Design, Synthesis and Antifungal Activity of Novel 1-(Adamantan-1-yl) ethanone Oxime Esters

2020 ◽  
Vol 17 (5) ◽  
pp. 526-532
Author(s):  
Si Liu ◽  
Li-Zhi Niu ◽  
Yan-Hua Shi ◽  
Fu-Xian Wan ◽  
Lin Jiang
Keyword(s):  
Antifungal Activity ◽  
Biological Activities ◽  
Lead Compound ◽  
Design Synthesis ◽  
Antifungal Activities

Background: Oxime compounds, including oxime ethers and oxime esters, possess various biological activities. Many oxime ethers have been widely used in the fields of pesticides and medicines. However, oxime ethers are rarely used in the field of pesticides. Methods: We chose the excellent fungicide pyrifenox as the lead compound, integrated pyridinyl, adamantyl and benzoyl moieties into one molecule, while also designed and synthesized ten 1- (adamantan-1-yl)ethanone oxime esters containing pyridinyl moiety. Moreover, we also evaluated their preliminary antifungal activities against S. sclerotiorum and B. cinerea. Results: The target compounds were characterized by NMR, IR and HRMS. The preliminary bioactivity test showed that they exhibited some antifungal activity to S. sclerotiorum and B. cinerea, and EC50 values were in the range of 14.16-32.97 and 27.60-52.82 μg/mL, respectively. Conclusion: Some target compounds such as 3d, 3e, 3h and 3i, exhibited moderate activities against S. sclerotiorum, with EC50 values of 14.16-18.18 μg/mL.

Antioxidant and antifungal activities of Myrianthus arboreus P. Beauv. (Moraceae), Allanblackia gabonensis Pellegr. (Clusiaceae) and three other Cameroonian medicinal plants

2021 ◽  
Vol 4 (1) ◽  
pp. 1-7
Author(s):  
Aimé G. Fankam ◽  
Serge S. Atsafack ◽  
Guy S. S. Njateng ◽  
Jules R. Kuiate
Keyword(s):  
Antioxidant Activity ◽  
Antifungal Activity ◽  
Medicinal Plants ◽  
Biological Activities ◽  
Radical Scavenging ◽  
Reducing Power ◽  
Bark Extract ◽  
Total Phenolic ◽  
Antifungal Activities ◽  
Allanblackia Gabonensis

Background: Biological activities of medicinal plants make them attractive alternative complementary medicines. Therefore, this study aimed to assess the antioxidant and antifungal activities of the methanol extract of Myrianthus arboreus, Allanblackia gabonensis, Gladiolus quartinianus, Peperomia fernandopoiana and Vepris soyauxii. Methods: Total phenolic contents (TPC) and flavonoid contents (FC) were evaluated using standard methods. The antioxidant activity of the extracts was determined by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging and ferric reducing power assays. Antifungal activity was evaluated by the broth micro-dilution method. Results: TPC of extracts ranging from 67.89 to 196.01 mgGAE/g TPC were very higher in P. fernandopoiana whole plant (PFW) extract (196.01±10.25 mgGAE/g) and MAL (165.71±10.68 mgGAE/g) whereas the A. gabonensis fruit extract (AGF) and M. arboreus bark extract (MAB) had the highest flavonoid content (66.54 ± 2.12 and 48.13 ± 1.65 mgEC/g of extract, respectively). Apart from M. arboreus leave extract (MAL), all extracts showed important DPPH radical scavenging activity (IC50 < 20 μg/mL). AGFl and PFW exhibited significant ferric reducing power compared to ascorbic acid and other extracts (P<0.05). Each of the tested extracts showed antifungal activity against atleast one of the five pathogenic fungi, with MICs ranging from 128 to 1024 µg/mL. MAL was active on all the tested fungi whereas MAB showed the highest antifungal activity (MIC=128 µg/mL). Conclusion: The findings of this study emphasize the evidence that the methanol extracts of the leave and bark of Myrianthus arboreus could be an alternative to fight against oxidative stresses and infections due to opportunistic yeast pathogens. Keywords: Oxidative stress; fungal infection; medicinal plant; antioxidant activity; antifungal activity.

