Synthesis and Biological Evaluation of Benzothiazole-piperazinesulfonamide Conjugates and Their Antibacterial and Antiacetylcholinesterase Activity

Two series of N-2-benzothiazolyl-4-(arylsulfonyl)-1-piperazineacetamides/propanamides were synthesized from substituted 2-aminobenzothiazoles and were assayed for their in vitro antimicrobial activities against a panel of different pathogenic bacterial strains such as Micrococcus luteus, S. aureus, S. aureus MLS-16, B. subtilis, Escherichia coli, Pseudomonas aeruginosa, Klebsiella planticola and Candida albicans. Among the synthesized compounds 5e,f,g and 6g,h,i showed promising antifungal activity against C. albicans as compared to the reference drug, miconazole. Further, compounds 6g,h,i showed broad spectrum antibacterial activity against all the tested bacterial strains, while the compounds 6a-f,j-m showed significant antibacterial activity against all the tested bacterial strains as compared to the reference drug, ciprofloxacin. In addition, the target compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity, and, among the tested, compounds 5j,k,l and 6i showed promising AChE inhibitory activity.

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N-(Hydroxyalkyl) Derivatives of tris(1H-indol-3-yl)methylium Salts as Promising Antibacterial Agents: Synthesis and Biological Evaluation

Pharmaceuticals ◽

10.3390/ph13120469 ◽

2020 ◽

Vol 13 (12) ◽

pp. 469

Author(s):

Sergey N. Lavrenov ◽

Elena B. Isakova ◽

Alexey A. Panov ◽

Alexander Y. Simonov ◽

Viktor V. Tatarskiy ◽

...

Keyword(s):

Antibacterial Activity ◽

Antimicrobial Agents ◽

Carbon Chain ◽

Biological Evaluation ◽

Carbon Chain Length ◽

Klebsiella Pneumonia ◽

Moderate Activity ◽

Bacterial Strains ◽

Reference Drug

The wide spread of pathogens resistance requires the development of new antimicrobial agents capable of overcoming drug resistance. The main objective of the study is to elucidate the effect of substitutions in tris(1H-indol-3-yl)methylium derivatives on their antibacterial activity and toxicity to human cells. A series of new compounds were synthesized and tested. Their antibacterial activity in vitro was performed on 12 bacterial strains, including drug resistant strains, that were clinical isolates or collection strains. The cytotoxic effect of the compounds was determined using an test with HPF-hTERT (human postnatal fibroblasts, immortalized with hTERT) cells. The activity of the obtained compounds depended on the carbon chain length. Derivatives with C5–C6 chains were more active. The minimum inhibitory concentration (MIC) of the most active compound on Gram-positive bacteria, including MRSA, was 0.5 μg/mL. Compounds with C5–C6 chains also revealed high activity against Staphylococcus epidermidis (1.0 and 0.5 μg/mL, respectively) and moderate activity against Gram-negative bacteria Escherichia coli (8 μg/mL) and Klebsiella pneumonia (2 and 8 μg/mL, respectively). However, they have no activity against Salmonella cholerasuis and Pseudomonas aeruginosa. The most active compounds revealed higher antibacterial activity on MRSA than the reference drug levofloxacin, and their ratio between antibacterial and cytotoxic activity exceeded 10 times. The data obtained provide a basis for further study of this promising group of substances.

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Synthesis and Biological Evaluation of Acetylcholinesterase Inhibitor Macakurzin C and Its Derivatives

Synlett ◽

10.1055/s-0034-1380193 ◽

2015 ◽

Vol 26 (08) ◽

pp. 1131-1134 ◽

Cited By ~ 3

Author(s):

Hyoungsu Kim ◽

Seung-Hoon Baek ◽

Hongjun Jang

Keyword(s):

Inhibitory Activity ◽

Acetylcholinesterase Inhibitor ◽

Biological Evaluation ◽

Hydroxyl Groups ◽

Structural Requirements ◽

Ache Inhibitory Activity ◽

Synthesis And Biological Evaluation ◽

Derivatives Of

The derivatives of macakurzin C containing a modified D ring and protected C(3)/C(5)-hydroxyl groups were synthesized and their in vitro AChE inhibitory activity and neurotoxicity were evaluated to identify the structural requirements for the activities. The results indicated that C(3)-benzyl-protected derivative has a more potent AChE inhibitory activity (IC50, 2.6 μM) and a less neurotoxicity (GI50, >100 μM) than synthetic macakurzin C (IC50, 9.1 μM; GI50, 16.6 μM).

