Synthesis and antimicrobial activity of novel thienopyrimidine linked rhodanine derivatives

This work presents the preparation of a new series of N-(substituted phenyl)-2-(4-oxo-5-(4-(thieno[2,3-d]-pyrimidin-4-yloxy)benzylidene)-2-thioxothiazolidin-3-yl)acetamide derivatives (8a–8l). A condensation reaction of thienopyrimidin-2-thioxothiazolidin-4-one derivative (5) with various 2-chloro-N-phenylacetamides (7a–7l) was employed to afford the new thienopyrimidine tagged rhodanine derivatives under acetone solvent in the presence of potassium carbonate (K2CO3). All of the novel target molecules were characterized by IR, 1H NMR, 13C NMR, and LC–MS spectral analyses and were screened for their in vitro antimicrobial activity by using the broth dilution method. Compounds 8c, 8g, and 8h found to have antibacterial potency against E. coli, B. subtilis, B. cereus, and K. pneumonia with minimum inhibitory concentrations (MICs) of 3.25–6.25 μg/mL compared with the standard Gentamicin. Compounds 8c and 8f demonstrated better antifungal potency (MIC = 3.25–6.25 μg/mL) against A. flavus, A. niger, P. marneffei, and C. albicans when compared with Fluconazole.

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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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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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Synthesis, Spectral Analysis, In Vitro Microbiological Evaluation, and Molecular Docking Studies of Some Novel 1-(1-Aryl-1H-tetrazol-5-yl)-2-(piperidin-1-yl)ethanone Derivatives

ISRN Organic Chemistry ◽

10.1155/2014/120173 ◽

2014 ◽

Vol 2014 ◽

pp. 1-9 ◽

Cited By ~ 6

Author(s):

Thangasamy Elavarasan ◽

Durairaj Peter Bhakiaraj ◽

Mannathusamy Gopalakrishnan

Keyword(s):

Antimicrobial Activity ◽

Docking Studies ◽

Dilution Method ◽

Reference Drug ◽

Mass Spectral ◽

Drug Candidates ◽

H Nmr ◽

Serial Dilution Method ◽

C Nmr

A new series of novel heterocyclic compounds containing both tetrazoles and piperidine nuclei together, namely, 1-(1-aryl-1H-tetrazol-5-yl)-2-(piperidin-1-yl)ethanone (22–28), were synthesized by the treatment of the respective 2-chloro-1-(1-aryl-1H-tetrazol-5-yl)ethanone (15–21) with piperidine in acetonitrile for 6 h. A series of novel tetrazole substituted piperidine derivatives were synthesized and evaluated for their antimicrobial activity using serial dilution method. The structures of the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, mass spectral data, and elemental analysis. Evaluation of antimicrobial activity shows that several compounds exhibit good activity when compared with the reference drug candidates and thus could be promising new lead molecules.

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

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.57.13 ◽

2015 ◽

Vol 57 ◽

pp. 13-24 ◽

Cited By ~ 1

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.

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Synthesis and Antimicrobial Activity of Novel Series of Diversely Substituted Acetyl Pyrazoline Bearing Biphenyl Carbonitrile Motif

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.69.42 ◽

2016 ◽

Vol 69 ◽

pp. 42-48

Author(s):

Pineshkumar N. Patel ◽

Denish C. Karia

Keyword(s):

Antimicrobial Activity ◽

Mass Spectra ◽

Glacial Acetic Acid ◽

Mixed Solvent ◽

Dilution Method ◽

H Nmr ◽

Chemical Structures ◽

Ft Ir ◽

Broth Dilution ◽

C Nmr

Novel series of diversely substituted acetyl pyrazoline having biphenyl carbonitrile motif have been synthesized. The reaction of 2-cyno-4’-bromomethyl biphenyl with1-(4-hydroxy-phenyl)-ethanone resulted in acetophenone derivative of biphenyl-2-carbonitrile. This acetophenone derivative was condensed with substituted aromatic aldehyde in mixed solvent resulted in various substituted chalcones. These chalcones were further cyclized using hydrazine hydrate in presence of glacial acetic acid to produce titled compound derivatives. The chemical structures of synthesized compounds were elucidated by 1H-NMR, 13C-NMR FT-IR and mass spectra. Synthesized compounds were screened for their antimicrobial activity by broth dilution method. Out of twelve newly synthesized compounds, eight compounds are found to be equipotent to Ampicillin.

