scholarly journals Design, Synthesis and Antifungal Activity of Novel Benzoylcarbamates Bearing a Pyridine Moiety

2018 ◽  
Vol 8 (12) ◽  
pp. 2577
Author(s):  
Fu-Xian Wan ◽  
Jian-Hua Wang ◽  
Yan-Hua Shi ◽  
Li-Zhi Niu ◽  
Lin Jiang
Keyword(s):  
Antifungal Activity ◽  
High Efficiency ◽  
Plant Diseases ◽  
Moderate Activity ◽  
Significant Activity ◽  
Environmental Friendliness ◽  
Design Synthesis ◽  
Lead Compounds ◽  
Pyridine Moiety

Many natural and synthetic pyridine derivatives have good biological activity, and are widely used in the fields of pesticides and medicines. On the other hand, carbamate fungicides possess some unique properties, such as high efficiency, strong selectivity, low toxicity, and environmental friendliness, and are often used to control many plant diseases. Therefore, discovering novel pyridine-based carbamates is of great significance. In this paper, we chose the excellent fungicides tolprocarb and picarbutrazox as lead compounds, integrating benzoyl, carbamate, and pyridinyl moieties into a molecule. Thus, we designed and synthesized a series of substituted benzoyl carbamates containing a pyridine ring, and evaluated the in vitro antifungal activity. The target compounds exhibited moderate to strong bioactivity against Botrytis cinerea, among which the compounds 4d, 4f, 4g, and 4h exhibited significant activity with EC50 values (the concentration resulting in a 50% inhibition) of 6.45–6.98 μg/mL, and their activities were near or superior to that of chlorothalonil. Additionally, 4h exhibited moderate activity against Sclerotinia sclerotiorumwith an EC50 value of 10.85 μg/mL.

Design, Synthesis and Antibacterial, Antifungal Activity of Some Coumarin Acetohydrazide Derivatives

2021 ◽  
pp. 3931-3937
Author(s):  
A. R. Chabukswar ◽  
P.V. Adsule ◽  
P.B. Randhave ◽  
Manini Mantri
Keyword(s):  
Antifungal Activity ◽  
Moderate Activity ◽  
Gram Negative Bacteria ◽  
Significant Activity ◽  
Design Synthesis ◽  
E Coli ◽  
Gram Positive Bacteria ◽  
Antibacterial And Antifungal ◽  
Gyrase Inhibitors

We have designed and synthesized (Z)-2-(5-methyl-2-oxo-2H-chromen-7-yl) oxy)-N’-(2-oxoindolin-3-ylidin) acetohydrazide derivatives by reacting 7-hydroxy-4-methyl-coumarin and substituted isatin to afford 12 substituted coumarin acetohydrazide derivatives. The synthesized compounds of coumarin acetohydrazide derivatives were designed and evaluated to study for their possible interactions as DNA gyrase inhibitors. All the synthesized coumarin acetohydrazide compounds have been characterized by spectral analysis IR, 1H NMR and mass spectroscopy. The compounds have been evaluated for In vitro antibacterial and antifungal activity against S. aureus, B. subtilus, E. coli, P. aeruginosa and fungi C. albicans and A. niger. In case of Gram positive bacteria and Gram negative bacteria Compound P5C, M5C, C5C exhibited significant activity. Compounds P5N, M5N, C5N shown moderate activity. Compound P5C, M5C, C5C shown significant Antifungal activity against C. albicans and A. niger. Compounds P5C, M5C, C5C are found to exert significant antibacterial as well as antifungal activity and can serve as potential compound against infectious diseases in future.

Novel 2-(5-Aryl)thiophen-2-yl)benzimidazoles; Design, Synthesis and In vitro Evaluation Against Cercarial Phase of Schistosoma mansoni

2020 ◽  
Vol 17 (11) ◽  
pp. 1432-1438
Author(s):  
Serry Atta El Bialy ◽  
Basem Mansour ◽  
Waleed Abdelhakeem Bayoumi ◽  
Amira Taman ◽  
Hassan Mohammed Eissa
Keyword(s):  
Structural Modification ◽  
Anthelmintic Activity ◽  
Ring System ◽  
Literature Survey ◽  
Moderate Activity ◽  
Significant Activity ◽  
Design Synthesis ◽  
Interesting Class ◽  
Low Activity

Background: Literature survey has pointed out that Benzimidazoles represent an interesting class of anthelmintics, of which several potent members were developed. Objective: Benzimidazoles hybridized with pharmacophoric moieties possessing anthelmintic activity were designed, synthesized to be evaluated against cercaria. Methods: Structural modification was achieved through 2- and 5-positions. Moreover, an in vitro cercarial assay was adopted to evaluate target compounds. Results and Discussion: Biological screening revealed that compound 3h showed significant activity with a survival index of 35% at a 100 μg/mL concentration. Whereas, compounds 3a and 3c showed moderate activity, the rest of the tested compounds exhibited low activity. Conclusion: The current study evidenced that the new hybrids "benzimidazole-thiophen-aryl" are successful as cercacidal agents. Further studies of this novel tri-ring system are suggested on adult worms of S. mansoni.

