Synthesis, Characterization, and Biological Activity of Novel Schiff and Mannich Bases of 4-Amino-3-(N-phthalimidomethyl)-1,2,4-triazole-5-thione

The present work describes the syntheses and antimicrobial activity studies of a series of novel Schiff bases (4a–4i) and their Mannich bases (5a–5h) starting from 4-amino-3-(N-phthalimido-methyl)-1,2,4-triazole-5-thione (3). All the synthesized compounds were characterized by IR,1H-NMR,13C-NMR, and MS. All the synthesized compounds were screened for four Gram-negative strains, one Gram-positive strain of bacteria, and one diploid fungal strain. In general the antimicrobial activity increased remarkably on the introduction of azomethine functionality in parent triazole (3). The antimicrobial activity further improved when morpholine group was added to them except forEnterobacter cloacae, where loss of activity was observed. The results are promising and show that the fine tuning of the structures (5a, 5b, 5e, 5f,and5h) can lead to some new antimicrobial compounds.

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Synthesis and Antimicrobial Activity of Some New Imidazolinone Derivatives Containing Benzimidazole

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.29.74 ◽

2014 ◽

Vol 29 ◽

pp. 74-80

Author(s):

Prakash Mehta ◽

Prakash Davadra ◽

Nirav Shah ◽

Hitendra Joshi

Keyword(s):

Antimicrobial Activity ◽

Hippuric Acid ◽

Fungal Strain ◽

Gram Negative Bacteria ◽

Good Activity ◽

Standard Drug ◽

Gram Negative ◽

H Nmr ◽

Target Molecules ◽

Carbohydrazide Derivative

In this study some new o-benzimidazol-2'-yl-benzamido-p'-benzamido-2-phenyl-4-substituted phenyl-5-oxo-Imidazolines 3a-3j were synthesized. To synthesized target molecules we used various substituted oxazolone derivatives, synthesized from substituted benzaldehyde with hippuric acid. Substituted oxazolones 2a-2j were reacted with carbohydrazide derivative of benzimidazole 1 in presence of pyridine as base to obtained substituted imidazolinone derivatives. All synthesized compounds were characterized by IR, 1H NMR, elemental analysis and further supported by mass spectroscopy. All synthesized compounds were screened for their antimicrobial activity against gram positive and gram negative bacteria which showed moderate to good activity. All compounds showing good to moderate active against fungal strain as compare to standard drug.

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Synthesis and Antimicrobial Activity of Some New Thiazolidin-4-one Derivatives of 4-(6-methylbenzo[d]thiazol-2-yl)benzamine

Journal of Chemistry ◽

10.1155/2013/185952 ◽

2013 ◽

Vol 2013 ◽

pp. 1-6

Author(s):

Awaz Jamil Hussein ◽

Hashim Jalal Azeez

Keyword(s):

Escherichia Coli ◽

Antimicrobial Activity ◽

Significant Activity ◽

Gram Negative ◽

H Nmr ◽

Cyclocondensation Reaction ◽

Ft Ir ◽

High Yields ◽

Derivatives Of ◽

C Nmr

A number of derivatives of 2-(substituted phenyl)-3-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl) thiazolidin-4-one (3a–j) have been synthesized from the reaction of 4-(6-methylbenzo[d]thiazol-2-yl)benzenamine(1), with different substituted benzaldehydes (2a–j), followed by cyclocondensation reaction of the prepared imines with 2-meraptoacetic acid in high yields. Furthermore, the structures of the newly synthesized compounds were confirmed by FT-IR,13C-NMR,13C-DEPT, and1H-NMR spectral data. The imines and thiazolidin-4-one derivatives were evaluated for their antibacterial activity againstEscherichia colias gram negative andStaphylococcus aureusas gram positive, the results have shown significant activity against both types of bacteria.

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Synthesis, Characterization and Antimicrobial Activity of some New Dihydropyrano[c] Chromenes

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.31.1 ◽

2014 ◽

Vol 31 ◽

pp. 1-6

Author(s):

Ankita A. Bhalu ◽

Pooja Moteriya ◽

Sumitra Chanda ◽

Shipra H. Baluja

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Ir Spectroscopy ◽

Fungal Strain ◽

Bacterial Strains ◽

Gram Positive ◽

Gram Negative ◽

Antimicrobial Screening ◽

Fungal Strains ◽

H Nmr

Some new dihydropyrano[c]chromenes derivatives are synthesized from 4-hydroxycoumarin. The structure of newly synthesized compounds was confirmed by mass, 1H NMR and IR spectroscopy. Further, antimicrobial screening of these synthesized compounds was done against some bacterial (Gram positive as well as Gram negative) and fungal strains in N,N-dimethylformamide. It is observed that some of synthesized compounds exhibited significant antibacterial activity against Gram positive bacterial strains. The selected fungal strains were most resistant for the studied compounds as none of the synthesized compounds showed activity against any of the fungal strain studied. The best antibacterial activity was shown by ABR-10.

