scholarly journals Synthesis and evaluation of α-glucosidase and tyrosinase inhibitory activities of ester derivatives of usnic acid

2020 ◽  
Vol 23 (3) ◽  
pp. First
Author(s):  
Pham Duc Dung ◽  
Duong Thuc Huy ◽  
Nguyen Van Kieu
Keyword(s):  
Room Temperature ◽  
Acetyl Chloride ◽  
Usnic Acid ◽  
Anticancer Activities ◽  
Solubility In Water ◽  
Benzoyl Group ◽  
Inhibitory Activities ◽  
New Compounds ◽  
Derivatives Of ◽  
Low Solubility

Introduction: Usnic acid isolated from lichen was a potential bioactivity compound. It has a broad spectrum bioactivity, including antiviral, anti-inflammatory, anticancer… However, low solubility in water limited its application. Many researchs have done to overcome the restriction. Recent results showed that usnic acid derivatives bearing triazole, enamine, pyrazole and benzylidene groups had strong antiviral and anticancer activities. Thus, investigation of usnic acid derivatives synthesis was an attractive aspect due to the diversity of bioactivities of usnic acid derivatives. Methods: Usnic acid was isolated from lichen, six ester derivatives of usnic acid were synthesized from usnic acid with acetyl chloride and benzoyl chloride under stirring at room temperature. The products were evaluated α-glucosidase and tyrosinase inhibitory activities. Results: All the ester derivatives were created with good yields. All derivatives exhibited the same or higher activity comparing with usnic acid. Ester of usnic acid bearing benzoyl group showed excellent α-glucosidase activity with IC50 26.7±0.57 and 68.8±0.15 µM. Conclusion: Among the ester derivatives, UE1 and UE6 were reported as as new compounds. Interestingly, all products displayed the same or higher biological activity than the starting material, usnic acid when evaluated against α-glucosidase and tyrosinase.

Anti-Inflammatory 18β-Glycyrrhetinin Acid Derivatives Produced by Biocatalysis

Planta Medica ◽  
2018 ◽  
Vol 85 (01) ◽  
pp. 56-61 ◽  
Author(s):  
Boyi Fan ◽  
Baocheng Jiang ◽  
Sensen Yan ◽  
Bohui Xu ◽  
Huilian Huang ◽  
...  
Keyword(s):  
Glycyrrhetinic Acid ◽  
Mass Spectrometry Data ◽  
Ionization Mass ◽  
Mild Conditions ◽  
Data Analyses ◽  
Inhibitory Activities ◽  
Anti Inflammatory ◽  
Specific Reactions ◽  
New Compounds ◽  
Derivatives Of

AbstractIn this study, the biocatalysis of 18β-glycyrrhetinic acid by two strains of filamentous fungi, namely Rhizopus arrhizus AS 3.2893 and Circinella muscae AS 3.2695, was investigated. Scaled-up biotransformation reactions yielded 14 metabolites. Their structures were established based on extensive nuclear magnetic resonance and high-resolution electrospray ionization mass spectrometry data analyses, and seven of them are new compounds. The two fungal strains exhibited distinct biocatalytic features. R. arrhizus could catalyze hydroxylation and carbonylation reactions, whereas C. muscae preferred to catalyze hydroxylation and glycosidation reactions. These highly specific reactions are difficult to achieve by chemical synthesis, particularly under mild conditions. Furthermore, we found that most of the metabolites exhibited pronounced inhibitory activities on lipopolysaccharides-induced nitric oxide production in RAW264.7 cells. These biotransformed derivatives of 18β-glycyrrhetinic acid could be potential anti-inflammatory agents.

scholarly journals Synthesis of morpholinium salts based on chloroacylated derivatives of dihydroquercetin

2019 ◽  
Vol 59 (7) ◽  
pp. 37-42
Author(s):  
Anton O. Pozdeev ◽  
◽  
Alexander M. Koroteev ◽  
Sofia N. Pimankina ◽  
Mikhail P. Koroteev ◽  
...  
Keyword(s):  
Water Solubility ◽  
Biological Activities ◽  
High Water ◽  
Water Soluble ◽  
Synthetic Approach ◽  
Solubility In Water ◽  
Natural Amino Acids ◽  
Synthetic Approaches ◽  
Derivatives Of ◽  
Low Solubility

