An efficient synthesis of some new chalcone, acetyl pyrazoline and amino pyrimidine bearing 1,3,5- triazine nucleus as potential antimicrobial and antitubercular agent

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Antimicrobial Activity ◽  
Guanidine Hydrochloride ◽  
Antitubercular Activity ◽  
Dilution Method ◽  
Mycobacterium Tuberculosis H37rv ◽  
New Class ◽  
Chemical Structures ◽  
Lowenstein Jensen ◽  
Amino Pyrimidine

In an attempt to find a new class of antimicrobial and antitubercular agent, a new series of chalcone, acetyl pyrazoline and amino pyrimidine bearing 1,3,5- triazine nucleus were synthesized with appropriate chemical reagent. Chalcones (D1-D5) were synthesized by the classical Claisen-Schmidt condensation of substituted ketone (C) with variously substituted aldehydes via conventional method. Now treatment of chalcones with hydrazine hydrate/glacial acetic acid and guanidine hydrochloride/Alkali afforded the corresponding acetyl pyrazoline (E1-E5) and amino pyrimidine (F1-F5) derivatives respectively. The chemical structures of all newly synthesized compounds were established on the basis of their FTIR, 1H NMR, 13C NMR, LC-MS as well as elemental analysis. All the newly design compounds were assayed for their in vitro antimicrobial activity against selected pathogens by the Broth dilution method and in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv using Lowenstein-Jensen MIC method. Most of the compounds showed appreciable antimicrobial activity against the all tested strains. Among the synthesized compounds D1, D2, D3, E1, E3, E4, F3 and F4 exhibited excellent antimicrobial activity and said to be the most proficient members of the series. Compound D5 and F5 exhibited promising antitubercular activity.

scholarly journals e-Pharmacophore model-guided design of potential DprE1 inhibitors: synthesis, in vitro antitubercular assay and molecular modelling studies

2021 ◽  
Author(s):  
Avinash Kumar ◽  
Revathi Rajappan ◽  
Suvarna G. Kini ◽  
Ekta Rathi ◽  
Sriram Dharmarajan ◽  
...  
Keyword(s):  
Pharmacophore Model ◽  
Antitubercular Activity ◽  
Stable Complex ◽  
Dilution Method ◽  
Agar Dilution Method ◽  
Standard Drug ◽  
Docking Score ◽  
Mycobacterium Tuberculosis H37rv ◽  
Cytotoxicity Studies

AbstractTuberculosis continues to wreak havoc worldwide and caused around 1.4 million deaths in 2019. Hence, in our pursuit of developing novel antitubercular compounds, we are reporting the e-Pharmacophore-based design of DprE1 (decaprenylphosphoryl-ribose 2′-oxidase) inhibitors. In the present work, we have developed a four-feature e-Pharmacophore model based on the receptor–ligand cavity of DprE1 protein (PDB ID 4P8C) and mapped our previous reported library of compounds against it. The compounds were ranked on phase screen score, and the insights obtained from their alignment were used to design some novel compounds. The designed compounds were docked with DprE1 protein in extra-precision mode using Glide module of Maestro, Schrodinger. Some derivatives like B1, B2, B4, B5 and B12 showed comparable docking score (docking score > − 6.0) with respect to the co-crystallized ligand. The designed compounds were synthesized and characterized. In vitro antitubercular activity was carried out on Mycobacterium tuberculosis H37Rv (ATCC27294) strain using the agar dilution method, and minimum inhibitory concentration (MIC) was determined. The compound B12 showed a MIC value of 1.56 μg/ml which was better than the standard drug ethambutol (3.125 μg/ml). Compounds B7 and B11 were found to be equipotent with ethambutol. Cytotoxicity studies against Vero cell lines proved that these compounds were non-cytotoxic. Molecular dynamic simulation study also suggests that compound B12 will form a stable complex with DprE1 protein and will show the crucial H-bond interaction with LYS418 residue. Further in vitro enzyme inhibition studies are required to validate these findings.

