Experimental and In-Silico Investigation of Anti-Microbial Activity of 1-Chloro-2-Isocyanatoethane Derivatives of Thiomorpholine, Piperazine and Morpholine (original) (raw)
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Synthesis and in vitro antibacterial activity of N -alkyl and N -aryl piperazine derivatives
2011
A series of N-alkyl and N-aryl substituted piperazine derivatives have been synthesized in order to evaluate their antibacterial activity against four Gram-positive (Streptococcus mutans MTCC 890, Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, Staphylococcus epidermidis MTCC 435) and one Gram-negative ( Escherichia coli MTCC 723) bacteria by disc diffusion and microbroth dilution methods. These compounds have been characterized by their MS, IR, 1 H and 13 C NMR spectral data. The benzyl piperazine derivatives 2-(4-benzylpiperazin-1-yl)-1-p-tolylethanone and 2-(4benzylpiperazin-1-yl)-1-(4-methoxyphenyl) ethanone show remarkable antibacterial activity even at low concentration against S. epidermidis , S. mutans and B. subtilis bacterial strains and are even close to the standard antibiotic, ampicillin. Furthermore, benzyl substitution increases antibacterial activity as compared to methyl and phenyl substituents under identical conditions.
Asian Journal of Chemistry, 2018
The compounds 1-(3-methoxy-1-phenyl-propyl)morpholine and 1-(3-methoxy-1-phenyl-propyl)piperidine have been synthesized using (3-methoxy-propenyl)benzene and 1-chloro-3-methoxy-propylbenzene. The structures of the synthesized compounds were analyzed by NMR and IR spectroscopic methods. Biological activities of obtained products were investigated against Gram-negative and Grampositive microorganisms. It has been showed that all the synthesized compounds possess pronounced antimicrobial activity against pathogenic bacteria Acinetobacter baumannii BDU32, Escherichia coli BDU12, Klebsiella pneumoniae BDU44, Pseudomonas aeruginosa BDU49 and Staphylococcus aureus BDU23.
Synthesis and biological activities of piperazine derivatives as antimicrobial and antifungal agents
Organic Communications, 2017
Apart from thiazole, benzimidazole, and tetrazole family, some of the piperazine analogs also show significant pharmacophoric activities. The synthesis of piperazine through intermediate 3 occurred via coupling of substituted benzenethiol with chloro-nitrobenzene. The nitro group of the isolated intermediate was reduced via an iron-acetic acid system. The aniline intermediate was cyclized with bis(2-chloroethyl)amine hydrochloride to obtain piperazine moiety. The synthesized substituted piperazine derivatives were screened for antibacterial and antifungal activities. The antibacterial activity was tested against Staphylococcus aureus, Streptomyces epidermidis, Pseudomonas aeruginosa and Escherichia coli, and antifungal activity was tested against Candida albicans, Aspergillus niger, Aspergillus flavus and Aspergillus fumigatus. As a result, many of the synthesized compounds showed significant antimicrobial and antifungal properties.
2012
Plan: To synthesize some novel 2-amino thiophenes with various substitutions at 2-amino position for antibacterial and antifungal activity. Prologue: Thiophenes containing organic compounds forms a significant group of drugs which exhibit an array of biological activities like anti-inflammatory, antibacterial, antifungal, anti-neoplastic, antiarthritic etc. Thus a series of new thiophenes have synthesized with various substituents at 2-amino position and screened for antimicrobial activity. Methodology: The parent compound 2-amino-3-(N-furfuryl amido)-4, 5-dimethyl thiophene was synthesized by condensing butan-2-one with furfurylcyano acetamide in presence of sulphur and diethylamine. It was then derivatized to various Schiff bases by reacting with various substituted aromatic aldehydes. The synthesized new compounds were characterized by MP, TLC, IR, NMR and Mass spectra and were screened for their antibacterial and antifungal activity by using Ampicillin and Miconazole nitrate as standard respectively. Outcome: The compounds MAI-2e, MAI-2k, & MAI-2l showed potent antibacterial and MAI-2a, MAI-2c, MAI-2e, & MAI-2f showed potent antifungal activity.
