scholarly journals Synthesis and Antimicrobial, Antiproliferative Evaluation of Novel Quinolone and Conazole Analogues via Conventional and Microwave Techniques

2021 ◽  
Author(s):  
Şule Ceylan ◽  
Yıldız Uygun Cebeci ◽  
Neslihan Demirbaş ◽  
Şengül Alpay Karaoğlu ◽  
Muhammed Altun
Keyword(s):  
Antitubercular Activity ◽  
Antimicrobial Activities ◽  
Mannich Bases ◽  
Ring Closure ◽  
Anticancer Activities ◽  
Standard Drug ◽  
Antiproliferative Effects ◽  
Benzyl Chlorides ◽  
Cervical Cancer Cells ◽  
Microwave Techniques

Abstract 1,2,4-Triazole-3-one (3), acquired from cinnemaldehyde was converted to the corresponding carbox(thio)amides via several steps (6a-c). Their reaction with sodium hydroxide gave the 1,2,4-triazole derivatives (7a-c). Compound 3 treatment with 2-bromo-1-(4-chlorophenyl) ethanone or 2-chloro-1-(2,4-dichlorophenyl)ethanone afforded the compounds 8a,b and by reducing these compounds reduction products were obtained (9a,b). The synthesis of (10a-e) was carried out by the reaction compounds 9a,b with different benzyl chlorides. Then oxadiazol derivative (12) was obtained by ring closure from hydrazide compound 5. Subsequently compounds 3, 7a-c and 12 were treated with various amines in the presence of formaldehyde to yield Mannich bases (11a-e, 14a-e, 13a,b). Microwave-assisted and conventional techniques were utilized for the syntheses. The structures of newly synthesized compounds were illuminated by spectroscopic methods. Their antimicrobial (MIC method), and anticancer activities (Abay’s method) were examined. Results showed that most of the compounds exhibited good antimicrobial activities. Especially compounds 14a-e which is a mannich base showed very good antitubercular activity against Mycobacterium smegmatis compared with Streptomycin standard drug. Also compounds 8a and 9b have been found to have strong antiproliferative effects on the HeLa cervical cancer cells and also these compounds did not have cytotoxic effect on normal cell.

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 ANTI CANCER STUDIES OF SELECTIVE MANNICH BASES BY IN SILICO METHOD

2018 ◽  
Vol 10 (2) ◽  
pp. 81 ◽  
Author(s):  
L. Muruganandam ◽  
Maheswari R.
Keyword(s):  
Estrogen Receptor ◽  
In Silico ◽  
Mannich Bases ◽  
Receptor Protein ◽  
Crystallographic Structure ◽  
Anticancer Activities ◽  
Standard Drug ◽  
Estrogen Receptor Protein ◽  
Discovery Studio

Objective: To evaluate the anticancer activities of selective Mannich bases by in silico methods.Methods: X-ray crystallographic structure of Estrogen receptor protein (PDB ID 2YAT) was downloaded from the protein data bank (PDB) and is docked with the target Mannich bases using Accelyrs Discovery Studio client version 2.5 software.Results: Based on the in silico analysis results of the target compounds with standard drug tamoxifen, the best-docked compound is identified and its anticancer activity is confirmed by using in vitro MTS analysis using Raju and Jurkat cell lines.Conclusion: The mannich base compound N-[(Diphenylamino) methyl] acetamide showed fourfold higher activity than standard drug tamoxifen, may be used to overcome the drug resistance of Estrogen receptor protein.

scholarly journals Facile syntheses of Mannich bases of 3-[p-(5'-aryl-pyrazolin-3'-yl)]-phenylsydnones, as anti-tubercular and anti-microbial agents, under ionic liquid/TBAB catalytic conditions

2011 ◽  
Vol 76 (8) ◽  
pp. 1069-1079 ◽  
Author(s):  
Tasneem Taj ◽  
Ravindra Kamble ◽  
T.M. Gireesh ◽  
Ravindra Hunnur
Keyword(s):  
Ionic Liquid ◽  
Ionic Liquids ◽  
Antitubercular Activity ◽  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
Mannich Bases ◽  
Secondary Amines ◽  
1H And 13C Nmr ◽  
Microbial Agents ◽  
Pyrazoline Derivative