scholarly journals Novel Fluorinated 7-Hydroxycoumarin Derivatives Containing an Oxime Ether Moiety: Design, Synthesis, Crystal Structure and Biological Evaluation

Molecules ◽  
2021 ◽  
Vol 26 (2) ◽  
pp. 372
Author(s):  
Qing-Qing Wang ◽  
Shu-Guang Zhang ◽  
Jian Jiao ◽  
Peng Dai ◽  
Wei-Hua Zhang
Keyword(s):  
Antifungal Activity ◽  
Positive Control ◽  
Biological Evaluation ◽  
Gibberella Zeae ◽  
X Ray Diffraction ◽  
Oxime Ether ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Better Than

A series of fluorinated 7-hydroxycoumarin derivatives containing an oxime ether moiety have been designed, synthesized and evaluated for their antifungal activity. All the target compounds were determined by 1H-NMR, 13C-NMR, FTIR and HR-MS spectra. The single-crystal structures of compounds 4e, 4h, 5h and 6c were further confirmed using X-ray diffraction. The antifungal activities against Botrytis cinerea (B. cinerea), Alternariasolani (A. solani), Gibberella zeae (G. zeae), Rhizoctorzia solani (R. solani), Colletotrichum orbiculare (C. orbiculare) and Alternaria alternata (A. alternata) were evaluated in vitro. The preliminary bioassays showed that some of the designed compounds displayed the promising antifungal activities against the above tested fungi. Strikingly, the target compounds 5f and 6h exhibited outstanding antifungal activity against B. cinerea at 100 μg/mL, with the corresponding inhibition rates reached 90.1 and 85.0%, which were better than the positive control Osthole (83.6%) and Azoxystrobin (46.5%). The compound 5f was identified as the promising fungicide candidate against B. cinerea with the EC50 values of 5.75 μg/mL, which was obviously better than Osthole (33.20 μg/mL) and Azoxystrobin (64.95 μg/mL). Meanwhile, the compound 5f showed remarkable antifungal activities against R. solani with the EC50 values of 28.96 μg/mL, which was better than Osthole (67.18 μg/mL) and equivalent to Azoxystrobin (21.34 μg/mL). The results provide a significant foundation for the search of novel fluorinated 7-hydroxycoumarin derivatives with good antifungal activity.

scholarly journals Design, Synthesis and Antimicrobial Evaluations of Novel 3,7-Disubstituted 2H-1-Benzopyran-2-ones

2020 ◽  
Vol 32 (9) ◽  
pp. 2397-2402
Author(s):  
PARMESH K. DWIVEDI ◽  
ASHUTOSH PATHAK ◽  
P. MALAIRAJAN ◽  
DEVDUTT CHATURVEDI
Keyword(s):  
Antifungal Activity ◽  
Phenyl Ring ◽  
Trichophyton Mentagrophytes ◽  
Side Chain ◽  
Design Synthesis ◽  
Antifungal Activities ◽  
Coumarin Ring

In present study, a novel class of 3,7-disubstituted 2H-1-benzopyran-2-one derivatives (3xa-3zc) bearing a basic ether side chain at C-7 and a substituted phenyl ring at C-3 of the coumarin ring is synthesized. These compounds have been evaluated for antimicrobial (antibacterial/antifungal) activities. Some of the compounds viz. 3xc, 3xe, 3xf, 3yb, 3yc and 3yf have shown significant antifungal activities against selective strains. Compounds 3xe, 3yb and 3yc with the MIC values of 1.56 μg/mL displayed better antifungal activity than fluconazole against Trichophyton mentagrophytes

scholarly journals DESIGN, SYNTHESIS AND ANTIMICROBIAL STUDIES OF 5-BENZYLIDENE SUBSTITUTED RHODANINE CONTAINING HETEROCYCLES

