scholarly journals Synthesis and biological activity of 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide derivatives

ADMET & DMPK ◽  
2021 ◽  
Author(s):  
Svetlana Meshcheryakova ◽  
Alina Shumadalova ◽  
Ozal Beylerli ◽  
Ilgiz Gareev
Keyword(s):  
Antimicrobial Agents ◽  
Biologically Active ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial Screening ◽  
Microbial Inhibition ◽  
Antimicrobial Evaluation ◽  
Temperature Interaction ◽  
Antibacterial And Antifungal ◽  
New Compounds ◽  
Base Object

The synthesis and antimicrobial evaluation of new 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide derivatives was investigated. According to the literature, there are a lot of antimicrobial agents among the pyrimidines and hydrazides, and therefore it seems promising to use 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide as a base object for synthesizing new biologically active substances. 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide was obtained by the hydrazinolysis of ethyl thioacetate, using a 3-fold molar excess of 85 % hydrazine hydrate in ethanol, at room temperature. Interaction of 2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]­acetohydrazide with ketones during boiling in ethanol yielded N-ylidenehydrazides. The solid obtained by concentration was collected, and then purified by recrystallization. The new compounds were characterized by 1H, 13C NMR, IR spectroscopy and elemental analysis. The antibacterial and antifungal activities of the new compounds were analysed using agar diffusion and tenfold broth (pH 7.2 – 7.4) dilution methods, in comparison with the clinical used drugs, ceftriaxone and Pimafucin. The structure–activity studies showed that, depending on the nature of the hydrazide fragment, the newly synthesized compounds exhibited varying degrees of microbial inhibition. Within the same series the antimicrobial activity depends on the nature of the substituent attached to the benzene ring. The investigation of antibacterial screening data revealed that the compounds Nʹ-[1-(4-aminophenyl)ethylidene]-2-[6-methyl-4-(thietan-3-yloxy)pyrimidin-2-ylthio]acetohydrazide, Nʹ-[1-(4-hydroxyphenyl)ethylidene]-2-[6-methyl-4-(thi­­etan­-3-yloxy)pyrimidin-2-ylthio]acetohydrazide, Nʹ-[1- (2,5-dihydroxyphenyl) ethylidene]-2-[6-methyl-4-(thietan-3-yloxy)-pyrimidin-2-ylthio]acetohydrazide were found to be more potent than the other synthesized analogues.

scholarly journals Synthesis, structural characterization and antimicrobial evaluation of some novel piperidin-4-one oxime esters

2015 ◽  
Vol 80 (9) ◽  
pp. 1101-1111 ◽  
Author(s):  
Gokula Krishnan ◽  
R. Sivakumar ◽  
V. Thanikachalam
Keyword(s):  
Biologically Active ◽  
Good Activity ◽  
Mass Spectral ◽  
Antibacterial And Antifungal Activities ◽  
Xrd Study ◽  
Antimicrobial Evaluation ◽  
Ft Ir ◽  
Antibacterial And Antifungal

Fifteen novel biologically active piperidin-4-one oxime esters (8-22) have been synthesized with good yields. These compounds were prepared from in-situ activated carboxylic acids using POCl3 and pyridine with piperidin-4- one oximes. The structure of the title compounds were elucidated on the basis of FT-IR, NMR (1D and 2D) and mass spectral analyses. The single crystal XRD study of compounds 12 and 20 were the further evidence for the proposed structure unambiguously. All the synthesized compounds were tested for in vitro antibacterial and antifungal activities. Many of these derivatives exhibited good activity against Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli, Trigoderma veride and Aspergillus flavus.

