Synthesis and Biological Activity of 4-(Pyridin-3-yl)-2-hydroxy-4-oxobut-2-enoic Acid Derivatives

Synlett ◽  
2019 ◽  
Vol 31 (02) ◽  
pp. 165-170
Author(s):  
Alena L. Oleshchuk ◽  
Zarina T. Shulgau ◽  
Tulegen M. Seilkhanov ◽  
Alexey S. Vasilchenko ◽  
Samat A. Talipov ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Biological Activity ◽  
Condensation Reaction ◽  
Enoic Acid ◽  
Diethyl Oxalate ◽  
Pyrazole Derivatives ◽  
Biological Screening ◽  
Claisen Condensation

Claisen condensation reaction of diethyl oxalate with 1-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]ethan-1-one afforded (Z)-4-[4-(furan-2-yl)-2-methyl-5-nitro-6-phenylpyridin-3-yl]-2-hydroxy-4-oxobut-2-enoic acid. The latter reacted with various binucleo­philes to form the corresponding 3,4-dihydroquinoxaline-2(1H)-one, 3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one, and 1H-pyrazole derivatives. Biological screening of the obtained compounds revealed analgesic and antibacterial activity.

scholarly journals Synthesis, Characterization, and Evaluation for Antibacterial and Antifungal Activities of N-Heteroaryl Substituted Benzene Sulphonamides

2014 ◽  
Vol 2014 ◽  
pp. 1-5 ◽  
Author(s):  
Christiana Nonye Igwe ◽  
Uchechukwu Chris Okoro
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Biological Activity ◽  
Condensation Reaction ◽  
Salmonella Typhi ◽  
Heteroaromatic Compounds ◽  
E Coli ◽  
Antibacterial And Antifungal Activities ◽  
Target Molecules ◽  
Antibacterial And Antifungal

The synthesis and biological activity of N-heteroaryl substituted benzene sulphonamides (3a–h) were successful. Simple condensation reaction of benzene sulphonyl chloride (1) with substituted heteroaromatic compounds (2a–h) under dry pyridine and acetone gave the target molecules (3a–h) in good to excellent yield. The compounds were characterized using FTIR, 1HNMR, and 13CNMR. The compounds were screened for antibacterial activity against E. coli, Salmonella typhi, P. aeruginosa, B. cereus, K. pneumonia, and Sarcina  lutea and antifungal activity against C. albicans and A. niger. The results of the antimicrobial activity showed improved biological activity against some tested organisms.

Complexes of Cu (II) with a-Ketoglutaric Acid and 1- (o-tolyl) Biguanide Synthesis, characterization and biological Activity

2019 ◽  
Vol 70 (10) ◽  
pp. 3603-3610
Author(s):  
Madalina Mihalache ◽  
Cornelia Guran ◽  
Aurelia Meghea ◽  
Vasile Bercu ◽  
Ludmila Motelica ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Pseudomonas Aeruginosa ◽  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Biological Activity ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Copper Complexes ◽  
Substrate Adhesion ◽  
Inert Substrate

The three copper complexes having a-ketoglutaric acid (H2A) and 1- (o-tolyl) biguanide (TB) ligands have been synthesized and characterized. The proposed formulas for these complexes are: [Cu(TB)(HA)]Cl (C1), [Cu(TB)(HA)CH3COO]�H2O (C2) and [Cu(TB)(HA)](NO3) (C3) where HA represents deprotonated H2A. The complexes obtained were tested for antibacterial activity against Staphylococcus aureus ATCC 25923 and Pseudomonas aeruginosa ATCC 27853, antifungal activity on Candida albicans ATCC 10231 and antitumor activity on HeLa tumor cells. Due to the antitumor, antifungal, antimicrobial activity and inhibition of inert substrate adhesion, complexes synthesized could be used for potential therapeutic applications.

