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.

Synthesis and anti-HIV Activity of New Benzimidazole, Benzothiazole and Carbohyrazide Derivatives of the anti-Inflammatory Drug Indomethacin

2011 ◽  
Vol 66 (9) ◽  
pp. 953-960 ◽  
Author(s):  
Najim A. Al-Masoudi ◽  
Nadhir N. A. Jafar ◽  
Layla J. Abbas ◽  
Sadiq J. Baqir ◽  
Christophe Pannecouque
Keyword(s):  
Phenyl Isothiocyanate ◽  
Reverse Transcriptase Inhibitors ◽  
Inflammatory Drug ◽  
Oxadiazole Derivatives ◽  
Anti Inflammatory ◽  
New Compounds ◽  
Further Development ◽  
Derivatives Of ◽  
Anti Hiv ◽  
Hiv 1

There is an urgent need for the design and development of new and safer drugs for the treatment of HIV infection, active against the currently resistant viral strains. New derivatives of the non-steroidal anti-inflammatory drug indomethacin bearing benzimidazoles, benzothiazole, purine and pyridine residues 8 - 13 were synthesized with the aim of developing new non-nucleoside reverse transcriptase inhibitors (NNRTIs).Alternatively, new imine analogs 16 - 20 were synthesized from condensation of indomethacinyl hydrazide 15, prepared from the ester 14, with various ketone precursors. Treatment of 15 with phenyl isothiocyanate or triethyl orthoformate afforded the phenylcarbonothioyl and the oxadiazole derivatives 21 and 22, respectively. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. Compounds 9 and 10 were the most active in inhibiting HIV-2 and HIV-1, respectively, with EC50 ≥ 17.60 μgmL−1 and > 1.15 μgmL−1 (therapeutic indexes (SI) of ≥ 3 and < 1, respectively), and are leading candidates for further development.

scholarly journals Thiazolidin-4-one, azetidin-2-one and 1,3,4-oxadiazole derivatives of isonicotinic acid hydrazide: Synthesis and their biological evaluation

2011 ◽  
Vol 76 (8) ◽  
pp. 1057-1067 ◽  
Author(s):  
Sadaf Gilani ◽  
Suroor Khan ◽  
Ozair Alam ◽  
Vijender Singh ◽  
Alka Arora
Keyword(s):  
Lipid Peroxidation ◽  
Acid Hydrazide ◽  
Inflammatory Activity ◽  
Paw Edema ◽  
Rat Paw Edema ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
New Compounds ◽  
Derivatives Of ◽  
Ulcerogenic Action

A series of thiazolidin-4-one (2a-h, 3a-h), azetidin-2-one (4a- h) and 1,3,4-oxadiazole (5a-h) derivatives of isoninicotinic acid hydrazide (INH) were synthesized in order to obtain new compounds with potential anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities. The structures of the new compounds were supported by their IR, 1H-NMR and mass spectral data. All compounds were evaluated for their anti-inflammatory activity by the carrageenan-induced rat paw edema test method. Eleven of the new compounds, out of 32, showed very good anti-inflammatory activity in the carrageenan-induced rat paw edema test, with significant analgesic activity in the tail immersion method together with negligible ulcerogenic action. The compounds, which showed less ulcerogenic action, also showed reduced malondialdehyde content (MDA), which is one of the by-products of lipid peroxidation. The study showed that the compounds inhibited the induction of gastric mucosal lesions and it can be suggested from the results that their protective effects may be related to inhibition of lipid peroxidation in the gastric mucosa.

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.

Cationic β-vinyl substitutedmeso-tetraphenylporphyrins: synthesis and non-covalent interactions with a short poly(dGdC) duplex

2012 ◽  
Vol 16 (01) ◽  
pp. 101-113 ◽  
Author(s):  
Eduarda M.P. Silva ◽  
Catarina I.V. Ramos ◽  
Patrícia M.R. Pereira ◽  
Francesca Giuntini ◽  
Maria A.F. Faustino ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Binding Mode ◽  
Ionization Mass ◽  
Alkyl Derivatives ◽  
Vis Spectroscopy ◽  
One Step ◽  
Probable Occurrence ◽  
Non Covalent Interactions ◽  
New Compounds ◽  
Derivatives Of

Several cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso-tetraphenylporphyrin derivatives were synthesized starting from 2-formyl-meso-tetraphenylporphyrin, and the corresponding Zn(II) complex, and different N-alkyl derivatives of 2- and 4-methylpyridine and 2- and 4-methylquinoline. The new compounds were obtained in a one-step process via base catalyzed aldol-type condensation reactions. Electrospray ionization mass spectrometry (ESI-MS) and ultraviolet-visible (UV-vis) spectroscopy were used to investigate the binding mode of the synthesized cationic beta-vinyl-pyridinium and beta-vinyl-quinolinium-meso-tetraphenylporphyrin derivatives with a short GC duplex oligonucleotide. Analysis of the obtained mass spectrometry results indicates the probable occurrence of outside binding. UV-vis spectroscopy data also points to non-intercalation. The potential photosensitizing capacity of these compounds was also ascertained from preliminary photophysical studies.