An Efficient Synthesis and Antimicrobial Evaluation of some New Pyrazoline, Pyrimidine and Benzodiazepine Derivatives Bearing 1,3,5-Triazine Core

2015 ◽  
Vol 57 ◽  
pp. 13-24 ◽  
Author(s):  
Anjani Solankee ◽  
Riki Tailor
Keyword(s):  
Guanidine Hydrochloride ◽  
Antibacterial Activities ◽  
Dilution Method ◽  
Mass Spectral ◽  
E Coli ◽  
H Nmr ◽  
Antimicrobial Evaluation ◽  
Benzodiazepine Derivatives ◽  
Amino Pyrimidine

In our present investigation a new class of diverse sets of acetyl pyrazolines (6a-e), amino pyrimidines (7a-e) and 1,5-benzodiazepines (8a-e) bearing 1,3,5-triazine core were synthesised from chalcones (5a-e). Treatment of chalcone with hydrazine hydrate, guanidine hydrochloride and o-phenylenediamine afforded the corresponding acetyl pyrazoline, amino pyrimidine and 1,5-benzodiazepine derivatives respectively. The structures of all the newly synthesised compounds were assigned on the basis of FTIR, 1H NMR, 13C NMR, mass spectral data as well as elemental analysis. In vitro antimicrobial proficiency of the title compounds were assessed against selected pathogens S. aureus MTCC 96, S. pyogeneus MTCC 442, E. coli MTCC 443 and P. aeruginosa MTCC 1688 bacteria for antibacterial activities as well as antifungal activities against C. albicans MTCC 227, A. niger MTCC 282 and A. clavatus MTCC 1323 were used. The minimum inhibitory concentration (MIC) was determined by broth dilution method and recorded at the lowest concentration inhibiting growth of the organism. Among the synthesised compounds 6b, 6c, 7b, 8b, 8d and 8e exhibited excellent antimicrobial activity and said to be the most proficient members of the series.

Anti-Mycobacterial Peroxides: A New Class of Agents for Development Against Tuberculosis

2020 ◽  
Vol 16 (3) ◽  
pp. 392-402
Author(s):  
Christiaan W. van der Westhuyzen ◽  
Richard K. Haynes ◽  
Jenny-Lee Panayides ◽  
Ian Wiid ◽  
Christopher J. Parkinson
Keyword(s):  
Subsequent Development ◽  
Antitubercular Activity ◽  
Organic Peroxide ◽  
New Drugs ◽  
Skeletal Myoblast ◽  
Artemisinin Derivatives ◽  
Malaria Therapy ◽  
New Class ◽  
Alternative Approach

Background: With few exceptions, existing tuberculosis drugs were developed many years ago and resistance profiles have emerged. This has created a need for new drugs with discrete modes of action. There is evidence that tuberculosis (like other bacteria) is susceptible to oxidative pressure and this has yet to be properly utilised as a therapeutic approach in a manner similar to that which has proven highly successful in malaria therapy. Objective: To develop an alternative approach to the incorporation of bacterial siderophores that results in the creation of antitubercular peroxidic leads for subsequent development as novel agents against tuberculosis. Methods: Eight novel peroxides were prepared and the antitubercular activity (H37Rv) was compared to existing artemisinin derivatives in vitro. The potential for toxicity was evaluated against the L6 rat skeletal myoblast and HeLa cervical cancer lines in vitro. Results: The addition of a pyrimidinyl residue to an artemisinin or, preferably, a tetraoxane peroxidic structure results in antitubercular activity in vitro. The same effect is not observed in the absence of the pyrimidine or with other heteroaromatic substituents. Conclusion: The incorporation of a pyrimidinyl residue adjacent to the peroxidic function in an organic peroxide results in anti-tubercular activity in an otherwise inactive peroxidic compound. This will be a useful approach for creating oxidative drugs to target tuberculosis.

scholarly journals Facile and Promising Method for Michael Addition of Indole and Pyrrole to Electron-Deficienttrans-β-Nitroolefins Catalyzed by a Hydrogen Bond Donor Catalyst Feist’s Acid and Preliminary Study of Antimicrobial Activity

