Synthesis, antimicrobial, cytotoxic and E. coli DNA gyrase inhibitory activities of coumarinyl amino alcohols

Priyanka, .; Singh, Vineeta; Ekta, .; Katiyar, Diksha

doi:10.1016/j.bioorg.2017.01.019

Cited by 22 publications

(7 citation statements)

References 23 publications

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“…The values of zone of inhibition for bacterial are revealed in Table 1 . The minimum inhibitory concentration (MIC, μg/mL) is the lowest concentration of a chemical that prevents visible growth of bacterium in microgram per milliliter of active compounds (Table 1 ) was determined by the microorganism’s susceptibility tests in nutrient and potato dextrose broths were used for the determination of MIC [ 27 ]. The results revealed that seven organic compounds displayed better inhibitory effects on the growth of the tested bacterial strains.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, anti-microbial activity, cytotoxicity of some novel substituted (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs

Shankar

Pochampally

Balabadra

et al. 2018

Chemistry Central Journal

132

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BackgroundThere is a dire need for the discovery and development of new antimicrobial agents after several experiments for a better resistance of microorganisms towards antimicrobial agents become a serious health problem for a few years in the past. As benzimidazole possess various types of biological activities, it has been synthesized, in the present study, a new series of (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs by using the condensation and screened for its in vitro antimicrobial activity and cytotoxicity.ResultsThe synthesized (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl) benzofuran-2-yl)(phenyl)methanone analogs were confirmed by IR, 1H and 13C-NMR, MS spectra and HRMS spectral data. The synthesized compounds were evaluated for their in vitro antimicrobial potential against Gram-positive (Bacillus subtilis, Bacillus megaterium, Staph aureus and Streptococcus pyogenes), Gram-negative (Escherichia coli, Proteus vulgaris, Proteus mirabilis and Enterobacter aerogenes) bacterial and fungal (Aspergillus niger, Candida albicans, Fusarium oxysporum, Fusarium solani) strains by disc diffusion method and the minimum inhibitory concentration (MIC) in which it has been recorded in microgram per milliliter in comparison to the reference drugs, ciprofloxacin (antibacterial) and nystatin (antifungal). Further, the cytotoxicity (IC50 value) has also been assessed on human cervical (HeLa), Supt1 cancer cell lines by using MTT assay.ConclusionsThe following screened compounds (4d), (4f), (4g), (4k), (4l), (4o) and (4u) were found to be the best active against all the tested bacterial and fungal strains among all the demonstrated compounds of biological study. The MIC determination was also carried out against bacteria and fungi, the compounds (4f) and (4u) are found to be exhibited excellent potent against bacteria and fungi respectively. The compounds (4f) and (4u) were shown non-toxic in nature after screened for cytotoxicity against the cancer cell lines of human cervical (HeLa) and Supt1. Additionally, structure and antibacterial activity relationship were also further supported by in silico molecular docking studies of the active compounds against DNA topoisomerase. Electronic supplementary materialThe online version of this article (10.1186/s13065-017-0364-3) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Synthesis, anti-microbial activity, cytotoxicity of some novel substituted (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs

Shankar

Pochampally

Balabadra

et al. 2018

Chemistry Central Journal

132

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“…The isocnidilide compound was selected for the docking study based on the higher percentage contents. The structures of antibacterial target protein DNA gyrase, PDB: 1KZN [ 48 ], antioxidant tyrosinase enzyme, PDB ID: 3NM8 [ 49 ], and anti-inflammatory target protein cyclooxygenase-2, PDB ID: 1CX2 [ 50 ] enzymes were revealed from the protein data bank.…”

Section: Methodsmentioning

confidence: 99%

Determination of Chemical Composition, In Vitro and In Silico Evaluation of Essential Oil from Leaves of Apium graveolens Grown in Saudi Arabia

et al. 2021

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The aim of this study was to explore the composition and evaluate the in silico and in vitro antioxidants and antimicrobial and anti-inflammatory effects of Apium graveolens var. dulce leaves essential oil (AGO) collected from Al-Kharj (Saudi Arabia). AGO was isolated using the hydro-distillation method, and its composition was studied using gas-chromatography-mass Spectrometry (GC–MS), antimicrobial activities using well diffusion assay, and antioxidant and anti-inflammatory activities using spectrophotometric methods. The pharmacological activities of their major compounds were predicted using PASS (prediction of activity spectra for substances) and drug-likening properties by ADME (absorption, distribution, metabolism, and excretion) through web-based online tools. Isocnidilide (40.1%) was identified as the major constituent of AGO along with β-Selinene, Senkyunolide A, Phytyl acetate, and 3-Butylphthalide. AGO exhibited a superior antibacterial activity, and the strongest activity was detected against Gram-positive bacteria and Candida albicans. Additionally, it exhibited a weaker antioxidant potential and stronger anti-inflammatory effects. PASS prediction supported the pharmacological finding, whereas ADMET revealed the safety of AGO. The molecular docking of isocnidilide was carried out for antibacterial (DNA gyrase), antioxidant (tyrosinase), and anti-inflammatory (cyclooxygenase-2) activities. The docking simulation results were involved hydrophilic interactions and demonstrated high binding affinity of isocnidilide for anti-inflammatory protein (cycloxygenase-2). The presence of isocnidilide makes AGO a potential anti-inflammatory and antimicrobial agent. AGO, and its major metabolite isocnidilide, may be a suitable candidate for the future drug development.

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“…In derivatives Id-f and IIa-f the ethanolamine side chain was modified to 1-amino-2-propanol, which is an important feature in diverse antimicrobial agents. [13][14][15][16] Moreover, this β-aminoalcohol motif has been linked with antimycobacterial action. Ethambutol 17 is the main representative of this category of antitubercular agents.…”

Section: A Rt I C L E I N F O Abstractmentioning

confidence: 99%

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

Georgiadis

Kourbeli

Ioannidou

et al. 2019

Bioorganic & Medicinal Chemistry Letters

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Synthesis, antimicrobial, cytotoxic and E. coli DNA gyrase inhibitory activities of coumarinyl amino alcohols

Cited by 22 publications

References 23 publications

Synthesis, anti-microbial activity, cytotoxicity of some novel substituted (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs

Synthesis, anti-microbial activity, cytotoxicity of some novel substituted (5-(3-(1H-benzo[d]imidazol-2-yl)-4-hydroxybenzyl)benzofuran-2-yl)(phenyl)methanone analogs

Determination of Chemical Composition, In Vitro and In Silico Evaluation of Essential Oil from Leaves of Apium graveolens Grown in Saudi Arabia

Synthesis of diphenoxyadamantane alkylamines with pharmacological interest

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