3,4-Dihydropyrimidin-2(1H)-One Analogues: Microwave irradiated Synthesis with Antimicrobial and Antituberculosis Study

2019 ◽  
Vol 6 (1) ◽  
pp. 61-70
Author(s):  
Navin Patel ◽  
Sabir Pathan ◽  
Hetal I. Soni
Keyword(s):  
Microwave Irradiation ◽  
Biginelli Reaction ◽  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Chemical Diversity ◽  
Spectral Studies ◽  
Dilution Method ◽  
Bacterial Strains ◽  
Microwave Irradiation Method

Background: For rapid and sustainable synthesis, microwave irradiation method is serviceable. This present study deals with the preparation of oxadiazole and pyridine bearing 1,2,3,4- tetrahydro pyrimidine derivatives by microwave irradiation. Objective: The present study aims to carry out rapid synthesis of chloro-acetamides of oxadiazoles of Biginelli product and amino cyano derivative of pyridine by microwave-assisted heating. Our efforts are focused on the introduction of chemical diversity in the molecular framework in order to synthesize pharmacologically interesting compounds. Methods:: Microwave irradiation was used for the synthesis of 2-((3-cyano-4-(3,4-dichloro phenyl)- 6-(4-hydroxy-3-methoxyphenyl) pyridin-2-yl) amino)-N-(5-(substituted) -(6-methyl-2-oxo -1,2,3,4- tetrahydro pyrimidin-5-yl)-1,3,4-oxadiazol-2-yl)acetamide by using Biginelli reaction. New structural analogues were confirmed by spectral studies followed by their screening for in vitro antibacterial activity against Staphylococcus aureus, Staphylococcus Pyogenus, Escherichia coli and Pseudomonas aeruginosa bacterial strains and for antifungal activity against Candida albicans, Aspergillus niger and Aspergillus clavatus by micro-broth dilution method. In vitro antimycobacterial activity determined out against (Mycobacterium tuberculosis) H37Rv strain using Lowenstein-Jensen medium. Results: As compared to the conventional method, microwave irradiation method is advantageous for the synthesis of 1,2,3,4-tetrahydropyrimidin derivatives. Potent antimicrobial activities and antitubercular activity were found for some of the compounds. Conclusion: Microwave irradiation method provided an effective way to discover a novel class of antimicrobial and antituberculosis agents. 1,2,3,4-tetrahydropyrimidin derivatives showed improved antimicrobial and good antituberculosis activity.

scholarly journals Comparative studies on conventional and microwave-assisted synthesis of a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a] pyrimidines and their antimicrobial activities

2009 ◽  
Vol 7 (3) ◽  
pp. 337-342 ◽  
Author(s):  
Oztekin Algul ◽  
Asiye Meric ◽  
Serpil Polat ◽  
N. Didem Yuksek ◽  
Mehmet Serin
Keyword(s):  
Reaction Time ◽  
Microwave Irradiation ◽  
Comparative Studies ◽  
Antimicrobial Activities ◽  
Microwave Assisted Synthesis ◽  
Microwave Irradiation Method ◽  
Yield Increase ◽  
Microwave Assisted ◽  
Mic Value

AbstractComparative studies were performed on a series of 2,4-di and 2,3,4-trisubstituted benzimidazo[1,2-a]pyrimidines, which were synthesized with conventional and microwave heating methods. In microwave irradiation method, approximately, 95–97.5% of the reaction time was increased and 1–45% yield increase was obtained. All compounds were able to inhibit the growth of the screened microorganisms in vitro with MIC values between 3.9–250 μg mL−1. The highest activity was expressed by compound IIId (2,4-diphenyl-benzo[4,5]imidazo[1,2-a] pyrimidine), which has the MIC value of 3.9 μg mL−1 and 31.2 μg mL-1 for Penicillium natatum ATCC 24791 and E. faecalis ATCC 29212, respectively.