Microwave assisted synthesis of novel Pyrazole derivatives and their biological evaluation as anti-bacterial agents

2020 ◽  
Vol 23 ◽  
Author(s):  
Hadis Khodadad ◽  
Farhad Hatamjafari ◽  
Khalil Pourshamsian ◽  
Babak Sadeghi
Keyword(s):  
Antibacterial Activity ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Antibacterial Activities ◽  
Structural Features ◽  
Biological Evaluation ◽  
Aureus Strain ◽  
Microwave Assisted Synthesis ◽  
Pyrazole Derivatives ◽  
Microwave Assisted

Aim and Objective: Microwave-assisted condensation of acetophenone 1 and aromatic aldehydes 2 gave chalcone analogs 3, which were cyclized to pyrazole derivatives 6a-f via the reaction with hydrazine hydrate and oxalic acid in the presence of the catalytic amount of acetic acid in ethanol. Materials and Methods: The structural features of the synthesized compounds were characterized by melting point, FT-IR, 1H, 13C NMR and elemental analysis. Results: The antibacterial activities of the synthesized pyrazoles was evaluated against three gram-positive bacteria such as Enterococcus durans, Staphylococcus aureus, Bacillus subtilis and two gram-negative bacteria such as Escherichia coli and Salmonella typhimurium. Conclusion: All the synthesized pyrazoles showed relatively high antibacterial activity against S. aureus strain and none of them demonstrated antibacterial activity against E. coli.

Structure-Activity Relationship and Antimicrobial Evaluation of N-Phenylpyrazole Curcumin Derivatives

2020 ◽  
Vol 16 (4) ◽  
pp. 481-488
Author(s):  
Heli Sanghvi ◽  
Satyendra Mishra
Keyword(s):  
Antibacterial Activity ◽  
Gram Negative Bacteria ◽  
Pyrazole Derivatives ◽  
Gram Positive ◽  
Gram Negative ◽  
E Coli ◽  
Curcumin Derivatives ◽  
Structure Activity ◽  
Electron Donating Groups ◽  
Derivatives Of

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.

scholarly journals New Mononuclear and Binuclear Cu(II), Co(II), Ni(II), and Zn(II) Thiosemicarbazone Complexes with Potential Biological Activity: Antimicrobial and Molecular Docking Study

Molecules ◽  
2021 ◽  
Vol 26 (8) ◽  
pp. 2288
Author(s):  
Ahmed Gaber ◽  
Moamen S. Refat ◽  
Arafa A.M. Belal ◽  
Ibrahim M. El-Deen ◽  
Nader Hassan ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Biological Activity ◽  
Molecular Docking ◽  
Metal Complexes ◽  
Analytical Data ◽  
Docking Study ◽  
Spectroscopic Techniques ◽  
Molecular Docking Study ◽  
Tetrahedral Geometry ◽  
Thiosemicarbazone Complexes

Herein, we report the synthesis of eight new mononuclear and binuclear Co2+, Ni2+, Cu2+, and Zn2+ methoxy thiosemicarbazone (MTSC) complexes aiming at obtaining thiosemicarbazone complex with potent biological activity. The structure of the MTSC ligand and its metal complexes was fully characterized by elemental analysis, spectroscopic techniques (NMR, FTIR, UV-Vis), molar conductivity, thermogravimetric analysis (TG), and thermal differential analysis (DrTGA). The spectral and analytical data revealed that the obtained thiosemicarbazone-metal complexes have octahedral geometry around the metal center, except for the Zn2+-thiosemicarbazone complexes, which showed a tetrahedral geometry. The antibacterial and antifungal activities of the MTSC ligand and its (Co2+, Ni2+, Cu2+, and Zn2+) metal complexes were also investigated. Interestingly, the antibacterial activity of MTSC- metal complexes against examined bacteria was higher than that of the MTSC alone, which indicates that metal complexation improved the antibacterial activity of the parent ligand. Among different metal complexes, the MTSC- mono- and binuclear Cu2+ complexes showed significant antibacterial activity against Bacillus subtilis and Proteus vulgaris, better than that of the standard gentamycin drug. The in silico molecular docking study has revealed that the MTSC ligand could be a potential inhibitor for the oxidoreductase protein.

