Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones

Desai, N. C.; Vaghani, H. V.; Patel, Bonny Y.; Karkar, Tushar J.

doi:10.4172/pharmaceutical-sciences.1000351

Cited by 24 publications

(7 citation statements)

References 37 publications

(38 reference statements)

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“…This revealed the influence of electron-withdrawing functional groups on antimicrobial activity. This type of compound with an electron-withdrawing group has been reported to have excellent antimicrobial activity [ 57 ]. Against P. aeruginosa , Q8 having chlorine as its substituent, showed excellent activity higher than the reference standards while Q7 has the same MIC value of 0.2 µg/mL as ciprofloxacin.…”

Section: Resultsmentioning

confidence: 99%

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

et al. 2021

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A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1–Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes′ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.

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Section: Resultsmentioning

confidence: 99%

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

et al. 2021

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“…Pyridine heterocycle was confirmed through C N stretching at 1609 cm À1 . 1 H NMR signal presented at 7.00 ppm confirmed the presence of C H (arylidene proton). Furthermore, the signal that appeared at 1.85 ppm confirmed three protons presented in the methyl group of the thiazolidinone core structure.…”

Section: Introductionmentioning

confidence: 82%

“…To adequately handle the spread of antimicrobial resistance, the search for the advancement of novel antimicrobial agents is the only way to resolve the problem. Heterocyclic compounds have drawn the attention of scientific experts and pharmacologists in light of their biological significance [1,2]. It has been observed that hybrids of bioactive pharmacophores (pyridine, coumarin, and 4-thiazolidinone) in the current medications create a significant effect on the pharmaceutical profile [3][4][5][6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Desai

Mehta

Jethawa

et al. 2022

Journal of Heterocyclic Chem

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Antimicrobial resistance is a major threat to mankind. Many frontline medications are ineffective against antimicrobial-resistant strains which are also responsible for the high mortality rate worldwide. The urgency to create new sets of antimicrobial agents is a priority in present circumstances. In continuation to this, we have strategically designed and synthesized some novel hybrids of 4-thiazolidinone bearing coumarin and pyridine cores for the evaluation of antimicrobial efficacy. A three-step multicomponent reaction was performed via imine formation, cyclization, and Knoevenagel condensation for the synthesis of titled compounds (5a-o). The synthesized entities were characterized through different analytical techniques, that is, IR, 1 H NMR, 13 C NMR, and mass spectra. On evaluating the potency of our synthesized hybrids, we received some promising results. Compound 5m was identified as the most potent component possessing 50 μg/ml (minimum inhibitory concentration [MIC] value) against S. aureus and 250 μg/ml (MIC value) against C. albicans strains. Further, a molecular docking study against microbial DNA gyrase was carried out to understand the binding profile of synthesized molecules, which supported their in-vitro antimicrobial activity. These data helped to gain an insight into their plausible mechanism of action. Their binding affinity scores correlated well with the in-vitro antimicrobial activities while their binding modes proposed the involvement of steric, electrostatic, and hydrogen-bonding interactions with the active site.

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“…Thioxoimidazolidin-4-one derivatives prevent the α-amylase and α-glucosidase enzymes activities and used for the treatment of diabetes-related diseases 7 . Moxonidine is a new generation antihypertensive drug containing imidazole moiety 8 . Tipifarnib is an imidazole derivative which used for treatment of acute myeloid leukemia (AML) 8 .…”

Section: Introductionmentioning

confidence: 99%

“…Moxonidine is a new generation antihypertensive drug containing imidazole moiety 8 . Tipifarnib is an imidazole derivative which used for treatment of acute myeloid leukemia (AML) 8 . Thiohydantoins, is well known due their amazing applications as human immunodefi ciency virus (HIV) 9, 10 , antimutagenic 12,13 , anticarcinogenic 14 , anti-microbial 15-17 , anti-viral 18 , hypolipidemic 19,20 , anti-thyroidal 21- 23 and tuberculosis 24 , anti-ulcer, anti-infl ammatory agents 25 , and pesticides 26 .…”

Section: Introductionmentioning

confidence: 99%

Green synthesis of thioxoimidazolidine derivative ligand: Spectroscopic, thermal and biological assignments of new Cu(II), Co(II), and Ni(II) chelates in neutral system

Alosaimi

Saad

Refat

et al. 2021

Polish Journal of Chemical Technology

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Eco-friendly synthesis of ethyl 3-(4-oxo-3-(1-(pyridin-3-yl)ethylideneamino)-2-thioxoimidazolidin-1-yl)propanoate (4) ligand (L) using microwave irradiation technique was described. The structure of thioxoimidazolidine derivative ligand compound has been established based on different types of analyses such as infrared, 1H-NMR, 13C-NMR, and mass spectra as well as elemental analysis. The copper, cobalt, and nickel(II) complexes with molecular formula [M(L)(H2O)4]Cl2 (where M = Co(II), Ni(II), and Cu(II), L = thioxoimidazolidine derivative ligand), have been prepared and well-characterized using microanalytical, conductivity measurements, magnetic, spectroscopic, and physical analyses. Upon the outcome results of analyses, the stoichiometry of the synthesized complexes is 1:1 (M:L). The molar conductance values concluded that the behavior of metal complexes was electrolytes. The 3-(4-oxo-3-(1-(pyridin-3-yl)ethylideneamino)-2-thioxoimidazolidin-1-yl)propanoate chelate acts as a monovalent bidentate fashion via nitrogen and oxygen atoms of both thioxoimidazolidine and propanoate ester moieties. The geometric structures of the synthesized metal complexes are an octahedral configuration based on spectroscopic and magnetic moment studies. The thermogravimetric assignments deduced that the presence of four coordinated water molecules. The synthesized copper(II), cobalt(II), and nickel(II) complexes were biologically checked against G+ and G- bacteria and two species of fungi (Aspergillus Nigaer, and Penicillium Sp.).

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Synthesis and Antimicrobial Activity of Fluorine Containing Pyrazole-clubbed Dihydropyrimidinones

Cited by 24 publications

References 37 publications

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Design, synthesis, antimicrobial evaluation, and in‐silico studies of some 4‐thiazolidinone hybrids bearing coumarin and pyridine moieties

Green synthesis of thioxoimidazolidine derivative ligand: Spectroscopic, thermal and biological assignments of new Cu(II), Co(II), and Ni(II) chelates in neutral system

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