scholarly journals Design, Synthesis and Antifungal Activity of New Schiff Bases Bearing 2-Aminothiophene Derivatives Obtained by Molecular Simplification

2021 ◽  
Author(s):  
Isadora Luna ◽  
Wendell Neves ◽  
Reginaldo de Lima-Neto ◽  
Amanda Albuquerque ◽  
Maíra Pitta ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Schiff Bases ◽  
Antifungal Drugs ◽  
Microwave Assisted Synthesis ◽  
Design Synthesis ◽  
Reference Drug ◽  
Lead Compounds ◽  
Pharmacokinetic Properties ◽  
In Vitro Antifungal Activity

Seventeen Schiff bases bearing 2-aminothiophene derivatives were designed and synthesized using molecular simplification. The resulting compounds (4a-4q) were evaluated for their in vitro antifungal activity against dermatophytes. Prediction of their druglikeness and pharmacokinetic properties, establishment of their structure-activity relationships (SAR), and cytotoxic evaluation of the most active compounds were performed. Using an eco-friendly procedure, microwave assisted synthesis resulted in compounds in good yields (35-85%). Compounds 4a-4q presented good druglikeness and pharmacokinetic profiles and no cytotoxicity for any cell line tested up to 100 μM. The compounds presenting the best antifungal profiles were 4e, 4f, 4g, 4k, 4l, 4m, 4o and 4p with more than one minimum inhibitory concentration (MIC) value occurring between 16‑64 μg mL-1, thus, in some cases better than the reference drug (fluconazole). SAR testing indicated that the presence of halogens and nitro substituents increases antifungal activity. Taken together, the results demonstrate that 2-aminothiophene derivatives are promising lead compounds for the development of antifungal drugs.

Design, Synthesis and Evaluate In Vitro Antifungal Activity of Novel Benzamide Derivatives

2019 ◽  
Vol 41 (3) ◽  
pp. 549-549
Author(s):  
Xuesong Wang and Xiaorong Tang Xuesong Wang and Xiaorong Tang
Keyword(s):  
Antifungal Activity ◽  
Pathogenic Fungi ◽  
Gibberella Zeae ◽  
Design Synthesis ◽  
Carboxylic Acid Amides ◽  
Almost All ◽  
Negative Controls ◽  
New Compounds ◽  
Benzamide Derivatives

A series of novel benzamide derivatives according to fluopicolide were designed and synthesized following the rule of combination carboxylic acid amides and amines derivatives together. The antifungal activity of the 15 new compounds were evaluated in vitro against five pathogenic fungi, including Sclerotinia sclerotiorum, Gibberella zeae, Rhizoctonia solani, Helminthosporium maydis and Botrytis cinerea. Almost all the structure have not been reported, except compounds 3, 5 and 6. A surprising finding is that all the five tested fungi breed faster than negative controls when supplementary with compound 715 , respectively.

Exploring the potential of imines as antiprotozoan agents with focus on t. Brucei and p. Falciparum

2018 ◽  
Author(s):  
◽  
Kola Augustus Oluwafemi
Keyword(s):  
Hela Cell ◽  
Cell Line ◽  
Special Focus ◽  
Hela Cell Line ◽  
Free Energies ◽  
Imino Group ◽  
Design Synthesis ◽  
Lead Compounds ◽  
Pyridine Moiety ◽  
Nmr Study

This work focuses on the design, synthesis and evaluation of imine-containing heterocyclic and acyclic compounds with special focus on their bioactivity against parasitic protozoans (P. falciparum and T. brucei) - given the context of drug resistance in the treatment of malaria and Human African sleeping sickness and the fact that several bioactive organic compounds have been reported to possess the imino group. Starting from 2-aminopyridine, novel #-alkylated-5-bromo-7-azabenzimidazoles and substituted 5-bromo-1-(carbamoylmethy)-7-azabenzimidazole derivatives were prepared, and their bioactivity against parasitic protozoans was assessed. NMR spectra of the substituted 5- bromo-1-(carbamoylmethy)-7-azabenzimidazole derivatives exhibited rotational isomerism, and a dynamic NMR study was used in the estimation of the rate constants and the free- energies of activation for rotation. The free-energy differences between the two rotamers were determined and the more stable conformations were predicted. Novel 2-phenyl-7-azabenzimidazoles were also synthesised from 2-aminopyridine. A convenient method for the regioselective formylation of 2,3-diaminopyridines into 2-amino- 7-(benzylimino)pyridine analogues of 2-phenyl-7-azabenzimidazole was developed, and some of the resulting imino derivatives were hydrogenated to verify the importance of the imino moiety for bioactivity. The 2-phenyl-7-azabenzimidazoles and the 2-amino-7- (benzylimino)pyridine analogues were screened for their anti-protozoal activity and their cytotoxicity level was determined against the HeLa cell line. In order to validate the importance of the pyridine moiety, novel #-(phenyl)-2- hydroxybenzylimines, #-(benzyl)-2-hydroxybenzylimines and (±)-trans-1,2-bis[2- hydroxybenzylimino]cyclohexanes were also synthesized and screened for activity against the parasitic protozoans and for cytotoxicity against the HeLa cell line. The biological assay results indicated that these compounds are not significantly cytotoxic and a good number of them show potential as lead compounds for the development of new malaria and trypanosomiasis drugs.