Structural, QSAR, machine learning and molecular docking studies of 5-thiophen-2-yl pyrazole derivatives as potent and selective cannabinoid-1 receptor antagonists

2021 ◽  
Author(s):  
Riad Hanachi ◽  
Ridha Ben Said ◽  
Hamza Allal ◽  
Seyfeddine Rahali ◽  
Mohammed A. M. Alkhalifah ◽  
...  
Keyword(s):  
Machine Learning ◽  
Biological Activity ◽  
Molecular Docking ◽  
Theoretical Analysis ◽  
Structural Study ◽  
Docking Studies ◽  
Pyrazole Derivatives ◽  
Molecular Docking Studies ◽  
Cannabinoid 1 Receptor ◽  
Chemical Descriptors

We performed a structural study followed by a theoretical analysis of the chemical descriptors and the biological activity of a series of 5-thiophen-2-yl pyrazole derivatives as potent and selective Cannabinoid-1...

scholarly journals A New Supported Manganese-Based Coordination Complex as a Nano-Catalyst for the Synthesis of Indazolophthalazinetriones and Investigation of Its Antibacterial Activity

Chemistry ◽  
2021 ◽  
Vol 3 (3) ◽  
pp. 783-799
Author(s):  
Maryam Ariannezhad ◽  
Davood Habibi ◽  
Somayyeh Heydari ◽  
Vahideh Khorramabadi
Keyword(s):  
Antibacterial Activity ◽  
Simple Procedure ◽  
Condensation Reaction ◽  
Antibacterial Properties ◽  
Coordination Complex ◽  
Bacterial Strains ◽  
One Pot ◽  
Nano Catalyst ◽  
Ft Ir ◽  
The One

A new magnetic supported manganese-based coordination complex (Fe3O4@SiO2@CPTMS@MBOL@ Mn) was prepared in consecutive stages and characterized via various techniques (VSM, SEM, TEM, XRD, FT-IR, EDX, TG-DTA, and ICP). To evaluate its application, it was used for synthesis of divers Indazolophthalazinetriones in a simple procedure via the one-pot three-component condensation reaction of aldehydes, dimedone, and phthalhydrazide in ethanol under reflux conditions. The Mn catalyst can be recycled without any noticeable loss in catalytic activity. Additionally, the antibacterial properties of the nano-catalyst were studied against some bacterial strains.

Biological Activity of Novel N-Substituted Amides of endo-3- (3-Methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene-2- carboxylic Acid and N-Substituted Amides of 1-(5-Methylthio- 1,2,4-triazol-3-yl)cyclohexane-2-carboxylic Acids

2012 ◽  
Vol 67 (3-4) ◽  
pp. 123-128
Author(s):  
Anna Pachuta-Stec ◽  
Urszula Kosikowska ◽  
Anna Chodkowska ◽  
Monika Pitucha ◽  
Anna Malm ◽  
...  
Keyword(s):  
Biological Activity ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Condensation Reaction ◽  
Primary Amines ◽  
Pharmacological Activities

N-Substituted amides of endo-3-(3-methylthio-1,2,4-triazol-5-yl)bicyclo[2.2.1]hept-5-ene- 2-carboxylic acid and 1-(5-methylthio-1,2,4-triazol-3-yl)cyclohexane-2-carboxylic acid were prepared by the condensation reaction of endo-S-methyl-N1-(bicyclo[2.2.1]hept-5-ene-2,3- dicarbonyl)isothiosemicarbazide and S-methyl-N1-(cyclohexane-2,3-dicarbonyl)isothiosemicarbazide with primary amines. The synthesized compounds were screened for their microbiological and pharmacological activities

scholarly journals Synthesis of 14-Substituted-14H-Dibenzo[a,j]Xanthene Derivatives in Presence of Effective Synergetic Catalytic System Bleaching Earth Clay and PEG-600

Catalysts ◽  
2021 ◽  
Vol 11 (11) ◽  
pp. 1294
Author(s):  
Sandeep T. Atkore ◽  
Giribala M. Bondle ◽  
Pranita V. Raithak ◽  
Vinod T. Kamble ◽  
Ravi Varala ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Pseudomonas Aeruginosa ◽  
Antibacterial Activity ◽  
Catalytic System ◽  
Present Method ◽  
Condensation Reaction ◽  
Bleaching Earth ◽  
Product Yield ◽  
Xanthene Derivatives ◽  
Peg 600

The synthesis of 14-aryl 14H-dibenzo[a,j]xanthenes is achieved by a simple condensation reaction between β-naphthol with aryl or alkyl aldehydes in an effective synergetic catalytic system created by combining basic bleaching earth clay and PEG-600. The advantages of the present method include catalyst recyclability, superior product yield, a shorter reaction time and the avoidance of hazardous reagents. Synthesized xanthene derivatives were also screened for their antibacterial activity against Staphylococcus aureus (MTCC 96) and Pseudomonas aeruginosa (Wild).

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