2021 ◽  
pp. 28-34
Author(s):  
CICI MATHEW ◽  
BINDU SARASWATI ◽  
NAND LAL ◽  
JOYAMMA VARKEY
Keyword(s):  
Antibacterial Activity ◽  
Antifungal Activity ◽  
Candida Tropicalis ◽  
Candida Glabrata ◽  
Antimicrobial Agents ◽  
Biological Activities ◽  
Antimicrobial Activities ◽  
Design Synthesis ◽  
Drug Candidates ◽  
Antimicrobial Studies

Objective: The principal objective of the study was to synthesize and evaluate the biological activities of a novel class of 5-benzylidene substituted rhodanine derivatives as antimicrobial agents. Methods: All the synthesized compounds (D1-D10) were screened for their antimicrobial activities using microdilution methods as per the reported procedure. All compounds were evaluated as potential antimicrobial agents against gram-positive bacteria: Bacillus cereus, Staphylococcus aureus, gram negative bacteria: Escherichia coli Pseudomonas aeruginosa and Klebsiella pneumoniae Fungal cultures used in the study were Aspergillus niger, Candida albicans, Candida parapsilosis, Candida tropicalis and Candida glabrata. Results: Compound D6 showed good antifungal activity in the MIC range 16μg/ml against Candida tropicalis and Compound D10 showed good antifungal activity in the MIC range 16μg/ml against Candida glabrata. Compounds D2 and D5 showed good antibacterial activity at 32μg/ml. all the other compounds showed moderate antibacterial activity. Conclusion: Based on the above results, it can be concluded that the compounds may lead to the development of more potent antimicrobial drug candidates in the near future.

Design, Synthesis, Anti-Proliferative Evaluation and Cell Cycle Analysis of Hybrid 2-Quinolones

2019 ◽  
Vol 19 (9) ◽  
pp. 1132-1140
Author(s):  
Heba A.E. Mohamed ◽  
Hossa F. Al-Shareef
Keyword(s):  
Cell Cycle ◽  
Anticancer Agents ◽  
Biological Activities ◽  
Flow Cytometric Analysis ◽  
Annexin V ◽  
Cytotoxic Activities ◽  
Significant Group ◽  
Design Synthesis ◽  
Standard Drug ◽  
Wide Range

Background: Quinolones are a significant group of nitrogen heterocyclic compounds that exist in therapeutic agents, alkaloids, and synthetic small molecules that have important biological activities. A wide range of quinolones have been used as antituberculosis, antibacterial, anti-malarial, antifungal, anticonvulsant, anticancer agents and urease inhibitors. Methods: Ethyl 3,3-disubstituted-2-cyano propionates containing hybride quinolones derivatives were synthesized by the reaction of 1-amino-7-hydroxy-4-methylquinolin-2(1H)-one and its dibromo derivative with α, β-unsaturated carbonyl in ethanol. Results: A novel series of hybrid 2-quinolone derivatives was designed and synthesized. The compounds structures were confirmed using different spectroscopic methods and elemental analysis. The cytotoxic activities of all the compounds were assessed against HepG2 cell line in comparison with doxorubicin as a standard drug. Conclusion: Most compounds revealed superior anti-proliferative activity than the standard. Compound 4b, is the most active compound (IC50 = 0.39mM) compared with doxorubicin (IC50 = 9.23mM). DNA flow cytometric analysis of compound 4b showed cell cycle arrest at G2/M phase with a concomitant increase of cells in apoptotic phase. Dual annexin-V/ propidium iodide staining assay of compound 4b revealed that the selected candidate increased the apoptosis of HepG-2 cells more than control.