A New Reactive Ketenaminal: Synthesis, Coupling Reaction, Tautomeric Study, Docking and Antimicrobial Evaluation of the Products

2020 ◽  
Vol 16 (6) ◽  
pp. 761-773
Author(s):  
Huda K. Mahmoud ◽  
Hanadi A. Katouah ◽  
Marwa F. Harras ◽  
Thoraya A. Farghaly
Keyword(s):  
Binding Site ◽  
Antimicrobial Agents ◽  
Coupling Reaction ◽  
Docking Study ◽  
Binding Mode ◽  
Binding Energies ◽  
Simple Method ◽  
Antimicrobial Evaluation ◽  
New Compounds ◽  
Active Methylene

Background: One of the most successful reagents used in the synthesis of the reactive enaminone is DMF-DMA, but it is very expensive with harmful effects on the human health and reacts with special compounds to generate the enaminone such as active methylene centers. Aim: In this article, we synthesized a new ketenaminal by simple method with inexpensive reagents (through desulfurization in diphenylether). Methods: Thus, a novel reactive ketenaminal (enaminone) was synthesized from the desulfurization of 2-((2-(4-chlorophenyl)-2-oxoethyl)thio)-5,7-bis(4-methoxyphenyl)pyrido[2,3-d]pyrimidin- 4(3H)-one with diphenylether. The starting keteneaminal was coupled with diazotized anilines via the known coupling conditions to give a new series of 2-(4-chlorophenyl)-1-(2-(arylhydrazono)-2- oxoethyl)-5,7-bis(4-methoxy-phenyl)pyrido[2,3-d]pyrimidin-4(1H)-ones. Results: The structures of the new compounds were elucidated based on their IR, 1H-NMR, 13CNMR, and Mass spectra. Moreover, the potency of these compounds as antimicrobial agents has been evaluated. The results showed that some of the products have high activity nearly equal to that of the used standard antibiotic. Additionally, the docking study was done to get the binding mode of the synthesized compounds with the binding site of the DHFR enzyme. The results of molecular docking of the synthesized arylhydrazono compounds are able to fit in DHFR binding site with binding energies ranging from -4.989 to -8.178 Kcal/mol. Conclusion: Our goal was achieved in this context by the synthesis of new ketenaminal from inexpensive reagents, which was utilized in the preparation of bioactive arylhydrazone derivatives.

scholarly journals Development of Antibacterial and Antifungal Triazole Chromium(III) and Cobalt(II) Complexes: Synthesis and Biological Activity Evaluations

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 2013 ◽  
Author(s):  
Ricardo Murcia ◽  
Sandra Leal ◽  
Martha Roa ◽  
Edgar Nagles ◽  
Alvaro Muñoz-Castro ◽  
...  
Keyword(s):  
Electrical Conductivity ◽  
Biological Activity ◽  
Melting Point ◽  
Inhibitory Concentration ◽  
Vero Cells ◽  
Visible Spectroscopy ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal ◽  
New Compounds

In this work, six complexes (2–7) of Cr(III) and Co(II) transition metals with triazole ligands were synthesized and characterized. In addition, a new ligand, 3,5-bis(1,2,4-triazol-1-ylmethyl)toluene (1), was synthesized and full characterized. The complexes were obtained as air-stable solids and characterized by melting point, electrical conductivity, thermogravimetric analysis, and Raman, infrared and ultraviolet/visible spectroscopy. The analyses and spectral data showed that complexes 3–7 had 1:1 (M:L) stoichiometries and octahedral geometries, while 2 had a 1:2 (M:L) ratio, which was supported by DFT calculations. The complexes and their respective ligands were evaluated against bacterial and fungal strains with clinical relevance. All the complexes showed higher antibacterial and antifungal activities than the free ligands. The complexes were more active against fungi than against bacteria. The activities of the chromium complexes against Candida tropicalis are of great interest, as they showed minimum inhibitory concentration 50 (MIC50) values between 7.8 and 15.6 μg mL−1. Complexes 5 and 6 showed little effect on Vero cells, indicating that they are not cytotoxic. These results can provide an important platform for the design of new compounds with antibacterial and antifungal activities.

scholarly journals Development of new 5-chromenyl-2,4-thiazolidinediones as antimicrobial agents