2014 ◽  
Vol 2014 ◽  
pp. 1-15 ◽  
Author(s):  
Abdullah M. A. Al Majid ◽  
Mohammad Shahidul Islam ◽  
Assem Barakat ◽  
Mohamed H. M. Al-Agamy ◽  
Mu. Naushad
Keyword(s):  
Antimicrobial Activity ◽  
Hydrogen Bond ◽  
Michael Addition ◽  
Hydrogen Bond Donor ◽  
New Class ◽  
Optimum Reaction ◽  
Preliminary Study ◽  
Cooperative Hydrogen Bonding ◽  
The Michael Addition

The importance of cooperative hydrogen-bonding effects has been demonstrated using novel 3-methylenecyclopropane-1,2-dicarboxylic acid (Feist’s acid (FA)) as hydrogen bond donor catalysts for the addition of indole and pyrrole totrans-β-nitrostyrene derivatives. Because of the hydrogen bond donor (HBD) ability, Feist’s acid (FA) has been introduced as a new class of hydrogen bond donor catalysts for the activation of nitroolefin towards nucleophilic substitution reaction. It has effectively catalyzed the Michael addition of indoles and pyrrole toβ-nitroolefins under optimum reaction condition to furnish the corresponding Michael adducts in good to excellent yields (up to 98%). The method is general, atom-economical, convenient, and eco-friendly and could provide excellent yields and regioselectivities. Some newly synthesized compounds were for examinedin vitroantimicrobial activity and their preliminary results are reported.

scholarly journals Synthesis, Characterization, and Antimicrobial Activity of Methyl-2-aminopyridine-4-carboxylate Derivatives

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
S. Nagashree ◽  
P. Mallu ◽  
L. Mallesha ◽  
S. Bindya
Keyword(s):  
Antimicrobial Activity ◽  
Spectral Studies ◽  
H Nmr ◽  
Chemical Structures ◽  
Elemental Analyses ◽  
Ft Ir

A series of methyl-2-aminopyridine-4-carboxylate derivatives,3a–f,were synthesized in order to determine theirin vitroantimicrobial activity. The chemical structures of the synthesized compounds were confirmed by elemental analyses, FT-IR, and1H NMR spectral studies. Among the synthesized compounds,3cand3dshowed good antimicrobial activity compared to other compounds in the series.

scholarly journals Antimicrobial activity of Arctium lappa constituents against microorganisms commonly found in endodontic infections

2005 ◽  
Vol 16 (3) ◽  
pp. 192-196 ◽  
Author(s):  
Juliana Vianna Pereira ◽  
Débora Cristina Baldoqui Bergamo ◽  
José Odair Pereira ◽  
Suzelei de Castro França ◽  
Rosemeire Cristina Linhares Rodrigues Pietro ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Microbial Growth ◽  
Diffusion Method ◽  
Arctium Lappa ◽  
Retention Factors ◽  
Antimicrobial Substances ◽  
Chemical Structures ◽  
Microbial Inhibition ◽  
Endodontic Infections

This study evaluated in vitro the antimicrobial activity of rough extracts from leaves of Arctium lappa and their phases. The following microorganisms, commonly found in the oral cavity, specifically in endodontic infections, were used: Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Bacillus subtilis and Candida albicans. The agar-diffusion method allowed detection of the hexanic phase as an inhibitor of microbial growth. Bioautographic assays identified antimicrobial substances in the extract. The results showed the existence, in the rough hexanic phase and in its fractions, of constituents that have retention factors (Rf) in three distinct zones, thereby suggesting the presence of active constituents with chemical structures of different polarities that exhibited specificity against the target microorganisms. It may be concluded that the Arctium lappa constituents exhibited a great microbial inhibition potential against the tested endodontic pathogens.

scholarly journals ANTIMICROBIAL ACTIVITY STUDY OF NEW QUINAZOLIN-4(3H)-ONES AGAINST STAPHYLOCOCCUS AUREUS AND STREPTOCOCCUS PNEUMONIAE