The flavonoid dihydroquercetin and its esterified derivatives possess various biological activities and are widely used as dietary supplements and in pharmacology. A significant disadvantage of this flavonoid is its low solubility in water at ordinary temperatures of up to 0.03%, which negatively affects its biological activity. Nature overcomes this problem by glycosylation, sulfation, and phosphorylation. In chemistry and pharmacology to overcome this problem, there are several synthetic approaches. For dihydroquercetin (DHQ) is the inclusion of DHQ in the cyclodextrin matrix or the formation of a complex of DHQ with basic natural amino acids. In this paper, a method is proposed for obtaining water-soluble morpholinium salts based on chloroacylated derivatives of DHQ. The acylation reaction was carried out in dioxane, pyridine was used as an acceptor of choric hydrogen. The target compounds were obtained with a yield of 68-79%. As a result, chlorinated derivatives based on DHQ and its acyl and benzyl derivatives were synthesized. These derivatives in the interaction with morpholine form its salts, which, as it turned out, have a high water solubility. Pentamorpholine salt of DHQ had the highest solubility in water, up to 6.5% at room temperature, which is 200 times more soluble than the original DHQ. The proposed synthetic approach to increase the water solubility of acyl derivatives of DHQ can be extended using other nitrogenous bases and other haloacyl derivatives of DHQ.

scholarly journals Condensation Reactions of Methyl Derivatives of Quinoxaline-1,4-Dioxide with 4,4'-Biphenyl Carboxaldehyde

2021 ◽  
pp. 15-21
Author(s):  
Mohamad Alkhudari
Keyword(s):  
Room Temperature ◽  
Condensation Reaction ◽  
Absolute Methanol ◽  
Spectroscopic Techniques ◽  
Condensation Reactions ◽  
Limited Success ◽  
Methyl Derivatives ◽  
New Compounds ◽  
Derivatives Of

Aims: To synthesis new compounds via condensation reactions between 2-methyl quinoxaline-1,4-dioxide derivatives 4,4'-biphenyl carboxaldehyde. Methodology: The Quinoxalines derivatives were prepared from 2-nitroaniline derivatives using the Beirut reaction, and the condensation reaction was carried out at room temperature in absolute methanol. Based on IR and NMR spectroscopic techniques, the structures of all products have been suggested. For their synthesis, suitable mechanisms have been suggested. Results: In this work, condensation reactions involving 2-methyl quinoxaline-1,4-dioxide derivatives and 4,4'-biphenyl carboxaldehyde were performed. Conclusion: The final compounds, we suppose, have considerable applications in fluorescent and chromophoric activities. In all known solvents, the products were just slightly soluble. Products have been subjected to sulfonation reactions, although with limited success.

scholarly journals Preparation and Properties of (1-Hydroxyethylidene) Diphosphonic Acid Aminium Salts

2021 ◽  
Vol 13 (1) ◽  
pp. 88-96
Author(s):  
V.V. Semenov ◽  
Keyword(s):  
Organic Media ◽  
Aminobenzoic Acid ◽  
Diphosphonic Acid ◽  
Solid Complex ◽  
Preparation Methods ◽  
Solubility In Water ◽  
Good Solubility ◽  
Oligomeric Form ◽  
Derivatives Of ◽  
Low Solubility

An overview of the preparation methods and properties of (1-hydroxyethylidene) diphosphonic acid aminium salts is presented. (1-Hydroxyethylidene) diphosphonic acid with monoethanolamine forms a crystalline compound, which, according to the elemental analysis and XRD data, is ternary C(CH3)(OH)[P(O)O-NH3+CH2CH2OH]3[P(O)(OH)] amine salt. A characteristic feature of the derivatives of (1-hydroxyethylidene) diphosphonic acid and tris (hydroxymethyl)aminomethane is the formation of glassy and resinous products. Their composition Н4L∙4NH2C(CH2OH)3 corresponds to 4 base molecules per 1 tetrabasic acid molecule. The addition of 4 molecules of the primary amine occurs both when the ratio of the initial reagents is 1: 4 and 1: 3. The polymer structure and the presence of strong hydrogen bonds in the Н4L∙4NH2C(CH2OH)3 compound lead to its very low solubility in organic media and good solubility in water. The solubility of Н4L∙4NH2C(CH2OH)3 in methanol is 1.8 g per 100 mL. The reaction of (1-hydroxyethylidene)diphosphonic acid with para-aminobenzoic acid leads to the formation of bis(4-carboxyphenylamine)(1-hydroxyethylidene)diphosphonate C(CH3)(OH)[P(O)(OH)O-NH3+C6H4С(О)ОН]2. In a crystal, this compound consists of the anion of the double-deprotonated (1-hydroxyethylidene)diphosphonic acid C(CH3)(OH)[P(OH)(O)O-]2 and two amine cations NH3+C6H4С(О)ОН. The tetrabasic acid binds 3 molecules of morpholine, giving tris(morpholinium)(1-hydroxyethylidene)diphosphonate H4L•3HN(CH2CH2)2O in the form of a white powder that dissolves well in water, methyl and ethyl alcohols. The solid complex of morpholine with (1-hydroxyethylidene)diphosphonic acid does not crystallize from various solvents, which may be caused by the oligomeric form of morpholine included in the molecule of the complex with H4L.