2015 ◽  
Vol 89 (1) ◽  
pp. 122-127 ◽  
Author(s):  
Cristina Mariana Nastasă ◽  
Mihaela Duma ◽  
Adrian Pîrnău ◽  
Laurian Vlase ◽  
Brîndușa Tiperciuc ◽  
...  
Keyword(s):  
Antimicrobial Agents ◽  
Treatment Strategies ◽  
Inhibition Zone ◽  
Diffusion Method ◽  
Future Research ◽  
Physico Chemical ◽  
New Chemical Entities ◽  
New Treatment ◽  
Antibacterial And Antifungal ◽  
New Compounds

Background and aims. In the context of the increasing phenomenon of microbial resistance to usual drugs, the development of new treatment strategies and new therapeutic protocols is a constant need. Thiazolidinedione and chromone represent two important scaffolds in medicinal chemistry due to their large pharmacological applicability.Methods. We synthesized a new 5-(chromene-3-yl)methylene-2,4-thiazolidinedione starting from 6,8-dichloro-4-oxo-4H-chromene-3-carbaldehyde. Then, by treating with different α-bromoalkylarylketones, we obtained N-substituted derivatives. All new compounds were investigated for their antimicrobial potential, using the diffusion method, against Listeria monocytogenes ATCC 13932, Staphylococcus aureus ATCC 49444, Escherichia coli ATCC 25922, Salmonella typhimurium ATCC 14028 and Candida albicans ATCC 10231. Three concentrations, 10 mg/ml, 5 mg/ml and 1 mg/ml of compounds were used. The results were evaluated by the measurement of the inhibition zone diameters and compared to those of gentamicin and fluconazole respectively, as reference drugs.Results. All new synthesized compounds were characterized using physico-chemical and spectrometric methods. They displayed modest to good antimicrobial activity. New molecules 8, 9 and 10 may represent promising candidates, showing zone inhibition diameters superior to those of reference drugs.Conclusions. This work presents chemical synthesis, characterization and investigation of the antibacterial and antifungal potential of 5-(chromene-3-yl)methylene-2,4-thiazolidinedione derivatives, which may be worthy of future research for designing new chemical entities.

scholarly journals Synthesis, Characterization and Molecular Docking of 1,2,4-Triazole Derivatives as Potential Antimicrobial Agents

2020 ◽  
Vol 32 (6) ◽  
pp. 1437-1442
Author(s):  
Panneerselvam Kalaivani ◽  
Jayaraman Arikrishnan ◽  
Mannuthusamy Gopalakrishnan
Keyword(s):  
Antimicrobial Agents ◽  
Docking Study ◽  
Binding Mode ◽  
Zone Of Inhibition ◽  
Mass Spectral ◽  
Antibacterial And Antifungal Activities ◽  
Inhibition Concentration ◽  
Ft Ir ◽  
Antibacterial And Antifungal

In this study, a new series of (E)-N-(4-(3-(3,5-dialkylphenyl)acryloyl)phenyl)-2-(1H-1,2,4-triazol-1- yl)acetamide (32-41) was synthesized, characterized by FT-IR, 1H NMR, 13C NMR and Mass spectral analysis and evaluated for their in vitro antibacterial and antifungal activities. The docking study of the newly synthesized compounds was performed and results showed good binding mode in the active site of 1T9U protein. The zone of inhibition concentration was tested for the synthesized compounds against five bacterial and three fungal strains. Compounds 34 and 37 have good antibacterial activity. Compounds 3, 4 and 6 shows moderate inhibition against the antifungal activity.

scholarly journals Synthesis and Antimicrobial Activity of Some Chalcone Derivatives

2008 ◽  
Vol 5 (3) ◽  
pp. 461-466 ◽  
Author(s):  
Y. Rajendra Prasad ◽  
A. Lakshmana Rao ◽  
R. Rambabu
Keyword(s):  
Aqueous Solution ◽  
Antimicrobial Activity ◽  
Potassium Hydroxide ◽  
Room Temperature ◽  
Antimicrobial Agents ◽  
Aromatic Aldehydes ◽  
Plate Method ◽  
H Nmr ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal

In an effort to develop antimicrobial agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with appropriate aromatic aldehydes in the presence of aqueous solution of potassium hydroxide and ethanol at room temperature. The synthesized compounds were characterized by means of their IR,1H-NMR spectral data and elemental analysis. All the compounds were tested for their antibacterial and antifungal activities by the cup plate method.

scholarly journals Design, Synthesis, and Antimicrobial Evaluation of Novel Pyrazoles and Pyrazolyl 1,3,4-Thiadiazine Derivatives

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2092 ◽  
Author(s):  
Ibrahim Radini
Keyword(s):  
Antimicrobial Activity ◽  
Minimum Inhibitory Concentration ◽  
Elemental Analysis ◽  
Inhibitory Concentration ◽  
Diazonium Salts ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
Antimicrobial Evaluation ◽  
Antibacterial And Antifungal

A novel series of pyrazolyl 1,3,4-thiadiazines 5a–c, 8a–c, 12, 15a–c, 17a–c, and 20 was prepared from the reaction of pyrazole-1-carbothiohydrazide 1a,b with 2-oxo-N′-arylpropanehydrazonoyl chloride, 2-chloro-2-(2-arylhydrazono)acetate, and 3-bromoacetylcoumarin. Moreover, the regioselective reaction of 5-pyrazolone-1-carbothiohydrazide 1a with 4-substituted diazonium salts and 4-(dimethylamino)benzaldehyde gave the corresponding hydrazones 21a–c and 22. The newly prepared compounds were characterized by spectroscopy and elemental analysis. Many new synthesized compounds showed considerable antimicrobial activity against tested microorganisms. Hydrazones 21a–c and 22 showed remarkable antibacterial and antifungal activities. 4-(2-(p-tolyl)hydrazineylidene)-pyrazole-1-carbothiohydrazide 21a displayed the highest antibacterial and antifungal activities with minimum inhibitory concentration (MIC) values lower than standard drugs chloramphenicol and clotrimazole, in the range of 62.5–125 and 2.9–7.8 µg/mL, respectively.

scholarly journals Comprehensive Evaluation of the Antibacterial and Antifungal Activities of Carlina acaulis L. Essential Oil and Its Nanoemulsion

Antibiotics ◽  
2021 ◽  
Vol 10 (12) ◽  
pp. 1451
Author(s):  
Antonio Rosato ◽  
Alexia Barbarossa ◽  
Ahmed M. Mustafa ◽  
Giulia Bonacucina ◽  
Diego Romano Perinelli ◽  
...  
Keyword(s):  
Essential Oil ◽  
Comprehensive Evaluation ◽  
Antimicrobial Properties ◽  
Homogenization Method ◽  
Bacterial Strains ◽  
Antifungal Activities ◽  
Fungal Strains ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal ◽  
New Compounds

Plants are considered to be an excellent source of new compounds with antibiotic activity. Carlina acaulis L. is a medicinal plant whose essential oil (EO) is mainly characterized by the polyacetylene carlina oxide, which has antimicrobial properties. The aim of this study was to evaluate the antimicrobial and antifungal activities of C. acaulis EO, carlina oxide, and nanoemulsion (NE) containing the EO. The EO was obtained through plant roots hydrodistillation, and carlina oxide was purified from it through silica gel column chromatography. The NE containing C. acaulis EO was prepared with the high-pressure homogenization method, and the minimum inhibitory concentration (MIC) was determined against several bacterial and fungal strains for all the C. acaulis-derived products. The latter resulted in activity active versus all the screened Gram-positive bacterial strains and also on all the fungal strains with low MIC values. For yeast, the EO and carlina oxide showed good MIC values. The EO-NE demonstrated a better activity than the pure EO on all the tested bacterial and fungal strains. The results suggest that C. acaulis-derived products could be potential candidates for the development of natural antibacterial and antifungal agents.

scholarly journals Synthesis, Antibacterial and Antifungal Evlaution of Novel Pyrazoline Derivatives