scholarly journals Synthesis, spectral studies and in vitro antimicrobial activity of some new di/tri-organotin (IV) complexes of Schiff bases derived from 2-benzoylpyridine

2017 ◽  
Vol 82 (1) ◽  
pp. 13-23 ◽  
Author(s):  
Priyanka Khatkar ◽  
Sonika Asija ◽  
Namita Singh
Keyword(s):  
Schiff Bases ◽  
Antimicrobial Agents ◽  
Lipid Membrane ◽  
Antimicrobial Activities ◽  
Molar Ratio ◽  
Spectral Studies ◽  
Dilution Method ◽  
Gram Positive ◽  
Gram Negative

In the present work, a series of twenty-four organotin (IV) complexes of the type [R2SnLCl, R3SnL] have been synthesized by the condensation of 2-benzoylpyridine Schiff bases with R2SnCl2, R3SnCl (R= Me, n-Bu, Ph) in 1:1 molar ratio. These complexes were well characterized by IR, 1H, and 13C, 119Sn NMR, XRD and mass spectral techniques. In the search for biologically more effective antimicrobial agents, all the synthesized ligands and organotin complexes were evaluated for their in vitro antimicrobial activities against two Gram positive and two Gram negative bacteria, and two fungal strains by serial dilution method. The results of spectral data revealed that the complexes formed were hexacoordinated with tridentate ligands which coordinated through azomethine N, pyridine N and carboxylate O ligation sites. The ligands on co-ordination with tin metal showed a discernible augmentation in biocidal activity, however, the Ph and Bu complexes were found to be more intoxicating. The results revealed that the synthesized complexes were more noxious towards Gram positive strains as compared to Gram negative strains which may be attributed to the presence of an outer lipid membrane of lipopolysaccharides.

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.

scholarly journals Antimicrobial Activity and Chemical Characterization of a Non-Polar Extract of Saffron Stamens in Food Matrix

Foods ◽  
2021 ◽  
Vol 10 (4) ◽  
pp. 703
Author(s):  
Severino Zara ◽  
Giacomo L. Petretto ◽  
Alberto Mannu ◽  
Giacomo Zara ◽  
Marilena Budroni ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Fatty Acid Content ◽  
Chemical Characterization ◽  
Antimicrobial Activities ◽  
Added Value ◽  
Gas Chromatography Mass Spectrometry ◽  
Food Matrix ◽  
Bacterial Strains ◽  
By Products

The production of saffron spice generates large quantities of plant by-products: over 90% of the plant material collected is discarded, and a consideration fraction of this waste is plant stamens. This work investigated the chemical composition and the antimicrobial activities of the non-polar fraction extracted from four different saffron flower stamens. The chemical composition of ethereal extracts of the saffron stamens was qualitatively assessed by means of gas–chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) analyses. These analyses revealed ethereal extracts to possess a high polyunsaturated fatty acid content. In vitro antibacterial activity of stamen extracts showed no large differences between Gram-positive and Gram-negative bacteria in terms of minimal inhibitory concentration (MIC). In food matrix microbial analysis of the bacterial strains belonging to the main foodborne pathogen species, including Staphylococcus aureus DSM 20231, Escherichia coli DSM 30083, and Listeria monocytogenes DSM 20600, using low-fat UHT milk, revealed a statistically significant reduction in the number of cells (particularly for E. coli and S. aureus with a complete elimination of the population of the two target bacteria following incubation in diethyl ether extracts of saffron stamen (DES) at high concentrations tested, both at 37 °C and 6 °C (for 48 h and 7 days, respectively). A synergic effect was observed when the pathogens were incubated at 6 °C with DES. This work shows these by-products to be excellent sources of bioactive compounds, which could be exploited in high-added-value products, such as food, cosmetics, and drugs.

scholarly journals Symbiotic NCR Peptide Fragments Affect the Viability, Morphology and Biofilm Formation of Candida Species