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Synthesis and Antimicrobial Activity of Coumarinyl Schiff Base Derivatives

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.30.193 ◽

2014 ◽

Vol 30 ◽

pp. 193-201 ◽

Cited By ~ 2

Author(s):

Arun Mishra ◽

Jaynt Rathod ◽

Dipti Namera ◽

Shailesh Thakrar ◽

Anamik Shah

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antimicrobial Activity ◽

Gram Negative ◽

H Nmr ◽

Schiff Base Derivatives ◽

Test Organisms ◽

Ft Ir ◽

C Nmr

We have reported some novel N’-[(1)-ethylidene]-2-(6-methyl-2-oxo-2H-chromen-4-yl) acetohydrazide synthesized by conventional method. The reaction of 2-(6-methyl-2-oxo-2H-chromen-4-yl)acetohydrazide with substituted benzaldehyde in methanol as a solvent yielded a series of (7a-l). The structures of all synthesized compounds are well characterized by Mass, FT-IR, 1H NMR, 13C NMR and elemental analysis. Moreover, all synthesized compounds were screened for In Vitro antimicrobial activity against the gram positive (Staphylococcus aureus, Bacilluas subtilis) and gram negative (Escherichia coli, P. aeruginosa, K. pneunonae, Enterobacter) bacterial strain. In which some the compounds show potential inhibition against the test organisms.

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SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF 3-FORMYL INDOLE BASED SCHIFF BASES

Journal of Biomedical and Pharmaceutical Research ◽

10.32553/jbpr.v7i6.561 ◽

2018 ◽

Vol 7 (6) ◽

Author(s):

Singh Gurvinder ◽

Singh Prabhsimran ◽

Dhawan R. K.

Keyword(s):

Antimicrobial Activity ◽

Spectral Analysis ◽

Schiff Bases ◽

Antimicrobial Agents ◽

Biological Evaluation ◽

Fungal Strain ◽

Bacterial Strains ◽

Standard Drug ◽

Gram Negative ◽

E Coli

In order to develop new antimicrobial agents, a series of 3-formyl indole based Schiff bases were synthesized by reacting 3-formyl indole(indole-3-carboxaldehyde) with substituted aniline taking ethanol as solvent. The reaction was carried in the presence of small amount of p-toluene sulphonic acid as catalyst.All the synthesized compounds were characterized by IR, 1H-NMR spectral analysis. All the synthesized compounds were evaluated for antimicrobial activity against two gram positive bacterial strains (B. subtilisand S. aureus) and two gram negative bacterial strains (P. aeruginosaand E. coli) and one fungal strain (C. albicans). All the synthesized compounds were found to have moderate to good antimicrobial activity. The standard drug amoxicillin, fluconazole were used for antimicrobial activity. Among the synthesized compounds, the maximum antimicrobial activity was shown by compounds GS04, GS07, GS08 and GS10.

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SYNTHESIS AND STRUCTURAL ELUCIDATION OF AMINO ACETYLENIC AND THIOCARBAMATES DERIVATIVES FOR 2-MERCAPTOBENZOTHIAZOLE AS ANTIMICROBIAL AGENTS

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2017v9i2.15760 ◽

2017 ◽

Vol 9 (2) ◽

pp. 192

Author(s):

Aseel Alsarahni ◽

Zuhair Muhi Eldeen ◽

Elham Al-kaissi ◽

Ibrahim Al- Adham ◽

Najah Al-muhtaseb

Keyword(s):