2018 ◽  
Vol 17 (2) ◽  
pp. 221-226
Author(s):  
BC Revanasiddappa ◽  
MS Jisha ◽  
M Vijay Kumar ◽  
Hemanth Kumar
Keyword(s):  
Good Activity ◽  
Bacterial Strains ◽  
Mass Spectral Data ◽  
Acetic Acid Medium ◽  
Mass Spectral ◽  
Antibacterial And Antifungal Activities ◽  
Alcohol Medium ◽  
Antibacterial And Antifungal ◽  
New Compounds

A new series of chalcones (2a-j) were prepared by reacting substituted aldehydes and substituted ketones in alcohol medium in presence of NaOH. The chalcones underwent selective cyclization with guanicol hydrazide (1) in glacial acetic acid medium to yield the title compounds 1,3,5-trisubstituted pyrazolines (3a-j). The new compounds were characterized on the basis of 1H-NMR, IR and mass spectral data. All the newly synthesized compounds were evaluated for their in-vitro antibacterial and antifungal activities. Some of the tested compounds 3a and 3e showed good activity against bacterial strains and compounds 3d and 3h revealed good activity against fungal strains. Dhaka Univ. J. Pharm. Sci. 17(2): 221-226, 2018 (December)

scholarly journals DESIGN, SYNTHESIS OF BIOLOGICALLY ACTIVE HETEROCYCLES CONTAINING INDOL- THIAZOLYL- THIAZOLIDINONE DERIVATIVES

2018 ◽  
Vol 11 (3) ◽  
pp. 113 ◽  
Author(s):  
Prabhakar Walmik ◽  
Basavaraj S Naraboli ◽  
Swathi B ◽  
Somashekhar Ghanti
Keyword(s):  
Analytical Data ◽  
Biologically Active ◽  
Design Synthesis ◽  
Mass Spectral ◽  
Antibacterial And Antifungal Activities ◽  
Microdilution Method ◽  
13C Nuclear Magnetic Resonance ◽  
Broth Microdilution Method ◽  
Antibacterial And Antifungal

 Objective: The present study envisage a novel series of thiazole, indole and thiazolidine derivatives, namely, N-((5-Substituted-2-phenyl-1 H-indol-3-yl)methylene)-4,5,6,7-tetrahydro-5,7,-dimethylbenzo [d]thiazole-2-amine (4a-c), 2-(5-substituted-2-phenyl-1H-indol-3-yl)-3-(4,5,6,7- trimethylbenzo[d]thiazol-2-yl)-thiazolidin-4-one (5a-c) and 5-benzylidine-2-(5-substituted-2phenyl-1H-indol-3yl)-3-(4,5,6,7-tetrahydro-5,5,7- trimethylbenzo[d]thiazol-2-yl) thiazolidin-4-one (6a-c).Methods: All the newly synthesized compounds were characterized by infrared, 1H, 13C nuclear magnetic resonance and mass spectral data and elemental analysis and evaluated for in vitro antimicrobial activity.Results: Novel compounds N-((5-Substituted-2-phenyl-1H-indol-3-yl)methylene)-4,5,6,7-tetrahydro-5,7,-dimethylbenzo [d]thiazole-2-amine (4a-c), 2-(5-substituted-2-phenyl-1H-indol-3-yl)-3-(4,5,6,7-trimethylbenzo[d]thiazol-2-yl)-thiazolidin-4-one (5a-c) and 5-benzylidine-2-(5-substituted- 2phenyl-1H-indol-3yl)-3-(4,5,6,7-tetrahydro-5,5,7-trimethyl benzo[d]thiazol-2-yl)thiazolidin-4-one (6a-c) have been made and characterized using spectral and analytical data. The results of antibacterial and antifungal activities showed that some of the synthesized compounds exhibited promising activities.Conclusion: All the newly synthesized compounds were carried out by the broth microdilution method (NCCLS. 2002) in a DMF concentration of 500, 250, 125, and 62.5 μg/ml. Gentamycin and fluconazole are used as reference standards for antibacterial and antifungal activity, respectively. The final results revealed that compounds 4b, 5b, and 6b exhibited potent antimicrobial activity when compared to the standard drugs. 

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