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Synthesis of sulfonamides bearing 1,3,5-triarylpyrazoline and 4-thiazolidinone moieties as novel antimicrobial agents

Journal of the Serbian Chemical Society ◽

10.2298/jsc180621057t ◽

2020 ◽

Vol 85 (2) ◽

pp. 155-162

Author(s):

Thi-Dan Thach ◽

Thi Le ◽

Thien-Annguyen Nguyen ◽

Chi-Hien Dang ◽

Van-Su Dang ◽

...

Keyword(s):

Antimicrobial Agents ◽

Antimicrobial Activities ◽

Significant Inhibition ◽

Mercaptoacetic Acid ◽

Bacterial Strains ◽

Reference Drug ◽

E Coli ◽

Yeast Strains ◽

Microbial Strains

Two series of sulfonamides were synthesized from 4-hydrazinylbenzenesulfonamide as the key starting material. 1,3,5-Triarylpyrazoline sulfonamides (2a?i) were obtained by cyclocondensation of various chalcones in 53? ?64 % yields, while 4-thiazolidinone derivatives (4a?e) were synthesized by cyclocondensation between mercaptoacetic acid and different phenylhydrazones in 43?62 % yields. The synthesized compounds were characterized based on FTIR, 1H-NMR, 13C-NMR and HRMS data. The sulfonamides were evaluated for their in vitro antimicrobial activities against four bacterial strains (E. coli, P. aeruginosa, B. subtillis and S aureus), two filamentous fungal strains (A. niger and F. oxysporum) and two yeast strains (C. albicans and S. cerevisiae). Seven pyrazolines, 2a?c and 2e?h, exhibited significant inhibition of different microbial strains. Among them, compound 2b displayed good antifungal activity against A. niger (MIC value at 12.5 ?g mL-1) over the reference drug.

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Synthesis and Biological Evaluation of Some Pyrazole Derivatives, Containing (Thio) Semicarbazide, as Dual Anti-Inflammatory Antimicrobial Agents

Letters in Drug Design & Discovery ◽

10.2174/1570180816666190325163117 ◽

2019 ◽

Vol 16 (9) ◽

pp. 1020-1030

Author(s):

Zhaochang Liang ◽

Yuping Huang ◽

Shiben Wang ◽

Xianqing Deng

Keyword(s):

Antiinflammatory Activity ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Dilution Method ◽

Pyrazole Derivatives ◽

Reference Drug ◽

Tnf Α ◽

Anti Inflammatory

Background: Several series of pyrazole derivatives containing (thio) semicarbazide (4a-4h, 5a-5l, 6a-6f, 7a-7c) were designed and synthesized to screen dual inflammatory and antimicrobial activities. Methods: The products were characterized by1H NMR, 13C NMR and HRMS. In vitro LPS-induced TNF-α model and in vivo xylene-induced ear-edema model were used to evaluate their antiinflammatory activity. Their in vitro antimicrobial activities were evaluated using a serial dilution method against several gram-positive strains, gram-negative strains and a fungi strain. Results: Bioassays indicated that most of the compounds markedly inhibited the expression of TNF- α at the concentration of 20 µg/mL Compounds 5i, 6b, and 7b had comparable in vivo antiinflammatory activity to the reference drug dexamethasone at the dose of 50 mg/kg. In addition, several compounds showed antimicrobial activity against different strains, and compounds 5g and 5h exhibited potent inhibitory activities with the MIC value of 8 µg/mL against the Streptococcus pneumoniae CMCC 31968 and Staphylococcus aureus CMCC 25923, respectively. Compound 7b, which exhibited both anti-inflammatory and antimicrobial activities, should be studied as it is or after derivatization. Conclusion: It can be concluded that pyrazoles, with (thio)-semicarbazone moieties, have the potential to be developed into new anti-inflammatory agents.