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Synthesis and antimicrobial activity of N-[4-(3-Oxo-3-phenyl-propenyl)-phenyl]-2-(4-phenyl-5-pyridine-4yl-4H-[1,2,4]triazole-3-ylsulfanyl)-acetamide

International Journal of Advances in Pharmaceutical Sciences ◽

10.5138/09761055.2034 ◽

2017 ◽

Vol 9 (2) ◽

pp. 43

Author(s):

Jyotindra Mahyavanshi ◽

Maharshi Shukla ◽

Kokila Parmar

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Nmr Spectroscopy ◽

The Novel ◽

H Nmr ◽

In Vitro Antibacterial Activity ◽

Ft Ir ◽

Anti Fungal ◽

New Compounds

A new series of N-[4-(3-Oxo-3-phenyl-propenyl)-phenyl]-2-(4-phenyl-5-pyridine-4yl-4H-[1,2,4]triazole-3-ylsulfanyl)-acetamide have been synthesized by the claisen-schimodt condensation of N-(4-Acetyl-phenyl)-2-(4-phenyl-5-pyridin-4-yl-4H-[1,2,4]triazole-3-ylsulfanyl) and various aldehyde. The novel compounds structure has been established on the basis of their substituted aldehyde derivatives. All the compounds were characterized by FT-IR, Mass, and 1H-NMR spectroscopy. These new compounds were evaluated for their in vitro antibacterial activity and anti-fungal activity.

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SYNTHESIS AND UTILITY OF NEW POLYCYCLIC COMPOUNDS AS POTENTIAL ANTIMICROBIALS BASED ON CHROMENE MOIETY

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2019v11i9.34338 ◽

2019 ◽

pp. 49-56

Author(s):

MAHMOUD N. ABDELAZIZ ◽

EMAN S. ZARIE ◽

ALAADIN E. SARHAN

Keyword(s):

Antimicrobial Activity ◽

Antibacterial Activity ◽

Condensation Reaction ◽

Ethyl Cyanoacetate ◽

Inhibition Zone ◽

Phenyl Isothiocyanate ◽

Polycyclic Compounds ◽

E Coli ◽

Multiple Species

Objective: The present research aims to synthesize some new polycyclic compounds including chromene moiety and study their antimicrobial activity. Methods: Several new polycyclic systems including chromene scaffold incorporated with pyridine, pyrimidine, imidazopyrimidine, and imidazodiazocine were achieved via condensation reaction of chromene derivative under the proper condition with various reagents namely; cyanothioacetamide, phenyl isothiocyanate, malononitrile, carbon disulfide, benzaldehyde, triethylorthoformate, and 1,4-dichlorobutane. Moreover, a chlorodiazenyl chromene derivative was reacted with some substances possessing active–CH2-bridge such as ethyl cyanoacetate and malononitrile to end up with hydrazono compounds. Such compounds were eventually cyclized with hydrazine hydrate to form pyrazole and oxopyrazole derivatives. Moreover, compound 1 was treated with benzoyl acetone, and then followed by cyclization with malononitrile to provide the corresponding 2-amino14-(4-methoxyphenyl)-4-methy-5-phenyl-14H-benzo[5,6] chromeno[2,3H][1,6]naphthyridine-3-carbonitrile (20). Results: The results of the antimicrobial screening in vitro revealed that the inhibition zone (mm) of the synthesized compounds 1-3, 5 and 8 implied their optimum antibacterial activity, while the compounds 4, 6 and 9-13, 15 showed a moderate to weak antibacterial activity against multiple species of B. subtilis, S. aureus, E. coli and P. aeruginosa. In contrast, the compounds 1, 6, 11, 15 showed high antifungal activities against different species of A. flavinand C. albicans, while the other compounds exhibit a moderate to poor antifungal activity. Conclusion: It is remarkable that a series of chromene derivatives synthesized by a simple and available method leads to a molecule of promising antimicrobial activity. Further research is recommended to approve the importance of polycyclic systems for various applications.

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

Organic Chemistry International ◽

10.1155/2014/419518 ◽

2014 ◽

Vol 2014 ◽

pp. 1-5 ◽

Cited By ~ 2

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.

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Synthesis and In Vitro Antimicrobial Activity of 3-(5-((2-Oxo-2H-Chromen-4-yl)Thio)-4-Phenyl-Thiazol-2-yl)-2-Substitutedphenyl Thiazolidin-4-One

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.51.135 ◽

2015 ◽

Vol 51 ◽

pp. 135-143

Author(s):

Himanshu R. Prajapati ◽

Harshad P. Lakum ◽

Kishor H. Chikhalia

Keyword(s):

Antimicrobial Activity ◽

Thioglycolic Acid ◽

Moderate Activity ◽

Mass Analysis ◽

Dilution Technique ◽

H Nmr ◽

Microbial Strain ◽

Broth Dilution ◽

C Nmr

An array of 3-(5-((2-oxo-2H-chromen-4-yl) thio)-4-phenyl thiazol-2-yl)-2-substitutedphenyl thiazolidin-4-one (7a-j) have been synthesized by using acetophenone, thiourea, 4-mercaptocoumarin and thioglycolic acid. The structures of these compounds were confirmed by IR, 1H NMR, 13C NMR and mass analysis. All the newly synthesized derivatives were evaluated for their in vitro antibacterial activity (against E.coli,P.aeruginosa,S.aureus, S. pyogenes) and antifungal activity against (C. albicans, A.niger, A.clavatus) using broth dilution technique. Some of the compounds showed good to moderate activity against the specific microbial strain.

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