Synthesis and Antimicrobial Activity of Some New N-(1H-benzimidazol-2- yl)-2-mercaptoacetamide Derivatives

2018 ◽  
Vol 15 (2) ◽  
pp. 154-159
Author(s):  
Asaf Evrim Evren ◽  
Sinem Tekinkoca ◽  
Leyla Yurttas
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Bacterial Resistance ◽  
Fungal Infections ◽  
Antimicrobial Activities ◽  
Benzimidazole Derivatives ◽  
Standard Drug ◽  
E Coli ◽  
Pharmacological Significance ◽  
Anti Fungal

Background: Due to multi-drug, extended-drug, and pandrug resistance phenotypes, bacterial resistance to antibiotics and fungal infections are a general health issue. Particulary, increase of fungal infections due to secondary cause of human diseases have been observed. An extensive variety of benzimidazole derivatives have been characterized for their chemotherapeutic significance. Benzimidazole derivatives have received important attention because of pharmacological significance during current years, especially antimicrobial, anti-fungal, antitubercular, antioxidant, anti-Alzheimer's disease and antihypertension activities. Methods: Some N-(1H-benzimidazol-2-yl)-2-mercaptoacetamide derivatives (2a-h) were synthesised and evaluated for their antimicrobial activity. The title compounds were gained by reacting N-(1H-benzimidazol-2-yl)-2-chloroacetamide with some substituted 2-mercapto heterocyclic rings. The synthesised compounds were investigated for their antimicrobial activities against C. albicans (ATCC 24433), C. krusei (ATCC 6258), C. glabrata (ATCC90030), C. parapsilosis (ATCC 22019), E. coli (ATCC 25922), E. coli (ATCC 35218), E. feacalis (ATCC 51299), E. feacalis (ATCC 29212), S. aureus (ATCC 25923), K. pneumoniae (ATCC 700603), P. aeruginosa (ATCC 27853). Results: The compounds showed high antifungal activity when compared with standard drug ketoconazole. In addition, all compounds (MIC 100 µg/mL) showed inhibitor activity against P. aeruginosa at two fold concentration of chloramphenicol (MIC 50 µg/mL). Also, compounds 2a, 2c and 2e (MIC: 50 µg/mL) have equal effect against E. coli (ATCC 35218) and more effective than other compounds (MIC of chloramphenicol: 100 µg/mL). Conclusıon: All compounds showed notable activity. Compounds have determined to possess higher antifungal activity than antibacterial activity. Additionally, compounds 2a with 1-methyltetrazole, 2c with benzothiazole and 2e with 6-chlorobenzothiazole moieties were found as the most active compounds.

Preliminary phytochemical screening and antimicrobial activities of plant extract of Elaeocarpus ganitrus Roxb.

2016 ◽  
Vol 5 (09) ◽  
pp. 4885 ◽  
Author(s):  
Khushbu Pandey ◽  
Mahendra Singh* ◽  
Bharat Pandey ◽  
Anshulika Upadhyaya ◽  
Kamal K. Pande
Keyword(s):  
Antimicrobial Activity ◽  
Rhizopus Oryzae ◽  
Antimicrobial Activities ◽  
Diffusion Method ◽  
Phytochemical Analysis ◽  
Phytochemical Screening ◽  
Bacterial Strains ◽  
E Coli ◽  
Antibacterial And Antifungal ◽  
Anti Fungal

The present study was carried out for phytochemical screening of principle bioactive compounds and antimicrobial activity in Elaeocarpus ganitrus Roxb., Phytochemical analysis revealed the presence of saponin, terpenoid, steroid, saponin, flavonoid, tannin and alkaloid. The petroleum, ether, chloroform, methanol, acetone and aqueous extracts were subjected to antimicrobial activity against bacterial strains Staphylococcus aureus, Pseudomonas, E. coli and Bacillus subtilis against anti-fungal strains A.awamori, A.fumigatus, Rhizopus oryzae, Trichoderma viridae and C.oryzae. The antibacterial and antifungal activity was evaluated by disc-diffusion method.

scholarly journals EVALUATION OF ANTIFUNGAL AND ANTIBACTERIAL ACTIVITY OF SOME NEW BENZIMIDAZOLE DERIVATIVES

2018 ◽  
Vol 48 (2) ◽  
pp. 125-129
Author(s):  
K. ZOMORODIAN ◽  
S. KHABNADIDEH ◽  
L. ZAMANI ◽  
K. PAKSHIR ◽  
M. TAJADDOD
Keyword(s):  
Antifungal Activity ◽  
Fungal Infections ◽  
Antimicrobial Activities ◽  
Antifungal Drugs ◽  
In Vivo Studies ◽  
Benzimidazole Derivatives ◽  
Dilution Method ◽  
Gram Positive ◽  
Meta Position