2021 ◽  
Vol 9 (4) ◽  
pp. 318-329
Author(s):  
M. A. Samotrueva ◽  
A. A. Ozerov ◽  
A. A. Starikova ◽  
N. M. Gabitova ◽  
D. V. Merezhkina ◽  
...  
Keyword(s):  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Streptococcus Pneumoniae ◽  
Active Sites ◽  
Wide Spectrum ◽  
Experimental Studies ◽  
Amide Group ◽  
Pharmacological Effect ◽  
Dilution Method

Quinazolin-4(3H)-one derivatives exhibiting a wide spectrum of a pharmacological activity, represent a promising class of substances used to obtain antibacterial agents, which is especially important in the context of the emergence of pathogenic microorganisms’ resistance to drugs used in medicine. It has been proved that compounds having a naphthyl radical in the molecule, as well as an amide group bound to the benzene ring as quinazolinone substituents, are characterized by a pronounced antimicrobial activity against Staphylococcus aureus and Streptococcus pneumoniae.The aim of the research is a primary microbiological screening of the in vitro antimicrobial activity of new quinazolin-4(3H)-one derivatives against Staphylococcus aureus and Streptococcus pneumoniae, as well as the assessment of the relationship between the pharmacological effect and the structural transformation of the substance molecule, lipophilicity and the possibility of forming resistance to them.Materials and methods. The experimental studies have been carried out using well-known nosocomial pathogens of infectious and inflammatory diseases Staphylococcus aureus and Streptococcus pneumoniae by a serial dilution method.Results. A compound containing a naphthyl radical in its structure, which contributes to an increase in the hydrophobicity of the substance and its solubility in the membrane of a bacterial cell, has a bacteriostatic effect against both Staphylococcus aureus and Streptococcus pneumoniae. A similar pharmacological effect is exhibited by a derivative with an amide group as a substituent of the quinazolinone nucleus linked to a phenyl radical, which probably contributes to an increase in the degree of binding to active sites of enzymes involved in the DNA replication, and protein synthesis. Obviously, the increased lipophilicity, which promotes better binding to the efflux protein, cannot serve as objective characteristics of the emergence possibility of the pathogen’s resistance to this substance.Conclusion. Among the synthesized compounds, the leading substances that exhibit an antimicrobial activity against Staphylococcus aureus and Streptococcus pneumonia, have been identified. The assessment of the chemical structure made it possible to substantiate their pharmacological action and draw conclusions about the possibility of developing resistance to it in microbial cells.

scholarly journals Cytotoxic, antioxidant, and antimicrobial activities of Celery (Apium graveolens L.)

2021 ◽  
Vol 17 (1) ◽  
pp. 147-156
Author(s):  
Mohammed Saleh Al Aboody ◽  
Keyword(s):  
Antimicrobial Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Antihypertensive Agents ◽  
Apium Graveolens ◽  
Cell Protein ◽  
Dilution Method ◽  
Local Market ◽  
Antioxidant And Antimicrobial Activity

Celery (Apium graveolens Linn, Family: Apiaceae) is a common edible herb used as a spice in the traditional medicine of several nations since time immemorial. The whole plant is extensively used in cooking as soups and salads. A. graveolens has various pharmacological properties such as anticancer, anti-obesity, anti-hepatotoxic, and antihypertensive agents. Hence, it is of interest to document the in vitro cytotoxic, antioxidant, and antimicrobial activity of A. graveolens. The plants were collected in the local market, shade dried, and different parts of the plants were extracted with 70% ethanol using a cold maceration process. Antioxidant tests were performed based on the various radical scavenging methods. Antimicrobial activity and MIC were completed using the respective cup-plate and two-fold serial dilution method. In vitro cytotoxic studies were achieved by the MTT; Sulphorhodamine B assayed total cell protein content. DLA and ESC cells determined the short-term toxicity. The leaf extract exhibited significant antioxidant properties against NO, DPPH, ABTS, LPO, and HPO methods. Thus, potential inhibition against Gram-positive, Gram-negative, and fungal strains within the MIC ranges of 250-500 μg/ml was observed. All the extracts of the plant presented in the study revealed greater cytotoxicity effects against five respective cancer cell lines, L6, Vero, BRL 3A, A-549, L929, and L-929 with the ranging of 443-168.5 μg/ml. Thus, we show that A. graveolens possess a potential cytotoxic, antioxidant, and antimicrobial activity.