2021 ◽  
Vol 22 (7) ◽  
pp. 3666
Author(s):  
Bettina Szerencsés ◽  
Attila Gácser ◽  
Gabriella Endre ◽  
Ildikó Domonkos ◽  
Hilda Tiricz ◽  
...  
Keyword(s):  
Candida Species ◽  
Biofilm Formation ◽  
Therapeutic Potential ◽  
Fungal Infections ◽  
Combined Treatment ◽  
Antimicrobial Activities ◽  
Dilution Method ◽  
Model Legume ◽  
Anticandidal Activity

The increasing rate of fungal infections causes global problems not only in human healthcare but agriculture as well. To combat fungal pathogens limited numbers of antifungal agents are available therefore alternative drugs are needed. Antimicrobial peptides are potent candidates because of their broad activity spectrum and their diverse mode of actions. The model legume Medicago truncatula produces >700 nodule specific cysteine-rich (NCR) peptides in symbiosis and many of them have in vitro antimicrobial activities without considerable toxicity on human cells. In this work we demonstrate the anticandidal activity of the NCR335 and NCR169 peptide derivatives against five Candida species by using the micro-dilution method, measuring inhibition of biofilm formation with the XTT (2,3-Bis-(2-Methoxy-4-Nitro-5-Sulfophenyl)-2H-Tetrazolium-5-Carboxanilide) assay, and assessing the morphological change of dimorphic Candida species by microscopy. We show that both the N- and C-terminal regions of NCR335 possess anticandidal activity as well as the C-terminal sequence of NCR169. The active peptides inhibit biofilm formation and the yeast-hypha transformation. Combined treatment of C. auris with peptides and fluconazole revealed synergistic interactions and reduced 2-8-fold the minimal inhibitory concentrations. Our results demonstrate that shortening NCR peptides can even enhance and broaden their anticandidal activity and therapeutic potential.

scholarly journals Synthesis and Biological Evaluation of Aminonaphthols Incorporated Indole Derivatives

2014 ◽  
Vol 2014 ◽  
pp. 1-12 ◽  
Author(s):  
Saundane Anand Raghunath ◽  
Kirankumar Nandibeoor Mathada
Keyword(s):  
Radical Scavenging ◽  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Biological Evaluation ◽  
Secondary Amines ◽  
Anticancer Activities ◽  
One Pot ◽  
Antioxidant Power ◽  
Mic Value

An efficient one pot condensation of naphthols (1), 2,5-disubstituted indole-3-carboxaldehydes (2), and secondary amines (3) has been achieved using dichloromethane as a solvent, stirring at room temperature. Some of the new [(disubstituted amino)(5-substituted 2-phenyl-1H-indol-3-yl)methyl]naphthalene-ols (4) derivatives were prepared in good yields. The significant features of this method are simple work-up procedure, inexpensive nontoxic solvent, shorter reaction times, and excellent product yields. The structures of newly synthesized compounds (4a–r) are confirmed by their elemental analysis, FTIR, 1H and 13C NMR, and mass spectral data. These compounds were screened for their in vitro antioxidant, antimicrobial, antitubercular, and anticancer activities. Among the synthesized compounds (4a–r), the compound 4e exhibited highest activity for radical scavenging and ferric ions reducing antioxidant power activities; compounds 4b, 4h, and 4k showed good metal chelating activity. Compounds 4n and 4q showed excellent antimicrobial activities with MIC value 08 µg/mL against tested strains. Compounds 4h, 4k, 4n, and 4q exhibited promising antitubercular activity with MIC value 12.5 µg/mL. Compounds 4k and 4q exhibited 100% cell lysis at concentration 10 µg/mL against MDA-MB-231 (human adenocarcinoma mammary gland) cell lines.

scholarly journals The PHYTOCHEMICALS, ANTIOXIDANT AND ANTIMICROBIAL PROPERTIES OF Senna alata AND Senna tora LEAF EXTRACTS AGAINST BACTERIAL STRAINS CAUSING SKIN INFECTIONS