The extensive use of antifungal drugs and their resistance against fungal infections have led to discover new antimicrobial compounds. We previously described synthesis of some new derivatives of 2-methylbenzimidazole (1a-5a) and 5,6dimethylbenzimidazol (1b-5b). Here we evaluated the antimicrobial activities of these compounds against different species of micro organisms including gram positive and gram negative bacteria as well as fungi. Broth micro-dilution method as recommended by clinical and laboratory standard institute (CLSI) was used for this purpose. The results show compounds 2-Methyl-1-(3-methylbenzyl)-1H-benzo [d]imidazole (5a) and 5,6-Dimethyl-1-(3-methyl benzyl)-1H-benzo[d]imidazole (5b) had the best antifungal activity against the examined fungi and gram positive bacteria. Moreover these two compounds inhibited the growth of azole resistant strains. By comparison the relationship between the structures and activities of the tested compounds revealed that the presence of methyl residue in meta position of benzyl group enhance the antifungal activity. Regarding a broad spectrum antifungal activities of some of the tested compounds, they might be a good candidate for further in vivo studies to evaluate their pharmacological activity and toxicity as a novel antifungal agents.

scholarly journals Facile Synthesis, Characterization, and In Vitro Antimicrobial Screening of a New Series of 2,4,6-Trisubstituted-s-triazine Based Compounds

2015 ◽  
Vol 2015 ◽  
pp. 1-10
Author(s):  
Ravi Bhushan Singh ◽  
Nirupam Das ◽  
Md. Kamaruz Zaman
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Elemental Analysis ◽  
Broad Spectrum ◽  
Antibacterial Efficacy ◽  
Facile Synthesis ◽  
Standard Drug ◽  
E Coli

A series of new 2,4,6-trisubstituted-s-triazine was synthesized, assessed for antimicrobial activity, and characterized by FTIR, 1HNMR, 13CNMR, and elemental analysis. The tested compounds, 4d, 4g, 4h, 4k, and 4n, have shown considerable in vitro antibacterial efficacy with reference to the standard drug ciprofloxacin (MIC 3.125 μgmL−1 against B. subtilis, E. coli, and K. pneumoniae). It was observed that compounds 4d and 4h displayed equipotent antibacterial efficacy against B. subtilis (MIC 3.125 μgmL−1) and S. aureus (MIC 6.25 μgmL−1). The studies demonstrated that the para-fluorophenylpiperazine substituted s-triazine (4n) was potent and exhibited broad spectrum antibacterial activity against S. epidermidis, K. pneumoniae, and P. aeruginosa with MIC of 6.25 μgmL−1 and for E. coli, it showed an MIC of 3.125 μgmL−1 equipotent with reference to the standard drug. Among all the compounds under investigation, compound 4g also demonstrated significant antifungal activity (3.125 μgmL−1) against C. albicans.

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

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.

Substituted 6,7-dimethoxy-5-oxo-2,3,5,9b-tetrahydrothiazolo[2,3-a]isoindole- 3-1,1-dioxide Derivatives with Antimicrobial Activity and Docking Assisted Prediction of the Mechanism of their Antibacterial and Antifungal Properties

2020 ◽  
Vol 20 (29) ◽  
pp. 2681-2691
Author(s):  
Athina Geronikaki ◽  
Victor Kartsev ◽  
Phaedra Eleftheriou ◽  
Anthi Petrou ◽  
Jasmina Glamočlija ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Drug Targets ◽  
Bacterial Species ◽  
Pharmaceutical Research ◽  
Docking Studies ◽  
Fungal Species ◽  
Docking Analysis ◽  
E Coli ◽  
Antibacterial And Antifungal

Background: Although a great number of the targets of antimicrobial therapy have been achieved, it remains among the first fields of pharmaceutical research, mainly because of the development of resistant strains. Docking analysis may be an important tool in the research for the development of more effective agents against specific drug targets or multi-target agents 1-3. Methods: In the present study, based on docking analysis, ten tetrahydrothiazolo[2,3-a]isoindole derivatives were chosen for the evaluation of the antimicrobial activity. Results: All compounds showed antibacterial activity against eight Gram-positive and Gram-negative bacterial species being, in some cases, more potent than ampicillin and streptomycin against all species. The most sensitive bacteria appeared to be S. aureus and En. Cloacae, while M. flavus, E. coli and P. aeruginosa were the most resistant ones. The compounds were also tested for their antifungal activity against eight fungal species. All compounds exhibited good antifungal activity better than reference drugs bifonazole (1.4 – 41 folds) and ketoconazole (1.1 – 406 folds) against all fungal species. In order to elucidate the mechanism of action, docking studies on different antimicrobial targets were performed. Conclusion: According to docking analysis, the antifungal activity can be explained by the inhibition of the CYP51 enzyme for most compounds with a better correlation of the results obtained for the P.v.c. strain (linear regression between estimated binding Energy and log(1/MIC) with R 2 =0.867 and p=0.000091 or R 2 = 0.924, p= 0.000036, when compound 3 is excluded.