Biological Activities of Carlina Oxide Isolated from the Roots of Carthamus caeruleus

2020 ◽  
Vol 10 (2) ◽  
pp. 145-152 ◽  
Author(s):  
Imane Rihab Mami ◽  
Rania Belabbes ◽  
Mohammed El Amine Dib ◽  
Boufeldja Tabti ◽  
Jean Costa ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Essential Oil ◽  
Skin Diseases ◽  
Antioxidant Activities ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Penicillium Expansum ◽  
Natural Food ◽  
Antioxidant Power

Background: Carthamus caeruleus belongs to the Asteraceae family. The roots are traditionally used as healing agents. They help to heal burns and treat skin diseases. They are also used against joint inflammation and are very effective against diseases such as irritable bowel syndrome for cancer patients. Objectives: The purpose of this work was i) to study the chemical composition of i) the essential oil and hydrosol extract of Carthamus caeruleus, ii) to isolate the major component of both extracts and iii) to evaluate their antioxidant, antifungal and insecticidal activities. Methods: The essential oil and hydrosol extract obtained from the roots were studied by GC and GC/MS. The antioxidant activities were performed using two different methods i) Radical scavenging activity (DPPH) and ii) the Ferric-Reducing Antioxidant Power (FRAP), using BHT as a positive control. Whereas, the antifungal activity of the essential oil and Carlina oxide was investigated against plant fungi. The fumigation toxicity of C. caeruleus essential oil besides Carlina oxide was evaluated against adults of Bactrocera oleae better known as the olive fly. Results: The essential oil and hydrosol extract were mainly represented by acetylenic compounds such as carline oxide and 13-methoxy carline oxide. Carlina oxide was isolated and identified by 1H and 13C NMR spectroscopic means. The results showed that Carlina oxide presented interesting antioxidant and antifungal properties, while C. caeruleus root essential oil had better insecticidal activity. Furthermore, Carlina oxide has demonstrated promising in vivo antifungal activity to control infection of apples by Penicillium expansum. Conclusion: Carlina oxide can be used as a natural food preservative and alternative to chemical fungicides to protect stored apple against Penicillium expansum.

Phytochemical Constituents of Tulbaghia violacea Harv Extract and its Antifungal Potential Against Cryptococcus neoformans and Cryptococcus gattii

2019 ◽  
Vol 9 (4) ◽  
pp. 330-340
Author(s):  
Mitradev Pattoo ◽  
Vuyokazi Belewa ◽  
Benesh Munilal Somai
Keyword(s):  
Antifungal Activity ◽  
Cryptococcus Neoformans ◽  
Antifungal Therapy ◽  
Developing World ◽  
Chemical Constituents ◽  
Cryptococcus Gattii ◽  
Plant Part ◽  
Aqueous Extracts ◽  
Antifungal Activities ◽  
Antifungal Potential