2019 ◽  
Vol 2 (1) ◽  
pp. 19
Author(s):  
Murni Halim
Keyword(s):  
Leaf Extract ◽  
Antimicrobial Properties ◽  
Inhibition Zone ◽  
Antimicrobial Activities ◽  
Diffusion Method ◽  
Bacterial Strains ◽  
Leaf Extracts ◽  
Natural Drugs ◽  
Senna Alata

A study was carried out to screen for phytochemical constituents and assess the antioxidant and antimicrobial activities of Senna alata and Senna tora leaf extracts. The leaves were first dried at room temperature and 50°C in an oven prior to solvent extraction using ethanol and methanol. The in-vitro qualitative assays showed that both S. alata and S. tora leaf extracts contained bioactive and secondary metabolites components such as tannins, steroids, saponin, terpenoids, glycosides, flavonoids and phenols. The antioxidant activity and capacity test were carried out by conducting free radical of 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging activity and Ferric reduction antioxidant plasma (FRAP) assays. Both assays showed S. tora leaf extract has higher antioxidant capacity than S. alata leaf extract. The efficacy of these leaf extracts were tested against skin pathogens through agar well diffusion method. S. alata extract showed an inhibition zone (1.15 – 1.59 mm) against Pseudomonas aeruginosa while S. tora extracts exhibited a strong antimicrobial activity against S. epidermidis (inhibition zone of 12 – 16.94 mm) followed by P. aeruginosa (inhibition zone of 1 – 1.59 mm). Nonetheless, no inhibition zone was observed for S. aureus by both leaf extracts. The phytochemicals and antioxidant constituents as well as inhibitory potential on skin pathogens possessed by S. alata and S. tora leave highlighted their potential utilization in the development of natural drugs or cosmetics to treat skin related diseases or infections.

scholarly journals SYNTHESIS, SPECTRAL CHARACTERIZATION AND ANTIMICROBIAL ACTIVITIES OF BIS(CYCLOPENTADIENYL)TITANIUM(IV) COMPLEXES WITH SCHIFF BASES DERIVED FROM5-(SUBSTITUTED ARYL)-2-HYDRAZINO-1, 3, 4-OXADIAZOLE AND INDOLINE-2, 3-DIONE

2021 ◽  
Vol 9 (09) ◽  
pp. 900-909
Author(s):  
Anupama Srivastava ◽  
◽  
Shilpi Srivastava ◽  
Om. P. Pandey ◽  
Soumitra K. Sengupta ◽  
...  
Keyword(s):  
Schiff Bases ◽  
Electrical Conductance ◽  
Antimicrobial Effect ◽  
Antimicrobial Activities ◽  
Molar Conductance ◽  
Bacterial Strains ◽  
Monoclinic Crystal ◽  
Spectral Techniques ◽  
Concentration Method

Titanium(IV) complexes of type[(η5-C5H5)2TiCl(L)] have been synthesized by the reactions of bis(cyclopentadienyl)titanium(IV)dichloride with Schiff bases (LH) derived by the condensation of 5-(substituted aryl)-2-hydrazino-1,3,4-oxadiazole and indoline-2,3-dione in tetrahydrofuranin the presence oftriethylamine. All these complexes are soluble in PhNO2, DMF and DMSO.The complexes were characterized by elemental analyses, electrical conductance, magnetic susceptibility, UV-Vis, IR, 1H NMR, 13C NMR, XRD and SEM spectral techniques. Low molar conductance values indicate that they are non-electrolytes. The spectral data indicate5-coordinate geometry for the complexes.XRD pattern indicate that the complexes have monoclinic crystal system and particle sizes were found 49.36 nm (nano-size). In vitro antifungal activity of synthesized compounds was evaluated against fungi Aspergillusniger, Aspergillusflavus,ColletotrichumfalcatumandIn vitro antibacterial activity was determined by screening the compounds against gram negative (P. aeruginosa, S.typhi) and gram positive (S. aureus and B.subtilis) bacterial strains using minimum inhibition concentration method (MIC) by serial dilution technique. The titanocene(IV) complexes have higher antimicrobial effect than the parent Schiff bases.