Antimicrobial Activity ◽

Elemental Analysis ◽

Antimicrobial Agents ◽

Diffusion Method ◽

Benzothiazole Derivatives ◽

H Nmr ◽

Ft Ir ◽

Potential Antimicrobial Activity ◽

C Nmr

Objective: To design and synthesize amino acetylenic and thiocarbonate of 2-mercapto-1,3-benthiazoles as potential antimicrobial agents.Methods: A new series of 2-{[4-(t-amino-1-yl) but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole derivatives (AZ1-AZ6), and S-1,3-benzothiazol-2-yl-O-alkyl carbonothioate derivatives were synthesised, with the aim that the target compounds show new and potential antimicrobial activity. The elemental analysis was indicated by the EuroEA elemental analyzer, and biological characterization was via IR, 1H-NMR, [13]C-NMR, DSC were determined with the aid of Bruker FT-IR and Varian 300 MHz spectrometer using DMSO-d6 as a solvent. In vitro antimicrobial activity, evaluation was done for the synthesised compounds, by agar diffusion method and broth dilution test. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were determined. Results: The IR, 1H-NMR, 13C-NMR, DSC and elemental analysis were consistent with the assigned structures. Compound of 2-{[4-(4-methylpiperazin-1-yl)but-2-yn-1-yl] sulfanyl}-1,3-benzothiazole (AZ1), 2-{[4-(2-methylpiperidin-1-yl)but-2-yn-1-yl]sulfanyl}-1,3-benzothiazole (AZ2), 2-{[4-(piperidin-1-yl) but-2-yn-1-yl]sulfanyl}-1, 3-benzothiazole (AZ6), S-1,3-benzothiazol-2-yl-O-ethyl carbonothioate (AZ7), and S-1,3-benzothiazol-2-yl-O-(2-methylpropyl) carbonothioate (AZ9) showed the highest antimicrobial activity against Pseudomonas aeruginosa (P. aeruginosa), AZ-9 demonstrated the highest antifungal activity against Candida albicans (C. albicans), with MIC of 31.25 µg/ml.Conclusion: These promising results promoted our interest to investigate other structural analogues for their antimicrobial activity further.

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Correlation between the Antimicrobial Activity and Metabolic Profiles of Cell Free Supernatants and Membrane Vesicles Produced by Lactobacillus reuteri DSM 17938

Microorganisms ◽

10.3390/microorganisms8111653 ◽

2020 ◽

Vol 8 (11) ◽

pp. 1653

Author(s):

Alessandro Maccelli ◽

Simone Carradori ◽

Valentina Puca ◽

Francesca Sisto ◽

Paola Lanuti ◽

...

Keyword(s):

Antimicrobial Activity ◽

Lactobacillus Reuteri ◽

Membrane Vesicles ◽

Metabolic Profiles ◽

Ion Cyclotron Resonance ◽

Antimicrobial Compounds ◽

Ionization Source ◽

Gram Positive ◽

Gram Negative ◽

Broth Microdilution Method

The aim of the work is to assess the antimicrobial activities of Cell Free Supernatants (CFS) and Membrane Vesicles (MVs), produced by Lactobacillus reuteri DSM 17938, versus Gram-positive and Gram-negative bacteria and investigate their metabolic profiles. The Minimum Inhibitory Concentration was determined through the broth microdilution method and cell proliferation assay while the Minimum Bactericidal Concentration was determined by Colony Forming Units counts. The characteristics of the antimicrobial compounds were evaluated by pH adjustments, proteinase treatment, and size fractionation of the CFS. The cytotoxicity of CFS was tested on two human cell lines. A detailed snapshot of the L. reuteri metabolism was attained through an untargeted metabolic profiling by means of high resolution Fourier Transform Ion Cyclotron Resonance Mass Spectrometry (FT-ICR MS) coupled with Electrospray Ionization Source (ESI). The results showed (i) a greater efficacy of CFS and its fractions towards Gram-negative compared to Gram-positive bacteria; (ii) an antimicrobial effect related to pH-dependent compounds but not to MVs; (iii) a molecular weight < 3 KDa as well as an a non-proteinaceous nature of the antimicrobial compounds; and (iv) more than 200 and 500 putative metabolites annotated in MVs and supernatants, covering several classes of metabolites, including amino acids, lipids, fatty and organic acids, polyalcohols, nucleotides, and vitamins. Some putative compounds were proposed not only as characteristic of specific fractions, but also possibly involved in antimicrobial activity.