scholarly journals Design, Synthesis and Biological Evaluation of Novel 1, 3, 4-Oxadiazole Bearing Pyridine Moiety

2019 ◽  
pp. 300-307
Author(s):  
Asma D. Ambekari ◽  
Shrinivas K. Mohite
Keyword(s):  
Antimicrobial Activity ◽  
Mass Spectra ◽  
Biological Evaluation ◽  
Design Synthesis ◽  
Pyridine Moiety ◽  
Anti Inflammatory ◽  
Physicochemical Data ◽  
Synthesis And Biological Evaluation

Series of novel substituted Synthesis of N-{[5-(substituted)-1,3,4-oxadiazole-2-yl] carbamothioyl} derivatives containing 1,3,4-oxadiazole moiety were synthesized by microwave as a green chemistry method and conventional method by using pyridine 3- carboxylic acid as a starting material. The structures of the synthesized compounds were characterized by physicochemical data, IR, Mass spectra and 1HNMR. All the newly synthesized compound screened for their antimicrobial and In-vivo and In-vitro Anti-inflammatory studies. Anti-inflammatory studies revealed that compound 4f showed significant in-vivo and in-vitro anti-inflammatory activity as well potent antimicrobial activity.

scholarly journals Chloroquine Urea Derivatives: Synthesis and Antitumor Activity in Vitro

2018 ◽  
Vol 68 (4) ◽  
pp. 471-483 ◽  
Author(s):  
Kristina Pavić ◽  
Zrinka Rajić ◽  
Zvonimir Mlinarić ◽  
Lidija Uzelac ◽  
Marijeta Kralj ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Anticancer Agents ◽  
Human Cancer ◽  
Human Cancer Cell ◽  
Urea Derivatives ◽  
Design Synthesis ◽  
Human Cancer Cell Lines ◽  
Lead Compounds ◽  
Insight Into

Abstract In the current paper, we describe the design, synthesis and antiproliferative screening of novel chloroquine derivatives with a quinoline core linked to a hydroxy or halogen amine through a flexible aminobutyl chain and urea spacer. Synthetic pathway leading to chloroquine urea derivatives 4-10 includes two crucial steps: i) synthesis of chloroquine benzotriazolide 3 and ii) formation of urea derivatives through the reaction of compound 3 with the corresponding amine. Testing of antiproliferative activity against four human cancer cell lines revealed that chloroquine urea derivatives 9 and 10 with aromatic moieties show activity at micromolar concentrations. Therefore, these molecules represent interesting lead compounds that might provide an insight into the design of new anticancer agents.

scholarly journals Design, Synthesis and Fungicidal Activity of New 1,2,4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety

Molecules ◽  
2020 ◽  
Vol 25 (24) ◽  
pp. 5852
Author(s):  
Hui Bai ◽  
Xuelian Liu ◽  
Pengfei Chenzhang ◽  
Yumei Xiao ◽  
Bin Fu ◽  
...  
Keyword(s):  
High Resolution Mass Spectrometry ◽  
Binding Modes ◽  
Oxime Ether ◽  
Single Crystal Diffraction ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Triazole Derivatives ◽  
Pyridine Moiety ◽  
New Compounds