Background:In both the developed and developing world, the mortality rates of people afflicted with cryptococcosis are unacceptably high despite the availability of antifungal therapy. The disease is caused by Cryptococcus neoformans (predominantly in immunocompromised individuals) and by Cryptococcus gattii. Globally the disease is estimated to cause around 600,000 deaths annually. Antifungal therapy is available, but in the developing world, may be unaffordable to many people, there is an increasing threat of resistance to the available drugs and our repertoire of antifungal drugs is very limited. Consequently, more research has been focusing on the use of medicinal plants as therapeutic agents. The originality of the current study is that although Tulbaghia violacea is a well-documented medicinal plant, the chemical composition of aqueous extracts and their antifungal potential against pathogenic yeasts are unknown. This is the first study that evaluates the chemical constituents of aqueous T. violacea root, leaf, rhizome and tuber extracts and their corresponding antifungal activities against C. neoformans and C. gattii.Objectives:The study aimed to investigate the phytochemical composition and antifungal potential of Tulbaghia violacea root, leaf, rhizome and tuber extracts against Cryptococcus neoformans and Cryptococcus gattii.Methods:Roots, leaves, rhizomes and tubers were extracted with water only for 48 h at room temperature with continuous shaking. Extracts were filter sterilized, freeze-dried and, chemically analyzed for saponin, flavonol, phenolic and tannin content. Chemical constituents of each extract were also identified by GC-MS analysis. The Minimum Inhibitory Concentration (MIC) of suitably diluted extracts of each plant part were also performed against C. neoformans and C. gattii, yeast pathogens commonly associated with HIV/AIDS sufferers.Results:Phytochemical analysis showed different concentrations of saponins (between 1023 and 2896.73 µg/ml), phenolics (between 16.48 and 51.58 µg/ml) and tannins (between 122.30 and 543.07 µg/ml) present in the different extracts. No flavonols were detected. GC-MS analysis identified a complex mixture of phytochemicals composed predominantly of sulphide, pyran, furan and ketone containing compounds to be present in the different plant parts. All extracts were dominated by the presence of 4 H-pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl, a pyran known to have antifungal properties. Although the root, leaf, rhizome and tuber extracts exhibited antifungal activities against both fungi, the rhizome and tuber extract were found to possess the lowest MIC’s of 1.25 mg/ml and 2.5 mg/ml against Cryptococcus neoformans and Cryptococcus gattii respectively.Conclusion:T. violacea extracts have a complex constituent of phytochemicals and each plant part exhibited a strong antifungal activity against C. neoformans and C. gattii. The rhizome and tuber extracts showed the highest antifungal activity against C. neoformans and C. gattii respectively. Thus, T. violacea aqueous extracts are strong candidates for further development into an antifungal chemotherapeutic agent.

The Antifungal Activity of Some Aliphatic and Aromatic Acids

1992 ◽  
Vol 57 (5) ◽  
pp. 1134-1142 ◽  
Author(s):  
Bohuslav Rittich ◽  
Marta Pirochtová ◽  
Jiří Hřib ◽  
Kamila Jurtíková ◽  
Petr Doležal
Keyword(s):  
Biological Activities ◽  
Pure Water ◽  
Water System ◽  
Penicillium Expansum ◽  
Aromatic Acids ◽  
Antifungal Activities ◽  
Aliphatic Acids ◽  
Significant Relationships ◽  
Physico Chemical ◽  
Connectivity Indices

The present paper deals with the relationship between biological activities of some aliphatic and aromatic acids and their physico-chemical parameters expressing the influence of hydrophobic factors. The test strain in the biotest of growth inhibition was the fungus Fusarium moniliforme CCMF-180 and Penicillium expansum CCMF-576. Significant relationship between antifungal activities of un-ionized form of aliphatic acids and their capacity factors (log k'0) extrapolated to pure water, partition coefficients determined in 1-octanol-water system (log Poct) and the first order of molecular connectivity indices (1χ) were calculated. The ionized form of aliphatic acids were antifungally active too. For benzoic acids significant relationships between antifungal activities and capacity factors of anionic form (log k'ia) were calculated.

Functional design of glycan-conjugated molecules using a chemoenzymatic approach

2021 ◽  
Author(s):  
Makoto Ogata
Keyword(s):  
Molecular Weight ◽  
Large Scale ◽  
Biological Activities ◽  
Natural Compounds ◽  
Low Molecular Weight ◽  
Functional Design ◽  
Enzymatic Method ◽  
Conjugated Molecules ◽  
Design Synthesis ◽  
And Function

Abstract Carbohydrates play important and diverse roles in the fundamental processes of life. We have established a method for accurately and a large scale synthesis of functional carbohydrates with diverse properties using a unique enzymatic method. Furthermore, various artificial glycan-conjugated molecules have been developed by adding these synthetic carbohydrates to macromolecules and to middle and low molecular weight molecules with different properties. These glycan-conjugated molecules have biological activities comparable to or higher than those of natural compounds, and present unique functions. In this review, several synthetic glycan-conjugated molecules are taken as examples to show design, synthesis and function.

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