Synthesis and Antimicrobial Study of New Benzimidazole Schiff Bases Bearing P-Toluene Sulfonamide Moiety (original) (raw)
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Benzimidazole Schiff base derivatives: synthesis, characterization and antimicrobial activity
BMC Chemistry
A series of Schiff bases (3.a–f) bearing benzimidazole moiety was successfully synthesized in ethanol by refluxing Oct-2-ynoic acid (1,3-dihydrobenzimidazole-2-ylidene)amide with substituted amines. Fourier transform infrared (FTIR), ultra violet light (UV–VIS), elemental analysis, proton (1H) and carbon (13C) nuclear magnetic resonance spectroscopy were used to characterize the newly synthesized Schiff bases. Micro dilution method was used to determine the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of the Schiff bases, against 14 human pathogenic bacteria (8 Gram negative and 6 Gram positive) and against 7 fungal strains (5 Aspergillus and 2 Fusarium) representatives. Antimalarial activity against Plasmodium falciparum and antitrypanosomal property against Trypanosoma brucei was studied in vitro at a single dose concentration of the Schiff bases. Cytotoxicity of the Schiff bases was assessed against human cervix adenocarcinoma (HeLa) cells. Re...
Synthesis of Benzimidazole Derivatives Containing Schiff Base Exhibiting Antimicrobial Activities
International Journal of Research Studies in Biosciences, 2017
A series of 2-substituted Benzimidazole having imine linkage were synthesized by two step reactions. In the first step, o-phenylenediamine was condensed with p-amino benzoic acid in xylene and poly phosphoric acid to give 2-amino Benzimidazole. In the second step, 2-amino Benzimidazole is treated with different substituted aldehydes and ketones to form substituted Benzimidazole having imine linkage. The synthesized compounds were evaluated for anti-bacterial activity against Staphylococcus aureus and Escherichia coli by tube dilution method. The compounds SAM-2 and SAM-10 were found to be more potent than standard drug vancomycin against Gram (+) ve and Gram (-) ve bacteria. The compounds SAM-4 and SAM-9 had antimicrobial activity comparable to standard drugs against both the microorganisms. The aims of this study to synthesize novel benzimidazole derivatives containing Schiff's base and evaluate the antimicrobial activity of the synthesized derivatives against S. aureus and E. coli.
International Journal of Research Studies in Biosciences, 2017
A series of 2-substituted Benzimidazole having imine linkage were synthesized by two-step reactions. In the first step, o-phenylenediamine was condensed with p-amino benzoic acid in xylene and polyphosphoric acid to give 2-amino Benzimidazole. In the second step, 2-amino Benzimidazole is treated with different substituted aldehydes and ketones to form Substituted Benzimidazole having imine linkage. The synthesized compounds were evaluated for antibacterial activity against Staphylococcus aureus and Escherichia coli by tube dilution method. The compounds SAM-2 and SAM-10 were found to be more potent than standard drug vancomycin against Gram (+) ve and Gram (–) ve bacteria. The compounds SAM-4 and SAM-9 had antimicrobial activity comparable to standard drugs against both the microorganisms. The aims of this study to synthesize novel benzimidazole derivatives containing Schiff’s base and evaluate the antimicrobial activity of the synthesized derivatives against S. aureus and E. coli.
Antibacterial Screening of New Synthesis Schiff Base having Benzimidazole Moiety
Asian Journal of Chemistry, 2018
The derivatives of benzimidazole are a crucial class of the bioactive molecules in the field of pharmaceuticals and drugs [1]. The derivatives benzimidazole have occupied a prominent position in medicinal chemistry because of their significant properties as a treatment in clinical applications. Benzimidazole is a versatile pharmacophore producing a different range of biological activities [2], including analgesic [3] and antiinflammatory [4-6]. Benzimidazole derivatives have found the application in different therapeutic areas including, antihypertensive [7], antiviral [8,9], antifungal [10-12], anticancer [13-15], antitubercular [16,17], antioxidant [18,19], antimicrobial [20-23], antibacterial [24-26]. Benzimidazole derivatives are highly active against several viruses such as HIV, herpes (HSV-1), RNA, influenza and human cytomegalovirus (HCMV) [27]. Some benzimidazole derivatives have been noted as thyroid receptor stimulants. Also widely used as drugs such as proton pump inhibitor omeprazole [25]. Schiff bases considered as important class of organic compounds, especially in the medicinal and pharmaceutical field. Thus, synthesis and development of novel Schiff base derivatives as potential chemotherapeutics still attract attention of organic and medicinal chemist [28]. Schiff bases derived mostly from different set of heterocyclic rings, were reported to possess a broad spectrum and wide range of biological activities including antibacterial [29] and antimicrobial [30].