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Synthesis and Biological Evaluation of Flavonoids as Antiacetyl- cholinesterase Agent

Jurnal Teknologi ◽

10.11113/jt.v69.2588 ◽

2014 ◽

Vol 69 (1) ◽

Author(s):

Saleh Nazifi Ibrahim ◽

Farediah Ahmad

Keyword(s):

Thin Layer ◽

Thin Layer Chromatography ◽

Inhibitory Activity ◽

Biological Evaluation ◽

Microplate Assay ◽

Synthetic Compounds ◽

Ache Inhibitory Activity ◽

Weak Activity ◽

Layer Chromatography ◽

Synthesis And Biological Evaluation

A series of chalcones, a flavone and one flavanone were synthesized and elucidated structurally by IR and 1H NMR spectroscopies. The synthetic compounds were then screened for acetylcholinesterase inhibitory activity using thin layer chromatography (TLC) and microplate assays. In the TLC assay, only 2′-hydroxy-4-methoxychalcone and 2′-hydroxy-4′-O-prenyl-2,6-dichlorochalcone were found to show moderate and weak activity respectively against acetylcholinesterase (AchE) at 0.1 mM concentration compared to the control galanthamine. 4′-Hydroxy-2,6-dichlorochalcone, 2′-hydroxy-4-nitrochalcone, 2′-hydroxy-4-(dimethyl)aminochalcone and 2′-hydroxy-4-methoxychalcone showed moderate AchE inhibitory activity with percentage inhibition of 54.24, 46.14 and 49.32 % respectively in the microplate assay.

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Synthesis and Antimicrobial Evaluation of Amino Acid Naphthoquinone Derivatives as Potential Antibacterial Agents

Chemotherapy ◽

10.1159/000521098 ◽

2021 ◽

Author(s):

Lluvia Itzel López-López ◽

Ernesto Rivera-Ávalos ◽

Cecilia Villarreal-Reyes ◽

Fidel Martínez-Gutiérrez ◽

Denisse de Loera

Keyword(s):

Escherichia Coli ◽

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Amino Acid ◽

Antimicrobial Activities ◽

Biological Evaluation ◽

Culture Collection ◽

Anticancer Activities ◽

Broth Microdilution Method

Background: The synthesis and biological evaluation of 1,4-naphthoquinone derivatives are of great interest since these compounds exhibit strong antibacterial, antifungal, antimalarial, and anticancer activities. The electronic properties of naphthoquinones are usually modulated by attaching functional groups containing nitrogen, oxygen and sulfur atoms, which tune their biological potency and selectivity. Methods: A series of 13 amino acid 1,4-naphthoquinone derivatives were synthesized under assisted microwave and ultrasound conditions. The antibacterial activity compounds was tested against American type Culture Collection (ATCC): Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Enterococcus faecalis, as well two multidrug resistant pathogens: Escherichia coli and Staphylococcus aureus from clinical isolated. Minimal inhibitory concentration (MIC) was determined using the broth microdilution method. Results: MIC of derivatives 4–11, 14 and 16 showed antimicrobial activity against gram-positive and gram-negative bacteria. Antimicrobial activities of the compounds 4–8 and 14 were ≤MIC 24.7 μg∙mL-1 against all the reference strain, even more the compound 6 showed the most potent activity with a MIC of 3.9 μg∙mL-1 on S. aureus. On the clinical isolated the compounds 7, 8 and 14 showed a MIC of 49.7 and 24.7 μg∙mL-1 against S. aureus y E. coli respectively. About ADME properties and Osiris analysis, the compounds 4-16 presented high gastrointestinal absorption and good characteristics for oral bioavailability and the compound 14 was the less toxic. Conclusion: amino acid 1,4-naphthoquinone derivatives showed good in vitro antibacterial activity against clinical strains, and modifications on C-3 with cloride atom enhanced the efficiency against same pathogens.