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Approach for the Synthesis of Potent Antimicrobials Containing Pyrazole, Pyrimidine and Morpholine Analogues

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.69.87 ◽

2016 ◽

Vol 69 ◽

pp. 87-96 ◽

Cited By ~ 1

Author(s):

Nisheeth C. Desai ◽

Bonny Y. Patel ◽

Bharti P. Dave

Keyword(s):

Antimicrobial Activity ◽

Dilution Method ◽

Mass Spectral ◽

H Nmr ◽

Sar Studies ◽

Mueller Hinton ◽

Morpholine Derivatives ◽

Mueller Hinton Broth ◽

C Nmr

The present study is in the interest of some synthesized novel derivatives containing 4-(1,3-diphenyl-1H-pyrazol-4-yl)-N-(morpholinomethyl)-6-arylpyrimidin-2-amines pooled with different bio-active heterocycles such as pyrazole, pyrimidine and morpholine derivatives. The structures of newly synthesized compounds were elucidated by IR, 1H NMR, 13C NMR and mass spectral data. The synthesized compounds were evaluated for their in vitro antimicrobial activity against different bacterial and fungal strains using Mueller-Hinton Broth dilution method. On the basis of SAR studies, it was observed that the presence of electron withdrawing groups remarkably enhanced the antimicrobial activity of synthesized compounds.

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A Novel and Efficient Synthesis of [1,2,3]-Triazolyl Substituted Benzo[c]Coumarins and Evaluation of their Antimicrobial Activity

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.70.1 ◽

2016 ◽

Vol 70 ◽

pp. 1-11

Author(s):

Neha N. Gohil ◽

Kaushik N. Kundaliya ◽

Dinkar I. Brahmbhatt

Keyword(s):

Antimicrobial Activity ◽

Fungal Pathogens ◽

Sodium Acetate ◽

Efficient Synthesis ◽

Mass Spectral Data ◽

Pyridinium Bromide ◽

Mass Spectral ◽

H Nmr ◽

Anti Fungal ◽

C Nmr

A series of novel [1,2,3]-triazolyl substituted benzo [c] coumarins have been synthesized by reacting various 3-coumarinoyl methyl pyridinium bromide salts with 1-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) ethanones in the presence of sodium acetate in refluxing acetic acid. The structures of the synthesized compounds have been elucidated by IR,1H-NMR,13C-NMR and Mass spectral data. All the synthesized compounds have been screened for theirinvitroanti-bacterial and anti-fungal activities. Some of the compounds have been found to be active against some bacterial and fungal pathogens compared to standard drugs.

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Isolation and Antimicrobial Activity of β-Sitosterol-3-O-Glucoside from Lannea Kerstingii Engl. & K. Krause (Anacardiacea)

Journal of Health and Allied Sciences NU ◽

10.1055/s-0040-1708607 ◽

2016 ◽

Vol 06 (01) ◽

pp. 004-008

Author(s):

Njinga N. S. ◽

Sule M. I. ◽

Pateh U. U. ◽

Hassan H. S. ◽

Abdullahi S. T. ◽

...

Keyword(s):

Antimicrobial Activity ◽

Wide Spectrum ◽

Diffusion Method ◽

Dilution Method ◽

Minimum Fungicidal Concentration ◽

E Coli ◽

H Nmr ◽

Vacuum Liquid Chromatography ◽

Broth Dilution ◽

C Nmr

AbstractThe emergence of more and more drug resistance bacteria has led to the study of the antimicrobial activity of the compound isolated from Lannea kerstingii Engl. & K. Krause (Anacardiacea) since the active principles of many drugs found in plants are secondary metabolites. A compound was isolated using dry vacuum liquid chromatography and eluting with CHCl3 -EtOAc and monitored using TLC. 3 1 13 The glycoside was characterized using 1 H NMR and 13 C NMR spectra recorded in DMSO-d6 at 400 MHz and 125 MHz, respectively. The antimicrobial activity of the compound was determined using agar diffusion method. The minimum inhibitory concentration (MIC) and minimum bactericidal/minimum fungicidal concentration (MBC/MFC) was determined using broth dilution method. The compound isolated was found to be β-sitosterol-3-O-glucoside. The β-sitosterol-3-O-glucoside (200μg/ml) was active against S. aureus, Methicillin Resistant Staphylococcus aureus, P. mirabilis, S. typhi, K. pneumoniae, E. coli, B. subtilis with zone of inhibition ranging from 24mm to 34mm and inactive against P. aeroginosa and Proteus vulgaris. It was also active against the fungi C. albicans and C. tropicalis but inactive against C. krusei. The MIC ranged from 25 to 50 μg/ml while the MBC/MFC ranged from 50 to 200 μg/ml. These results show the wide spectrum antimicrobial activity of β-sitosterol-3-O-glucoside.

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