scholarly journals Synthesis,Characterization and Evaluation of the Anticancer and Antimicrobial Activities of Some Novel Benzazole and Benzazine Derivatives

2007 ◽  
Vol 3 (3) ◽  
pp. 252-263
Author(s):  
Wesam Saber Shehab ◽  
Naglaa Z.H. Eleiwa ◽  
Samar.M. Mouneir
Keyword(s):  
Cancer Cells ◽  
Benzimidazole Derivative ◽  
Coupling Reaction ◽  
Antimicrobial Activities ◽  
Spectral Studies ◽  
Design Modification ◽  
Future Design ◽  
Antibacterial And Antifungal Activities ◽  
Antibacterial And Antifungal

The present study was designed to synthesize  and develop new useful lead compounds (some novel benzazole and benzazine derivatives ) of simple structure , exhibiting optimal in vitro anticancer  and antimicrobial potency. Phenylenediamine derivative 1 was condensed  with  dithiocarboxylic acid derivatives 2 and produced   benzimidazole derivative 4. The benzotriazepines 8 and 10  were formed by the reaction of 1 with dicarbonyl derivatives followed by intermolecular coupling reaction. The synthesis of benzotriazine12, benzotriazole 14,17, benzimidazole16 and benzothiadiazine 19 from compound 1 was also described. The Synthesized Compounds were characterized by Spectral Studies like IR, H1 – NMR and Analysis Spectra .The title compounds were screened for their possible In vitro anticancer and antimicrobial activities. Among the synthesized compounds, some have shown promisingly remarkable activities against  different  cancer cell lines (MCF-7 human breast cancer cells, HepG2 human hepatocarcinoma cells and PC3 human prostate cancer cells)and moderate  to high antibacterial and antifungal activities. The obtained results showed that the most active compounds could be useful as a template for future design, modification and investigation to produce more active analogs.

Ginseng aqueous extract attenuates the production of virulence factors, stimulates twitching and adhesion, and eradicates biofilms of Pseudomonas aeruginosa

2011 ◽  
Vol 89 (6) ◽  
pp. 419-427 ◽  
Author(s):  
Misagh Alipour ◽  
Abdelwahab Omri ◽  
Zacharias E. Suntres
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Virulence Factors ◽  
Aqueous Extract ◽  
North American ◽  
American Ginseng ◽  
Antimicrobial Activities ◽  
Live Cells ◽  
Dilution Method ◽  
Agar Dilution Method

This study was carried out to examine the antimicrobial activity of the aqueous extract of Panax quinquefolius from North American ginseng (NAGE) root against Pseudomonas aeruginosa . The minimum inhibitory concentrations of reference and clinical isolates of Pseudomonas aeruginosa were measured by a standard agar-dilution method. At subinhibitory NAGE concentrations, the secretion of virulence factors, motility on agar, and adhesion to 96-well microplates were studied on the nonmucoid Pseudomonas aeruginosa O1 strain. At suprainhibitory concentrations, the activity of NAGE against mature biofilm complexes formed in the Calgary Biofilm Device and the Stovall flow cell were assessed. NAGE possessed an antibacterial activity against all the Pseudomonas aeruginosa strains at 1.25%–2.5% w/v. NAGE also significantly attenuated pyocyanin, pyoverdine, and lipase concentrations, stimulated twitching, and attenuated swarming and swimming motility. At 1.25% w/v, NAGE augmented adhesion, and at 5% w/v detached 1-day-old biofilms in microplates. The extract also eradicated 6-day-old mature biofilms (5% w/v), and fluorescence microscopy displayed a reduction of live cells and biofilm complexes compared with nontreated biofilms. These data suggest that the aqueous extract from North American ginseng possesses antimicrobial activities in vitro.

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