Journal of Molecular Structure, 2021
A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3a-c were condensed with cyanothioacetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4a-c, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5a-c. The esters 5a-c were cyclized by action of sodium methoxide to aminoesters 6a-c, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6a-c were hydrolyzed with NaOH to the corresponding sodium salt 8a-c, which were treated with acetic anhydride to afford 2-methyloxazinones 9a-c. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10a-c, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11a-c. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs.
Rasayan Jouranal of Chemistry http://www.rasayanjournal.com Vol.3, No.1 (2010),51-54, 2010
The novel reaction of 3-(2-methylbenzimidazol-1-yl) propanoic acid hydrazide with CS2/KOH gave Oxadiazole derivative which under went Mannich reaction to give 3-[(dialkylamino) methyl]-2phenyl-4(3H)-quinazolinone. All compounds were characterized by physical, chemical, analytical and spectral data. All compounds have been screened for their antimicrobial activity and anti-inflammatory activity. Keywords: 4(3H)-Quinazolinones,Niementowski Reaction, N-Mannich reaction, Antimicrobial agent.
Zanco Journal of Medical Sciences
aimed to synthesize several 4-hydroxyl benzaldehyde derivatives by a substitution reaction with different alkyl halide followed Background and objective: Compounds having imine or azomethine (-C=N-) functional group are known as Schiff bases. Schiff bases compounds are found to be an active pharmacophore for the design and development of various bioactive lead compounds. In this study, several new Schiff base compounds have been synthesized and characterized. Methods: Williamson ether synthesis process has been used to synthesize-alkyloxy and substituted benzyloxy of benzaldehyde. Differently substituted ether benzaldehydes used to react with 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one in one hand and 1H-benzo[d]imidazol-2-amine on the other hand to produce Schiff base compounds. Results: Synthesized ether derivative compounds (3a-e) were converted to new series of Schiff bases (4a-e and 5a-e) by condensation of equal molar amounts of compounds (3a-e) with different heterocyclic amines dissolved in absolute ethanol. All synthesized compounds were confirmed by (IR, 1 H-NMR, and 13 CNMR) spectroscopy. All synthesized compounds were evaluated for antibacterial activities in vitro against Gram-positive and Gram-negative bacteria. Conclusion: All compounds were purely synthesized, and all compounds were indicated growth inhibition against Escherichia coli, and Staphylococcus aureus, respectively with different inhibition zones staring from 13 to 33 mm.
Synthesis and Antimicrobial Study of Some Schiff Bases of Sulfonamides
Objective: The purpose of research was to synthesize the better antimicrobial compounds usingDifferent substituted aromatic aldehydes are chosen as the starting material for the synthesis ofSchiff’s Bases with sulfonamide helps to formation of Schiff bases in presences of alcohol and acidicreagent.Material and methods: Melting points of the synthesized compounds were determined by opencapillary and are uncorrected. The purity of the compounds was checked using precoated TLC plates(MERCK, 60F) using chloroform: methanol (8:2) solvent system. The developed chromatographicplates were visualized under UV at 254nm. IR spectra were recorded using KBr on Shimadzu FTIRmodel 8400 spectrophotometer, 1H NMR spectra in DMSO on a BRUKER FT-NMR instrument usingTMS as internal standard.Results : All the synthesized compounds (Ia-Ij) were purified by successive recrystallization usingethanol. The purity of the synthesized compounds was checked by performing TLC. The structures ofthe synthesized com...
2020
Novel benzothiazole Schiff bases namely N-(4-chlorobenzylidene)-4,6-difluorobenzothiazole-2-amine; 4,6-difluoro-N-(4nitrobenzylidene)benzothiazol-2-amine and N-((1H-indol-3-yl)methylene)-4,6-difluorobenzothiazole-2-amine have been synthesized from condensation reaction of 4,6-difluoro-2-amino benzothiazole with different aromatic aldehydes like 4-chlorobenzaldehyde, 4-nitrobenzaldehyde and 1H-indole-3-cardaldehyde. The structures of all the compounds were characterized by elemental analysis, FT-IR, Mass and 1H-NMR spectroscopy. Schiff bases have been screened for antimicrobial activity against bacteria and fungi by using MIC determination. In vitro antibacterial and antifungal activity of ligands were assayed against gram positive (S. Aureus, B.Subtilis), gram negative bacteria (S. Marcescens, E. coli) and Rhizopus sp. and A. Niger. The standard drugs ketoconazole and ciprofloxacin were used to screen antimicrobial activity.
Synthesis and Antibacterial Evaluation of Some Novel Imidazole and Benzimidazole Sulfonamides
Several new substituted sulfonamide compounds were synthesized and their structures were confirmed by 1 H-NMR, 13 C-NMR, FT-IR, and mass spectroscopy. The antibacterial activities of the synthesized compounds were screened against standard strains of six Gram positive and four Gram negative bacteria using the microbroth dilution assay. Most of the compounds studied showed promising activities against both types of bacteria.