% MIC % antitubercular activity KR nema Novel methylene bridged Mannich bases 2(a-j) were synthesized in good to excellent yields from the pyrazoline derivative (1) using various primary/secondary amines, 37 % formalin in presence of ionic liquids/TBas catalyst. The structures of the newly synthesized compounds were confirmed by IR, 1H- and 13C-NMR and GC-MS spectroscopy, as well as elemental analysis. The title compounds were screened for their anti-tubercular and antimicrobial activities. Some of the compounds exhibited very good anti-tubercular, antifungal and antibacterial activities.

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 In Vitro Assessment of Antioxidant, Thrombolytic, Antimicrobial Activities of Medicinal Plant Pandanus odoratissimus L. Leaves Extract

2020 ◽  
Vol 12 (3) ◽  
pp. 379-390
Author(s):  
F. I. Penu ◽  
S. M. Ivy ◽  
F. Ahmed ◽  
J. Uddin ◽  
M. S. Hossain ◽  
...  
Keyword(s):  
Soluble Fraction ◽  
Blood Clot ◽  
Folk Medicine ◽  
Maximum Level ◽  
Antimicrobial Activities ◽  
Total Phenolic ◽  
Thrombolytic Activity ◽  
Standard Drug ◽  
Pandanus Odoratissimus

The present study was carried out to investigate phytochemical, antioxidant; antimicrobial, thrombolytic activity and estimate total phenolic, total flavonoid content of Pandanus odoratissimus (p.odoratissimus) leaves of methanol extract. In thrombolytic activity, aqueous soluble fraction (AQSF) exhibited highest percentage (46.58 %) of potential to lyse blood clot compared to standard drug streptokinase (69.52 %). In antimicrobial assay, dichloromethane soluble fraction (DCMSF) explored the highest diameter of clear zone of inhibition against both gram positive (19.60 ± 0.12 mm) and gram negative (20.00 ± 0.20 mm) bacteria compared to standard antibiotic, Kanamycin (50.00 ± 0.19). Levels of antioxidant were determined by DPPH assay followed by calculated IC50 values of different Kupchan extracts. The methyl soluble fraction (MSF) showed the lowest level of IC50 value (36.70 ± 0.32 µg/mL) in comparison to ascorbic acid (12.48 ± 0.09 µg/mL) while MSF disclosed the maximum level (62.19 ±  0.26 mg of GAE/g of extract) of total phenolic content in the extracts of P. odoratissimus. This study was conducted to validate the P. odoratissimus leaves used as a folk medicine such as, antioxidant, thrombolytic, and antimicrobial potential.

SYNTHESIS AND EVALUATION OF SOME SUBSTITUTED 2-AMINOTHIAZOLE DERIVATIVES FOR THEIR ANTITUBERCULAR, ANTIMICROBIAL & ANTIFUNGAL ACTIVITY

INDIAN DRUGS ◽  
2012 ◽  
Vol 49 (01) ◽  
pp. 24-32
Author(s):  
S. R. Pattan ◽  
◽  
S. H Kale ◽  
R. A. Mali ◽  
S. S. Dengale ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Antitubercular Activity ◽  
Diffusion Method ◽  
Zone Of Inhibition ◽  
Standard Drug ◽  
E Coli ◽  
H Nmr ◽  
Antimicrobial And Antifungal Activity ◽  
Micro Organisms