Antimicrobial Activity of Some Synthesized Piperazinyl Derivatives
2014
Some newly synthesized Schiff bases of N-methyl piperazine have been synthesized to study their antimicrobial potential. Thiazole substituted Schiff base namely 1’-[(N-methyl piperazino]-3’’nitro anilino]-2- benzilidine substituted 1,3-thiazole and oxazole substituted Schiff bases 1’-[(N-methyl piperazino]-3’’nitro anilino]-2- benzilidine substituted 1,3- oxazole were prepared by treating N-methyl piperazine with 3-chloro-2-nitro aniline leading to the formation of 3-nitro anilinoN-methyl piperazine. Chloroacetylation under anhydrous conditions gave the acetyl derivative which when further treated with thiourea and urea respectively led to the formation of piperazine substituted 2-amino thiazoles and 2amino oxazoles by indirect cyclization.Subsequent reaction with aromatic aldehydes gave the title comounds respectively. The compounds have responded to E.coli, S. aureus and C. albicans (in vitro) at 125 µg/disc and 250 µg/disc respectively.
Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives
Bioorganic & Medicinal Chemistry, 2006
A series of substituted piperazine derivatives have been synthesized and tested for antimicrobial activity. The antibacterial activity was tested against Staphylococcus aureus (MTCCB 737), Pseudomonas aeruginosa (MTCCB 741), Streptomyces epidermidis (MTCCB 1824) and Escherichia coli (MTCCB 1652), and antifungal activity against Aspergillus fumigatus, Aspergillus flavus and Aspergillus niger. All synthesized compounds showed significant activity against bacterial strains but were found to be less active against tested fungi. In vitro toxicity tests demonstrated that compounds 4d and 6a showed very less toxicity against human erythrocytes.N-Alkyl and N-aryl derivatives of piperazines have been synthesized and screened for antibacterial and antifungal activities. All the synthesized compounds show potent antibacterial activity and were found to be less active against fungi. Compounds 4d and 6a were found to be very less toxic to human erythrocytes when compared with gentamicin.
Synthesis and antimicrobial activity of morpholinyl/piperazinylbenzothiazines
Medicinal Chemistry Research
Structurally diverse morpholinyl/piperazinylbenzothiazines have been synthesized in quantitative yields by the reaction of substituted 1,4-benzothiazines with morpholine/N-(2-hydroxyethyl)piperazine. 1,4-Benzothiazines were prepared by the reaction of substituted 2-aminobenzenethiols with β-ketoesters. The structures of the synthesized compounds were confirmed by their analytical and spectroscopic data. The synthesized compounds were evaluated for their antimicrobial activity against bacterial species; E. coli and Bacillus cereus. Some of the synthesized compounds have shown significant activity against microorganisms.
Antimicrobial evaluation of trisubstituted 2-piperazinyl thiazoles
ACTA Pharmaceutica Sciencia, 2019
Bacterial resistance to the treatment of infectious diseases is the main problem. Many classes of antibiotics are facing resistance and have initiated new efforts to develop new derivatives and discover new chemical classes. 1 Gram positive and gram-negative bacteria such as Escherichia coli, Staphylococcus aureus, Micrococcus luteus, Bacillus subtilis, Bacillus cereus, Pseudomonas aeruginosa etc. are responsible for many diverse infections which even can cause of death. 2 Thiazole and basic nitrogen containing rings are important chemical moieties of antimicrobial drugs. Recently, third generation cefepime, ceftriaxone, cefix-ABSTRACT Thiazole and basic nitrogen containing rings are important chemical moieties of antimicrobial drugs. In recent, third generation cephalosporins include thiazole ring system. In this study, we synthesized 33 piperazine thiazole derivatives which were thought to show antimicrobial activity. Synthesize were realized with good yield using the method which reports the anticholinesterase properties of these compounds. Similar compounds with the same scaffold (2, 4, 5 trisubstituted thiazoles) are investigated for antimicrobial activity. Compounds 23-27 exhibited MIC: 256 µM against S. aureus ATCC 25923. Besides, 27-33 group showed MIC: 256 µM against K. pneumoniae UC57 and B. cereus. It is remarkable that the compound 27 showed antimicrobial activity against 4 different microorganisms and 26 showed antimicrobial activity against L. monocytogenes by MIC: 32 µM which is same as the standart chloramphenicol.