SOME DIRECTIONS IN THE MODIFICATION OF AZOLES

2020 ◽  
Vol 5 (443) ◽  
pp. 85-91
Author(s):  
Ibrayev M.K., ◽  
◽  
Takibayeva A.T., ◽  
Fazylov S.D., ◽  
Rakhimberlinova Zh.B., ◽  
...  
Keyword(s):  
13C Nmr Spectroscopy ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Synthesis Conditions ◽  
Alkaloid Cytisine ◽  
Azole Ring ◽  
Cyclic Compounds ◽  
New Compounds ◽  
Derivatives Of

This article presents studies on the targeted search for new derivatives of azoles, such as benzthiazole, 3,5-dimethylpyrazole, 1,3,4-oxadiazole-2-thione, 1,3,4-thiadiazole. The possibility of combining in one molecule of the azole ring with other cyclic compounds: the alkaloid cytisine, morpholine, furan and some arenes has been studied. To obtain new compounds, the reactions of bromination, acylation, and interaction with isothiocyanates were studied. Optimal synthesis conditions were studied for all reactions. It was found that the reaction of 4-bromo-3,5-dimethylpyrazole with isothiocyanates, in contrast to the previously written derivatives of anilines, takes a longer time and requires heating the reaction mixture. The combination of a pirasol fragment with halide substituents often results in an enhanced therapeutic effect. The synthesized 2-bromine-N-(6-rodanbenzo[d]thiazole-2-yl)acetamide, due to the alkylbromide group, is an important synth in the synthesis of new benzthiazole derivatives. Its derivatives combine in one molecule the rest of rhodanbenzthiazole with alkaloid cytisine and biogenic amine morpholine and are potentially biologically active compounds, since the molecule structure contains several pharmacophoric fragments: benzthiazole and alkaloid (amine) heterocycles, rhodane and urea groups. The mechanism of formation of 1,3,4-oxadiazole-2-tyons from hydrazides under action on them by carbon disulfide was studied and assumed. It was shown that dithiocarbamates in acidic medium decompose with the release of hydrogen sulfide and the formation of highly reactive isothiocyanate group. Then, intra-molecular cyclization occurs, with the formation of end products - 1,3,4-oxadiazole-2-thions. The structures of the synthesized compounds were studied by 1H and 13C NMR spectroscopy. All synthesized substances are potentially biologically active compounds, since they contain several pharmacophore fragments in their structure.

Synthesis and Antimicrobial activities of Some Polyphenol compounds by Nano ZnO-TBAB as a Heterogeneous Catalytic Media

2020 ◽  
Vol 17 ◽  
Author(s):  
Rahele Bargebid ◽  
Ali Khalafi-Nezhad ◽  
Kamiar Zomorodian ◽  
Leila Zamani ◽  
Ali Ahmadinejad ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Antimicrobial Activities ◽  
Reusable Catalyst ◽  
Nano Zno ◽  
Antifungal Activities ◽  
Chemical Structures ◽  
Heterogeneous Catalytic ◽  
Solvent Free Conditions ◽  
New Compounds ◽  
Derivatives Of

Introduction: Mannich reaction is a typical example of a three-component condensation reaction and the chemistry of Mannich bases has been the matter of search by researchers. Here an efficient procedure for the synthesis of some new Mannich derivatives of simple phenols is described. Methods: In this procedure a microwave-assisted and solvent less condensation were done between different phenols, secondary amines and paraformaldehyde. The reactions proceed in the presence of catalytic amount of nano ZnO and tetrabutylammonium bromide (TBAB) in excellent yields. 10 new compounds were synthesized (A1-A10). Chemical structures of all new compounds were confirmed by different spectroscopic methods. We optimized the chemical reactions in different conditions. Optimization reactions were done in the presence of different mineral oxides, different amount of TBAB and also different solvents. Nano ZnO and TBAB in catalytic amounts and solvent free conditions were the best conditions. All the synthesized compounds were screened for their antimicrobial activities. Antifungal and antibacterial activities of the synthesized compounds were evaluated against some Candida, filaments fungi, gram positive and gram negative bacteria by broth micro dilution method as recommended by CLSI. Results: The result showed that compounds A2, A3 and A4 against most of the tested Candida species and compounds A5 and A7 against C. parapsilosis and C. tropicalis, exhibited considerable antifungal activities. Also Compounds A8 and A10 showed desirable antifungal activities against C. neoformance and C. parapsilosis, respectively. The antibacterial activities of the synthesized compounds were also evaluated. Compounds A6 - A10 against E. Fecalis and compounds A5, A7, A9 and A10 against P. aeruginosa showed desirable antibacterial activities. Discussion: We have synthesized some new Mannich adducts of poly-hydroxyl phenols in the presence of nano-ZnO as a reusable catalyst, with the hope of discovering new lead compounds serving as potent antimicrobial agents. The advantages of this method are generality, high yields with short reaction times, simplicity, low cost and matching with green chemistry protocols. The antimicriobial studies of Mannich derivatives of phenols showed desirable results in vitro.