scholarly journals Synergistic Antimicrobial Activities of Combinations of Vanillin and Essential Oils of Cinnamon Bark, Cinnamon Leaves and Cloves

Foods ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1406
Author(s):  
Rita Cava-Roda ◽  
Amaury Taboada-Rodríguez ◽  
Antonio López-Gómez ◽  
Ginés Benito Martínez-Hernández ◽  
Fulgencio Marín-Iniesta
Keyword(s):  
Antimicrobial Activity ◽  
Essential Oils ◽  
Food Packaging ◽  
Antimicrobial Effect ◽  
Antimicrobial Activities ◽  
Inhibitory Effects ◽  
Cinnamon Bark ◽  
E Coli ◽  
Pure Compounds ◽  
Main Component

Plant bioactive compounds have antimicrobial and antioxidant activities that allow them to be used as a substitute for synthetic chemical additives in both food and food packaging. To improve its sensory and bactericidal effects, its use in the form of effective combinations has emerged as an interesting possibility in the food industry. In this study, the antimicrobial activities of essential oils (EOs) of cinnamon bark, cinnamon leaves, and clove and the pure compounds vanillin, eugenol, and cinnamaldehyde were investigated individually and in combination against Listeria monocytogenes and Escherichia coli O157:H7. The possible interactions of combinations of pure compounds and EOs were performed by the two-dimensional checkerboard assay and isobologram methods. Vanillin exhibited the lowest antimicrobial activity (MIC of 3002 ppm against L. monocytogenes and 2795 ppm against E. coli O157:H7), while clove and cinnamon bark EOs exhibited the highest antimicrobial activity (402–404 against L. monocytogenes and 778–721 against E. coli O157:H7). For L. monocytogenes, pure compound eugenol, the main component of cinnamon leaves and clove, showed lower antimicrobial activity than EOs, which was attributed to the influence of the minor components of the EOs. The same was observed with cinnamaldehyde, the main component of cinnamon bark EO. The combinations of vanillin/clove EO and vanillin/cinnamon bark EO showed the most synergistic antimicrobial effect. The combination of the EOs of cinnamon bark/clove and cinnamon bark/cinnamon leaves showed additive effect against L. monocytogenes but indifferent effect against E. coli O157:H7. For L. monocytogenes, the best inhibitory effects were achieved by cinnamon bark EO (85 ppm)/vanillin (910 ppm) and clove EO (121 ppm)/vanillin (691 ppm) combinations. For E. coli, the inhibitory effects of clove EO (104 ppm)/vanillin (1006 ppm) and cinnamon leaves EO (118 ppm)/vanillin (979 ppm) combinations were noteworthy. Some of the tested combinations increased the antimicrobial effect and would allow the effective doses to be reduced, thereby offering possible new applications for food and active food packaging.

scholarly journals An Antifungal Benzimidazole Derivative Inhibits Ergosterol Biosynthesis and Reveals Novel Sterols

2015 ◽  
Vol 59 (10) ◽  
pp. 6296-6307 ◽  
Author(s):  
Petra Keller ◽  
Christoph Müller ◽  
Isabel Engelhardt ◽  
Ekkehard Hiller ◽  
Karin Lemuth ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Fungal Infections ◽  
Transcriptional Profiling ◽  
Benzimidazole Derivative ◽  
Benzimidazole Derivatives ◽  
Ergosterol Biosynthesis ◽  
Screening Assay ◽  
Content Type ◽  
Life Threatening ◽  
A Cell

ABSTRACTFungal infections are a leading cause of morbidity and death for hospitalized patients, mainly because they remain difficult to diagnose and to treat. Diseases range from widespread superficial infections such as vulvovaginal infections to life-threatening systemic candidiasis. For systemic mycoses, only a restricted arsenal of antifungal agents is available. Commonly used classes of antifungal compounds include azoles, polyenes, and echinocandins. Due to emerging resistance to standard therapies, significant side effects, and high costs for several antifungals, there is a need for new antifungals in the clinic. In order to expand the arsenal of compounds with antifungal activity, we previously screened a compound library using a cell-based screening assay. A set of novel benzimidazole derivatives, including (S)-2-(1-aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole (EMC120B12), showed high antifungal activity against several species of pathogenic yeasts, includingCandida glabrataandCandida krusei(species that are highly resistant to antifungals). In this study, comparative analysis of EMC120B12 versus fluconazole and nocodazole, using transcriptional profiling and sterol analysis, strongly suggested that EMC120B12 targets Erg11p in the ergosterol biosynthesis pathway and not microtubules, like other benzimidazoles. In addition to the marker sterol 14-methylergosta-8,24(28)-dien-3β,6α-diol, indicating Erg11p inhibition, related sterols that were hitherto unknown accumulated in the cells during EMC120B12 treatment. The novel sterols have a 3β,6α-diol structure. In addition to the identification of novel sterols, this is the first time that a benzimidazole structure has been shown to result in a block of the ergosterol pathway.