Funktionelle Trimethylphosphanderivate, XVII [1] Methyl-bis(dimethylphosphinomethyl)phosphan, (Me2PCH2)2PMe / Functional Derivatives of Trimethylphosphane, XVII [1] Methyl-bis(dimethylphosphinomethyl)phosphane, (Me2PCH2)2PMe

1982 ◽  
Vol 37 (3) ◽  
pp. 284-291 ◽  
Author(s):  
Hans H. Karsch
Keyword(s):  
Pure State ◽  
Mild Conditions ◽  
Nmr Data ◽  
Functional Derivatives ◽  
New Compounds ◽  
Hydrolysis Of ◽  
Derivatives Of ◽  
Membered Heterocycle

(Me2PCH2)2PMe (3) is obtained from MePCl2 (2a) or MeP(OPh)2 (2b) and LiCH2PMe2 (1). The oxides [Me2P(O)CH2]2PMe (4) and [Me2P(O)CH2]2P(O)Me (5), are formed on the reaction with air. Quaternisation with Mel gives the salts [(Me3PCH2)2PMe]I2 (6) and [(Me3PCH2)2PMe2]I3 (12). For comparison, also the isoelectronic (Me3SiCH2)2PMe (7), and (Me3SiCH2)2PtBu (8), are synthesized and transformed to their methylphosphonium salts 10 and 11. With CH2Br2, 3 forms the six-membered heterocycle [MeP(CH2PMe2)2CH2]Br2 (13a), which could not be isolated in a pure state, however. 3 may be metalated by LiBu: Li[Me2PCHP(Me)CH2PMe2] (15), is obtained, but a second metalation step could not be observed. The hydrolysis of 12 under unusual mild conditions (H2O or H2O/CH3OH) gives [Me2P(O)CH2PMe3]I (16), and [Me4P]I (17), as main products. Properties and NMR data of the new compounds are described.

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.

scholarly journals Structural Characterization and Assessment of Anti-Inflammatory and Anti-Tyrosinase Activities of Polyphenols from Melastoma normale

Molecules ◽  
2021 ◽  
Vol 26 (13) ◽  
pp. 3913
Author(s):  
Rui-Jie He ◽  
Jun Li ◽  
Yong-Lin Huang ◽  
Ya-Feng Wang ◽  
Bing-Yuan Yang ◽  
...  
Keyword(s):  
Enzyme Inhibitors ◽  
Enzyme Inhibitor ◽  
Structure Identification ◽  
No Production ◽  
Protective Effects ◽  
Successful Isolation ◽  
Ic50 Values ◽  
Development And Utilization ◽  
Inhibitory Activities ◽  
Anti Inflammatory

Polyphenols, widely distributed in the genus Melastoma plants, possess extensive cellular protective effects such as anti-inflammatory, anti-tyrosinase, and anti-obesity, which makes it a potential anti-inflammatory drug or enzyme inhibitor. Therefore, the aim of this study is to screen for the anti-inflammatory and enzyme inhibitory activities of compounds from title plant. Using silica gel, MCI, ODS C18, and Sephadex LH-20 column chromatography, as well as semipreparative HPLC, the extract of Melastoma normale roots was separated. Four new ellagitannins, Whiskey tannin C (1), 1-O-(4-methoxygalloyl)-6-O-galloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (2), 1-O-galloyl-6-O-(3-methoxygalloyl)-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (3), and 1-O-galloyl-6-O-vanilloyl-2,3-O-(S)-hexahydroxydiphenoyl-β-d-glucose (4), along with eight known polyphenols were firstly obtained from this plant. The structures of all isolates were elucidated by HRMS, NMR, and CD analyses. Using lipopolysaccharide (LPS)-stimulated RAW2 64.7 cells, we investigated the anti-inflammatory activities of compounds 1–4, unfortunately, none of them exhibit inhibit nitric oxide (NO) production, their IC50 values are all > 50 μM. Anti-tyrosinase activity assays was done by tyrosinase inhibition activity screening model. Compound 1 showed weak tyrosinase inhibitory activity with IC50 values of 426.02 ± 11.31 μM. Compounds 2–4 displayed moderate tyrosinase inhibitory activities with IC50 values in the range of 124.74 ± 3.12–241.41 ± 6.23 μM. The structure–activity relationships indicate that hydroxylation at C-3′, C-4′, and C-3 in the flavones were key to their anti-tyrosinase activities. The successful isolation and structure identification of ellagitannin provide materials for the screening of anti-inflammatory drugs and enzyme inhibitors, and also contribute to the development and utilization of M. normale.

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