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Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors

RSC Advances ◽

10.1039/c4ra08708a ◽

2014 ◽

Vol 4 (95) ◽

pp. 52702-52711 ◽

Cited By ~ 4

Author(s):

Ya-Juan Qin ◽

Man Xing ◽

Ya-Liang Zhang ◽

Jigar A. Makawana ◽

Ai-Qin Jiang ◽

...

Keyword(s):

Inhibitory Activity ◽

Biological Evaluation ◽

Methyl Benzoate ◽

Design Synthesis ◽

Synthesis And Biological Evaluation ◽

Potent Inhibitory Activity ◽

Benzoate Derivatives

A series of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives (6a–10d) were designed and synthesized and evaluated as BRAFV600 inhibitors. Among them, compound 10a showed the most potent inhibitory activity against A375, WM266.4 and BRAFV600Ein vitro with IC50 values of 1.36 μM, 0.94 μM and 0.11 μM, respectively.

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Synthesis and Biological Evaluation of Some New 1,2,3-Triazole Derivatives As Anti-microbial Agents

JOURNAL OF ADVANCES IN CHEMISTRY ◽

10.24297/jac.v11i2.2215 ◽

2016 ◽

Vol 11 (2) ◽

pp. 3473-3484

Author(s):

Bahaa Gamal Mohamed Youssif ◽

Mostafa H. Abdelrahman

Keyword(s):

Antifungal Activity ◽

High Resolution Mass Spectrometry ◽

Biological Evaluation ◽

Bacterial Strains ◽

Reference Drug ◽

1H And 13C Nmr ◽

Triazole Derivatives ◽

New Compounds ◽

Microbial Agents ◽

Synthesis And Biological Evaluation

A series of 1,2,3-triazole derivatives bearing different chemical entities were prepared starting from 2-(4-phenyl-1H-1,2,3-triazol-1-yl)acetohydrazide, compound 2. The purity of all new compounds was checked by TLC and elucidation of their structures was confirmed by IR, 1H and 13C NMR along with High Resolution Mass Spectrometry (HRMS). All the target compounds were evaluated for their possible antimicrobial activity. Most of the tested compounds showed moderate to good antibacterial activity against most of the bacterial strains used in comparison with ciprofloxacin as a reference drug. The most active compounds were 4a, 9a, 9b, and 9f. Results of antifungal activity revealed that most of the tested compounds showed a good antifungal activity in comparison to fluconazole as a reference drug. Compounds 4a, 9c, 9d and 9f were the most active ones.

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IDENTIFICATION OF THE ANTIBACTERIAL EFFICACY OF ETHANOLIC EXTRACTS FROM AGLAONEMA COMMUTATUM SCHOTT LEAVES AND ITS CULTIVARS AGAINST ESCHERICHIA COLI STRAIN

The Scientific and Technical Bulletin of the Institute of Animal Science NAAS of Ukraine ◽

10.32900/2312-8402-2020-123-21-30 ◽

2020 ◽

pp. 21-30

Author(s):

Maryna Opryshko ◽

Oleksandr Gyrenko ◽

Lyudmyla Buyun ◽

Halyna Tkachenko ◽

Natalia Kurhaluk ◽

...