In silico designing of some Benzimidazole derivatives for Anti-fungal activity

2021 ◽  
pp. 4983-4986
Author(s):  
Amrita Muralikrishnan ◽  
Radhika R Nair ◽  
Jifitha Banu ◽  
Leena K Pappachen
Keyword(s):  
Fungal Infections ◽  
Living Organism ◽  
Whole Body ◽  
Benzimidazole Derivatives ◽  
Bioinformatics Tool ◽  
Pharmacological Activities ◽  
Discovery Studio ◽  
Drug Designing ◽  
Target Molecules ◽  
Anti Fungal

Fungus is a kind of living organism and yeast mould and mushrooms are types of fungi. The fungal infections are caused by the fungus. A fungus that invades the tissue can cause a disease that confined to the skin, spread into tissue, bone and organs or affect the whole body. Benzimidazole is a class of heterocyclic aromatic organic compound which posses pharmacological activities including antifungal, antitumor, antiparasitic, analgesic etc. Insilico methods can be used to identify target molecules using bioinformatics tool. The aim of our study was to conduct the insilico drug designing of some benzimidazole derivatives having antifungal activities. In our study the insilico drug design was performed using Biovia discovery studio.

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 3-Amino-5-(indol-3-yl)methylene-4-oxo-2-thioxothiazolidine Derivatives as Antimicrobial Agents: Synthesis, Computational and Biological Evaluation

2020 ◽  
Vol 13 (9) ◽  
pp. 229
Author(s):  
Volodymyr Horishny ◽  
Victor Kartsev ◽  
Vasyl Matiychuk ◽  
Athina Geronikaki ◽  
Petrou Anthi ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Biological Evaluation ◽  
Minimal Bactericidal Concentration ◽  
Active Compounds ◽  
Hek 293 ◽  
E Coli ◽  
Thiazolyl Blue Tetrazolium Bromide

Herein we report the design, synthesis, computational, and experimental evaluation of the antimicrobial activity of fourteen new 3-amino-5-(indol-3-yl) methylene-4-oxo-2-thioxothiazolidine derivatives. The structures were designed, and their antimicrobial activity and toxicity were predicted in silico. All synthesized compounds exhibited antibacterial activity against eight Gram-positive and Gram-negative bacteria. Their activity exceeded those of ampicillin and (for the majority of compounds) streptomycin. The most sensitive bacterium was S. aureus (American Type Culture Collection ATCC 6538), while L. monocytogenes (NCTC 7973) was the most resistant. The best antibacterial activity was observed for compound 5d (Z)-N-(5-((1H-indol-3-yl)methylene)-4-oxo-2-thioxothiazolidin-3-yl)-4-hydroxybenzamide (Minimal inhibitory concentration, MIC at 37.9–113.8 μM, and Minimal bactericidal concentration MBC at 57.8–118.3 μM). Three most active compounds 5d, 5g, and 5k being evaluated against three resistant strains, Methicillin resistant Staphilococcus aureus (MRSA), P. aeruginosa, and E. coli, were more potent against MRSA than ampicillin (MIC at 248–372 μM, MBC at 372–1240 μM). At the same time, streptomycin (MIC at 43–172 μM, MBC at 86–344 μM) did not show bactericidal activity at all. The compound 5d was also more active than ampicillin towards resistant P. aeruginosa strain. Antifungal activity of all compounds exceeded those of the reference antifungal agents bifonazole (MIC at 480–640 μM, and MFC at 640–800 μM) and ketoconazole (MIC 285–475 μM and MFC 380–950 μM). The best activity was exhibited by compound 5g. The most sensitive fungal was T. viride (IAM 5061), while A. fumigatus (human isolate) was the most resistant. Low cytotoxicity against HEK-293 human embryonic kidney cell line and reasonable selectivity indices were shown for the most active compounds 5d, 5g, 5k, 7c using thiazolyl blue tetrazolium bromide MTT assay. The docking studies indicated a probable involvement of E. coli Mur B inhibition in the antibacterial action, while CYP51 inhibition is likely responsible for the antifungal activity of the tested compounds.

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