Millions of people are affected by infectious diseases caused by micro-organisms. Further the widespread microbial resistance had renewed the interest in quest for new antitubercular, antimicrobial & antifungal agents. The present study deals with synthesis & evaluation of some substituted 2-aminothiazole derivatives for their antitubercular, antimicrobial and antifungal activity. 2-aminothiazole derivatives were synthesized by treating substituted acetophenones with thiourea in presence of bromine to give 2-amino 4-substituted phenylthizole and then further treated with chloracetyl chloride to give 2-chloro-N-(4-substituted phenylthizole-2-yl)-acetamide which on refluxing with primary amine gives 15 derivatives. All the synthesized compounds were characterized by IR, H-NMR and elemental analysis.All the synthesized compounds were screened for their antibacterial activity against S. aureus and E. coli by using cup plate agar diffusion method. The activity was measured in terms of zone of inhibition and compared with standard drug ciprofloxacin, sulfonamide. The aminothiazole derivatives were evaluated for antitubercular activity and their result were compared with standard streptomycin.

scholarly journals Synthesis, Characterization & Antimicrobial Activities of New Isoxazole Substituted Mannich and Schiff Bases of 5-Nitroisatin Analogs

2020 ◽  
Vol 32 (4) ◽  
pp. 970-974
Author(s):  
Ch. Jithendra ◽  
G. Saravanan ◽  
V. Alagarsamy ◽  
T. Panneerselvam ◽  
K. Selvaraj ◽  
...  
Keyword(s):  
Biological Activity ◽  
Functional Group ◽  
Mannich Base ◽  
Antimicrobial Activities ◽  
Mannich Bases ◽  
Pathogenic Microorganism ◽  
Diffusion Technique ◽  
Group Variation ◽  
The Relationship ◽  
Isoxazole Derivatives

A sequence of new isoxazole substituted Schiff base and Mannich base of 5-nitroisatin are synthesized by a multi-step synthesis from 5-nitroisatin. Whole synthesized analogs were characterized using IR, NMR, Mass spectroscopy and microanalyses. All the Schiff and Mannich bases were tested for their antimicrobial potencies against some human pathogenic microorganism using agar well diffusion technique. The relationship between the biological activity and the functional group variation of the Schiff and Mannich bases were analyzed. Standard ciprofloxacin and ketoconazole were used to compare the antimicrobial activities of novel isatin coupled isoxazole derivatives.

scholarly journals Phenolic Composition of Leaf extracts of Ailanthus altissima (Simaroubaceae) with Antibacterial and Antifungal Activity Equivalent to Standard Antibiotics

2017 ◽  
Vol 12 (10) ◽  
pp. 1934578X1701201 ◽  
Author(s):  
Danijela Poljuha ◽  
Barbara Sladonja ◽  
Ivana Šola ◽  
Slavica Dudaš ◽  
Josipa Bilić ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
Antimicrobial Activities ◽  
Positive Control ◽  
Ailanthus Altissima ◽  
Phenolic Composition ◽  
Mechanical Wounding ◽  
Leaf Extracts ◽  
Standard Drug ◽  
Pharmaceutical Application ◽  
Before And After

Extracts of fresh and dry Ailanthus altissima leaves from Croatia were evaluated for their phenolic composition, antioxidant and antimicrobial activities. The methanolic extract had a higher concentration of total phenolics, flavonoids and non-flavonoids, as well as a higher antioxidant capacity than water extracts. Flavonoids identified in A. altissima leaves belong to two groups: flavones (glycosides of apigenin and luteolin) and flavonols (glycosides of quercetin and kaempferol). They were mainly present as glycosides, quercetin-3- O-glucoside was the predominant flavonoid. Only traces of aglycones were detected even after extract hydrolysis. Caffeic acid was the predominant phenolic acid both before and after hydrolysis, followed by chlorogenic acid after hydrolysis. The concentration of chlorogenic acid significantly increased soon after tissue fragmentation suggesting this compound is involved in rapid response against mechanical wounding in A. altissima. Therefore, to increase the chlorogenic acid concentration, mechanical wounding could be applied. The acetone leaf extract was as active against Escherichia coli as the positive control gentamicin. Both acetone and methanol:dichloromethane extracts had a higher activity against Candida albicans than a standard drug amphotericin B. Therefore, A. altissima could serve as a valuable resource for antimicrobial activity, which makes this species interesting for further investigation and possible pharmaceutical application.

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.

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