A series of novel 1,2,4-triazole derivatives containing oxime ether and phenoxy pyridine moiety were designed and synthesized. The new compounds were identified by nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectrometry (HRMS). Compound (Z)-1-(6-(4-nitrophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a18) was further confirmed by X-ray single crystal diffraction. Their antifungal activities were evaluated against eight phytopathogens. The in vitro bioassays indicated that most of the title compounds displayed moderate to high fungicidal activities. Compound (Z)-1-(6-(4-bromo-2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-methyl oxime (5a4) exhibited a broad-spectrum antifungal activities with the EC50 values of 1.59, 0.46, 0.27 and 11.39 mg/L against S. sclerotiorum, P. infestans, R. solani and B. cinerea, respectively. Compound (Z)-1-(6-(2-chlorophenoxy)pyridin-3-yl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one O-benzyl oxime (5b2) provided the lowest EC50 value of 0.12 mg/L against S. sclerotiorum, which were comparable to the commercialized difenoconazole. Moreover, homologous modeling and molecular docking disclosed possible binding modes of compounds 5a4 and 5b2 with CYP51. This work provided useful guidance for the discovery of new 1,2,4-triazole fungicides.

scholarly journals Antifungal Activity of Silver Ions and Nanoparticles on Phytopathogenic Fungi

Plant Disease ◽  
2009 ◽  
Vol 93 (10) ◽  
pp. 1037-1043 ◽  
Author(s):  
Young-Ki Jo ◽  
Byung H. Kim ◽  
Geunhwa Jung
Keyword(s):  
Antifungal Activity ◽  
Colony Formation ◽  
Magnaporthe Grisea ◽  
Silver Ions ◽  
Pathogenic Fungi ◽  
Chloride Ions ◽  
Plant Diseases ◽  
Plant Pathogenic Fungi ◽  
In Planta

Silver in ionic or nanoparticle forms has a high antimicrobial activity and is therefore widely used for various sterilization purposes including materials of medical devices and water sanitization. There have been relatively few studies on the applicability of silver to control plant diseases. Various forms of silver ions and nanoparticles were tested in the current study to examine the antifungal activity on two plant-pathogenic fungi, Bipolaris sorokiniana and Magnaporthe grisea. In vitro petri dish assays indicated that silver ions and nanoparticles had a significant effect on the colony formation of these two pathogens. Effective concentrations of the silver compounds inhibiting colony formation by 50% (EC50) were higher for B. sorokiniana than for M. grisea. The inhibitory effect on colony formation significantly diminished after silver cations were neutralized with chloride ions. Growth chamber inoculation assays further confirmed that both ionic and nanoparticle silver significantly reduced these two fungal diseases on perennial ryegrass (Lolium perenne). Particularly, silver ions and nanoparticles effectively reduced disease severity with an application at 3 h before spore inoculation, but their efficacy significantly diminished when applied at 24 h after inoculation. The in vitro and in planta evaluations of silver indicated that both silver ions and nanoparticles influence colony formation of spores and disease progress of plant-pathogenic fungi. In planta efficacy of silver ions and nanoparticles is much greater with preventative application, which may promote the direct contact of silver with spores and germ tubes, and inhibit their viability.

scholarly journals Design, synthesis and biological evaluation of novel benzodioxole derivatives as COX inhibitors and cytotoxic agents

BMC Chemistry ◽  
2020 ◽  
Vol 14 (1) ◽  
Author(s):  
Mohammed Hawash ◽  
Nidal Jaradat ◽  
Saba Hameedi ◽  
Ahmed Mousa
Keyword(s):  
Cancer Cell Line ◽  
Biological Evaluation ◽  
Cytotoxic Agents ◽  
Cervical Cancer Cell Line ◽  
Moderate Activity ◽  
Selectivity Ratio ◽  
Design Synthesis ◽  
Cox Inhibitors ◽  
Cytotoxic Compound

Abstract Non-steroidal anti-inflammatory drugs are among the most used drugs. They are competitive inhibitors of cyclooxygenase (COX). Twelve novel compounds (aryl acetate and aryl acetic acid groups) were synthesized in this work in order to identify which one was the most potent and which group was most selective towards COX1 and COX2 by using an in vitro COX inhibition assay kit. The cytotoxicity was evaluated for these compounds utilizing MTS assay against cervical carcinoma cells line (HeLa). The synthesized compounds were identified using FTIR, HRMS, 1H-NMR, and 13C-NMR techniques. The results showed that the most potent compound against the COX1 enzyme was 4f with IC50 = 0.725 µM. The compound 3b showed potent activity against both COX1 and COX2 with IC50 = 1.12 and 1.3 µM, respectively, and its selectivity ratio (0.862) was found to be better than Ketoprofen (0.196). In contrast, compound 4d was the most selective with a COX1/COX2 ratio value of 1.809 in comparison with the Ketoprofen ratio. All compounds showed cytotoxic activity against the HeLa Cervical cancer cell line at a higher concentration ranges (0.219–1.94 mM), and the most cytotoxic compound was 3e with a CC50 value of 219 µM. This was tenfold more than its IC50 values of 2.36 and 2.73 µM against COX1 and COX2, respectively. In general, the synthesized library has moderate activity against both enzymes (i.e., COX1 and COX2) and ortho halogenated compounds were more potent than the meta ones.

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