

Translation Efficiency ◽

Gram Negative ◽

Bacterial Adaptation ◽

E Coli

Hfq is a bacterial regulator with key roles in gene expression. The protein notably regulates translation efficiency and RNA decay in Gram-negative bacteria, thanks to its binding to small regulatory noncoding RNAs. This property is of primary importance for bacterial adaptation and survival in hosts. Small RNAs and Hfq are, for instance, involved in the response to antibiotics. Previous work has shown that the E. coli Hfq C-terminal region (Hfq-CTR) self-assembles into an amyloid structure. It was also demonstrated that the green tea compound EpiGallo Catechin Gallate (EGCG) binds to Hfq-CTR amyloid fibrils and remodels them into nonamyloid structures. Thus, compounds that target the amyloid region of Hfq may be used as antibacterial agents. Here, we show that another compound that inhibits amyloid formation, apomorphine, may also serve as a new antibacterial. Our results provide an alternative in order to repurpose apomorphine, commonly used in the treatment of Parkinson’s disease, as an antibiotic to block bacterial adaptation to treat infections.

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Synthesis and Biological Evaluation of Fingolimod Derivatives as Antibacterial Agents

ACS Omega ◽

10.1021/acsomega.1c02591 ◽

2021 ◽

Author(s):

Matej Zore ◽

Shella Gilbert-Girard ◽

Inés Reigada ◽

Jayendra Z. Patel ◽

Kirsi Savijoki ◽

...

Keyword(s):

Antibacterial Agents ◽

Biological Evaluation ◽

Synthesis And Biological Evaluation

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Design, Synthesis and Biological Evaluation of Novel Benzothiazole Based [1,2,4]Triazolo[4,3-c]quinazoline Derivatives

Asian Journal of Chemistry ◽

10.14233/ajchem.2020.22453 ◽

2020 ◽

Vol 32 (3) ◽

pp. 580-586

Author(s):

Ranjit V. Gadhave ◽

Bhanudas S. Kuchekar

Keyword(s):

Biological Evaluation ◽

Bacterial Strains ◽

Active Compounds ◽

Design Synthesis ◽

Structural Modifications ◽

E Coli ◽

Chemical Structures ◽

Ft Ir ◽

Antioxidant Agent

A new series of N-(benzo[d]thiazol-2-yl)-[1,2,4]triazolo[4,3-c]quinazoline-5-carboxamide derivatives were synthesized by condensation of [1,2,4]triazolo[4,3-c]quinazoline-5-carboxylate derivatives with substituted benzothiazoles. The chemical structures of the synthesized compounds were confirmed by FT-IR, MS and 1H NMR spectra. Designed triazoloquinazoline derivatives were docked with oxido-reductase enzyme (PDB Code 4h1j) and DNA gyrase enzyme (PDB Code 3g75). Based on high binding affinity score, the best compound were selected for synthesis and subjected to in vitro antioxidant and antibacterial activity. Compounds 7a and 7d were found to be most active compounds as antioxidant agent among this series when compared with ascorbic acid. Compounds 7a, 7d and 7f were found to be most active compounds as an antibacterial agents among this series when compared with ciprofloxacin against bacterial strains such as S. aureus (ATCC 25923), E. coli (ATCC 25922) and P. aeruginosa (ATCC 27853). Study revealed that the most active compounds after structural modifications can be exploited as lead molecules for other pharmacological activities such as anti-inflammatory, anticancer and antidepressant activities.

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