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME NEW 1,3,4- OXADIAZOLES, 1,2,4-TRIAZOLES AND 1,3,4-THIADIAZOLES

INDIAN DRUGS ◽  
2016 ◽  
Vol 53 (06) ◽  
pp. 18-23
Author(s):  
U. V. Laddi ◽  
◽  
S. R. Desai
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Mycobacterium Tuberculosis ◽  
Antitubercular Activity ◽  
Tuberculosis H37rv ◽  
Research Centre ◽  
Methyl Ethyl ◽  
Rhizoctonia Bataticola ◽  
Mycobacterium Tuberculosis H37rv ◽  
H37rv Strain

Some new 5-[(((α-phenyl/methyl)benzylidene)amino)oxy]methyl/ethyl-2-[4-(substituted aryl)/allyl)] amino-1,3,4-oxadiazoles (4a-p), 3-[(((α-phenyl/methyl)- benzylidene) amino)oxy]methyl/ethyl-4-(4- substitutedaryl)/allyl-5-mercapto-1,2,4-triazoles (5a-p) and 5-[(((α-phenyl/methyl)-benzylidene)amino) oxy]- methyl/ethyl-2-[4-(substituted aryl)/allyl)]amino-1,3,4-thiadiazoles (6a-p) were prepared starting from α/β-[((α-(phenyl/methyl)benzylidene)amino)oxy acetic/propionic acid hydrazides (1a-d). The structures of all the compounds have been established by elemental and spectral (IR, 1HNMR and mass) analysis. All the newly synthesised compounds have been screened for their antimicrobial activity against Escherichia coli, Bacillus cirroflagellosus, Aspergillus niger and Rhizoctonia bataticola. Some of the newly synthesised compounds have been evaluated for antituberculosis activity against Mycobacterium tuberculosis H37Rv strain by BACTEC radiometric system at Southern Research Institute, Birmingham, AL and Frederick Research Centre, Frederick, MD. Significant antimicrobial activity is observed against Escherichia coli and Rhizoctonia bataticola. A few compounds also exhibited interesting antitubercular activity against Mycobacterium tuberculosis H37Rv strain.

scholarly journals New Poly(Propylene Imine) Dendrimer Modified with Acridine and Its Cu(II) Complex: Synthesis, Characterization and Antimicrobial Activity

Materials ◽  
2019 ◽  
Vol 12 (18) ◽  
pp. 3020 ◽  
Author(s):  
Paula Bosch ◽  
Desislava Staneva ◽  
Evgenia Vasileva-Tonkova ◽  
Petar Grozdanov ◽  
Ivanka Nikolova ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Copper Ions ◽  
Spectral Characteristics ◽  
Dilution Method ◽  
Pathogenic Microorganisms ◽  
Paramagnetic Resonance ◽  
Poly Propylene ◽  
New Compounds ◽  
First Time

A second-generation poly(propylene imine) dendrimer modified with acridine and its Cu(II) complex have been synthesized for the first time. It has been found that two copper ions form complexes with the nitrogen atoms of the dendrimeric core by coordinate bonds. The new compounds have been characterized by nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), fourier-transform infrared spectroscopy (FTIR) and fluorescence spectroscopy. The spectral characteristics of the modified dendrimer have been measured in different organic solvents, and a negative fluorescence solvatochromism has been observed. The antimicrobial activity of the dendrimers has been tested against model pathogenic microorganisms in agar and by broth dilution method. The cotton fabric treated with both dendrimers has been evaluated towards pathogenic microorganisms. The obtained modified cotton fabrics have been shown to hamper bacterial growth and to prevent biofilm formation. Dendrimer cytotoxicity has been investigated in vitro in the model HEp-2 cell line.

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