Keyword(s):

Escherichia Coli ◽

Antibacterial Activity ◽

Inhibitory Activity ◽

Antimicrobial Activities ◽

Farm Animals ◽

Leaf Extracts ◽

Ethanolic Extracts ◽

Inhibition Zones ◽

In Vitro Inhibition

This study aimed to evaluate the antibacterial activity of ethanolic extracts obtained from the leaves of Aglaonema commutatum Schott and its cultivars («Malay Beauty», «Silver Queen», and «Silver King») against Escherichia coli (Migula) Castellani and Chalmers (ATCC® 25922™) strain. The leaves of Aglaonema commutatum plants and its cultivars, cultivated under glasshouse conditions, were sampled at M. M. Gryshko National Botanic Garden (NBG), National Academy of Science of Ukraine (Kyiv, Ukraine). The leaves were brought into the laboratory for antimicrobial studies. Freshly sampled leaves were washed, weighed, and homogenized in 96% ethanol (in proportion 1:19) at room temperature. The extracts were then filtered and investigated for their antimicrobial activity. Escherichia coli (Migula) Castellani and Chalmers (ATCC® 25922™) strain was used in our study. Antimicrobial activities of various ethanolic extracts obtained from leaves of Aglaonema commutatum plants and its cultivars («Malay Beauty», «Silver Queen», and «Silver King») against Escherichia coli (Migula) Castellani and Chalmers (ATCC® 25922™) strain was screened in the current study. The testing of the antibacterial activity of the plant extracts was carried out in vitro by the Kirby-Bauer disc diffusion technique. The leaf extracts from A. commutatum «Silver Queen» and A. commutatum 'Silver King' exhibited higher inhibitory activity than the extracts from A. commutatum and A. commutatum «Malay Beauty». Maximum in vitro inhibition was scored by A. commutatum «Silver Queen», followed by A. commutatum «Silver King», A. commutatum, and A. commutatum «Malay Beauty». In particular, the leaf extracts from A. commutatum «Silver Queen» and A. commutatum 'Silver King' exhibited higher inhibitory activity than the extracts from A. commutatum and A. commutatum «Malay Beauty». Maximum in vitro inhibition was scored by A. commutatum «Silver Queen», followed by A. commutatum «Silver King», A. commutatum, and A. commutatum «Malay Beauty», which presented inhibition zones of (18.6±1.2) mm, (16.1±0.9) mm, (15.7±1.1) mm, and (13.5±1.0) mm, respectively. In the case of the positive controls, 96% ethanol possesses a mild anti-E. coli effect, which presented inhibition zones of (9.5±1.2) mm. The inhibition zone diameters were increased by 96% (p<0.05) for A. commutatum «Silver Queen», by 69 % (p<0.05) for A. commutatum «Silver King», by 65 % (p<0.05) for A. commutatum, and by 42 % (p<0.05) for A. commutatum «Malay Beauty». Thus, the use of these plants in traditional medicine and veterinary medicine was experimentally confirmed as a potential source of raw materials for the development of medicines in the future, as well as for the development of innovative feed for farm animals.

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Synthesis and biological evaluation of some new 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines as antimicrobial agents

Current Chemistry Letters ◽

10.5267/j.ccl.2021.9.003 ◽

2022 ◽

Vol 11 (1) ◽

pp. 75-82 ◽

Cited By ~ 1

Author(s):

Iryna Myrko ◽

Taras Chaban ◽

Vasyl Matiychuk

Keyword(s):

Mass Spectrometry ◽

Escherichia Coli ◽

Staphylococcus Aureus ◽

Pseudomonas Aeruginosa ◽

Antimicrobial Activity ◽

Antibacterial Activity ◽

Antimicrobial Agents ◽

Biological Evaluation ◽

Bacterial Strains ◽

Synthesis And Biological Evaluation

A series of some new pyrazole-substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines was synthesized in this study. The structures of target substances were confirmed by using 1H and 13С NMR spectroscopy, mass spectrometry and elemental analysis. The synthesized compounds have been evaluated for antimicrobial activity against five bacterial strains (Escherichia coli, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, Staphylococcus aureus) and two fungal strains (Candida albicans and Cryptococcus neoformans). The antimicrobial screening studies of synthesized substances established that 2 of 12 compounds show pronounced antibacterial activity against the strain Staphylococcus aureus.

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