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Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines.

ABSTRACT: Thiazole derivatives attract the attention of scientists both in the field of organic synthesis and bioactivity research due to their high biological activity. In the present study, thiazole ring was obtained by the interaction of 1-(4-(bromoacetyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid with thiocarbamide or benzenecarbothioamide, as well as tioureido acid. A series of substituted 1-(3-(1,3-thiazol-2-yl)phenyl)-5-oxopyrrolidines with pyrrolidinone, thiazole, pyrrole, 1,2,4-triazole, oxadiazole and benzimidazole heterocyclic fragments were synthesized and their antibacterial properties were evaluated against Gram-positive strains of Staphylococcus aureus, Bacillus cereus, Listeria monocytogenes and Gram-negative Pseudomonas aeruginosa, Escherichia coli and Salmonella enterica enteritidis. The vast majority of compounds exhibited between twofold and 16-fold increased antibacterial effect against the test-cultures when compared with Oxytetracycline.

SUBMITTER: Sapijanskaite-Banevic B

PROVIDER: S-EPMC7288019 | biostudies-literature | 2020 May

REPOSITORIES: biostudies-literature

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Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines.

Sapijanskaitė-Banevič Birutė B Šovkovaja Božena B Vaickelionienė Rita R Šiugždaitė Jūratė J Mickevičiūtė Eglė E

Molecules (Basel, Switzerland) 20200522 10

Thiazole derivatives attract the attention of scientists both in the field of organic synthesis and bioactivity research due to their high biological activity. In the present study, thiazole ring was obtained by the interaction of 1-(4-(bromoacetyl)phenyl)-5-oxopyrrolidine-3-carboxylic acid with thiocarbamide or benzenecarbothioamide, as well as tioureido acid. A series of substituted 1-(3-(1,3-thiazol-2-yl)phenyl)-5-oxopyrrolidines with pyrrolidinone, thiazole, pyrrole, 1,2,4-triazole, oxadiazo ...[more]

PMID: 32456041

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Project description:BACKGROUND:There 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. RESULTS:The 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. CONCLUSIONS:The 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.

Dataset Information

Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines.

Publications

Synthesis, Characterization and Bioassay of Novel Substituted 1-(3-(1,3-Thiazol-2-yl)phenyl)-5-oxopyrrolidines.

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