Development of the room temperature protocol based on room temperature ionic liquids and surfactant ionic liquids for the synthesis of derivatives of 2-amino-thiazoles and thermo-physical analysis of the synthesized derivatives using TGA-DSC.

2020 ◽  
Vol 10 ◽  
Author(s):  
Chandrakant Sarode ◽  
Sachin Yeole ◽  
Ganesh Chaudhari ◽  
Govinda Waghulde ◽  
Gaurav Gupta
Keyword(s):  
Thermal Analysis ◽  
Heat Capacity ◽  
Ionic Liquids ◽  
Specific Heat ◽  
Specific Heat Capacity ◽  
Room Temperature ◽  
Heat Capacity Data ◽  
General Strategy ◽  
Capacity Data ◽  
Derivatives Of

Aims: To develop an efficient protocol, which involves an elegant exploration of the catalytic potential of both the room temperature and surfactant ionic liquids towards the synthesis of biologically important derivatives of 2-aminothiazole. Objective: Specific heat capacity data as a function of temperature for the synthesized 2- aminothiazole derivatives has been advanced by exploring their thermal profiles. Method: The thermal gravimetry analysis and differential scanning calorimetry techniques are used systematically. Results: The present strategy could prove to be a useful general strategy for researchers working in the field of surfactants and surfactant based ionic liquids towards their exploration in organic synthesis. In addition to that, effect of electronic parameters on the melting temperature of the corresponding 2-aminothiazole has been demonstrated with the help of thermal analysis. Specific heat capacity data as a function of temperature for the synthesized 2-aminothiazole derivatives has also been reported. Conclusion: Melting behavior of the synthesized 2-aminothiazole derivatives is to be described on the basis of electronic effects with the help of thermal analysis. Additionally, the specific heat capacity data can be helpful to the chemists, those are engaged in chemical modelling as well as docking studies. Furthermore, the data also helps to determine valuable thermodynamic parameters such as entropy and enthalpy.

scholarly journals Novel Derivatives of 4-Methyl-1,2,3-Thiadiazole-5-Carboxylic Acid Hydrazide: Synthesis, Lipophilicity, and In Vitro Antimicrobial Activity Screening

2021 ◽  
Vol 11 (3) ◽  
pp. 1180
Author(s):  
Kinga Paruch ◽  
Łukasz Popiołek ◽  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Malm ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Carboxylic Acid ◽  
Bacterial Infections ◽  
Acid Hydrazide ◽  
Antimicrobial Effect ◽  
In Vitro Antimicrobial Activity ◽  
Research Goal ◽  
New Compounds ◽  
Derivatives Of

Bacterial infections, especially those caused by strains resistant to commonly used antibiotics and chemotherapeutics, are still a current threat to public health. Therefore, the search for new molecules with potential antimicrobial activity is an important research goal. In this article, we present the synthesis and evaluation of the in vitro antimicrobial activity of a series of 15 new derivatives of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. The potential antimicrobial effect of the new compounds was observed mainly against Gram-positive bacteria. Compound 15, with the 5-nitro-2-furoyl moiety, showed the highest bioactivity: minimum inhibitory concentration (MIC) = 1.95–15.62 µg/mL and minimum bactericidal concentration (MBC)/MIC = 1–4 µg/mL.

scholarly journals New Diterpenoids and Isocoumarin Derivatives from the Mangrove-Derived Fungus Hypoxylon sp.

Marine Drugs ◽  
2021 ◽  
Vol 19 (7) ◽  
pp. 362
Author(s):  
Bolin Hou ◽  
Sushi Liu ◽  
Ruiyun Huo ◽  
Yueqian Li ◽  
Jinwei Ren ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Crude Extract ◽  
Mass Spectrometric ◽  
Spectrometric Analysis ◽  
Ic50 Values ◽  
Inhibitory Activities ◽  
The Absolute ◽  
Dpph Scavenging ◽  
New Compounds

Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (4–7), together, with seven known metabolites (3 and 8–13) were obtained from the crude extract of the mangrove-derived fungus Hypoxylon sp. The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of compounds 1, 2, 4, 5, and 7 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, and the absolute configurations of C-4′ in 6 and C-9 in 7 were determined by [Rh2(OCOCF3)4]-induced ECD spectra. Compound 1 showed moderate α-glucosidase inhibitory activities with IC50 values of 741.5 ± 2.83 μM. Compounds 6 and 11 exhibited DPPH scavenging activities with IC50 values of 15.36 ± 0.24 and 3.69 ± 0.07 μM, respectively.

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