ChemInform, 2004
Pyrazolo[3,4-d]pyrimidines are one of the most important classes of fused heterocyclic compounds which exhibit a broad range of biological and medicinal properties. They are known as anticancer, antifungal, antibacterial, antiviral and anti-inflammatory agents. In this study, some new 6-substituted 4-amino-pyrazolo[3,4-d]pyrimidine derivatives were prepared via reaction of 5-amino-3methyl-1-phenyl-1H-pyrazole-4-carbonitrile with various nitriles in the presence of sodium ethoxide as catalyst. The inhibitory properties of synthesized compounds were studied according to CLSI guidelines against some pathogenic bacteria including four gram-positive strains (Streptococcus pyogenes, Staphylococcus aureus, Bacillus cereus and Bacillus subtilis subsp. spizizenii) and three gramnegative strains (Pseudomonas aeruginosa, Shigella flexneri and Salmonella enterica subsp. enterica). The antibacterial effects of all derivatives were compared with those of antibiotics belonging to different classes. The values were reported as inhibition zone diameter (IZD), minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC). The effect of substituents on the biological activity of derivatives was discussed as well. The inhibitory effect of compound 6a, was shown to be the most, with MIC values in the range of 32-4096 lg/mL. Since most of the synthesized compounds were effective against Streptococcus pyogenes and Pseudomonas aeruginosa, they can be considered as inhibitors of these two bacteria.
European Journal of Medicinal Chemistry, 2007
Cyano derivatives of N-alkyl and N-aryl piperazine have been synthesized and screened for antibacterial and antifungal activities. All the synthesized compounds showed the antibacterial activity against pathogenic strains of Staphylococcus aureus (MTCCB 737), Pseudomonas aeruginosa (MTCCB 741), Streptomyces epidermidis (MTCCB 1824) and Escherichia coli (MTCCB 1652) and antifungal activity against pathogenic strains of Aspergillus fumigatus (ITCC 4517), Aspergillus flavus (ITCC 5192) and Aspergillus niger (ITCC 5405). All compounds showed mild to moderate antimicrobial activity. However, compounds 3c, 4a and 6 showed potent antibacterial activity against pathogenic strains used in the study. Compounds 3a, 3b, 4b, and 4d showed mild to moderate antifungal activity against Aspergillus pathogenic strains. The compounds reported in this study were assessed for there cytotoxicity using MTT colorimetric assay on Hela cells. All the compounds showed cell viability more than the control drug gentamicin, with compound 2 having highest i.e. 95% cell viability.A series of cyano derivatives of N-alkyl and N-aryl piperazine were synthesized and evaluated for antibacterial and antifungal activity. Compound 3-(4-methyl-piperazin-1-yl)-propanitrile 4a showed potent antibacterial activity by broth dilution method with MIC at 19.5 μg/ml and 39.0 μg/ml against P. aeruginosa and E. coli, respectively, comparable to gentamicin as control drug. Compounds (4-benzyl-piperazin-1-yl)-acetonitrile 3c and 3-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-acetonitrile 6 showed a significant antibacterial activity with MIC at 19.5 μg/ml against S. aureus. In vitro cytotoxic studies of compound 3b exhibit 95% cell viability at the concentration used for antibacterial studies on Hela cells by using MTT colorimetric method.