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Microwave-assisted green synthesis of bile acid derivatives and evaluation of glucocorticoid receptor binding.

ABSTRACT: Herein, we present microwave-assisted AlCl₃ catalyzed oxidation of bile acid hydroxyl groups in the presence of Oxone® in water media. Significant rate enhancements were observed for Wolff-Kishner reduction of synthesized bile acids oxo derivatives to the 5β-cholanic acid. Reaction of amidation of the simplest bile acid and aminolysis of the deoxycholic acid was accomplished in the absence of solvent and catalysts under sealed vessel microwave conditions. Because 5β-cholanic acid reportedly modulates glucocorticoid receptor signaling in cell models of Parkinson's disease, we tested the affinity of 5β-cholanic acid and deoxycholic acid derivatives for the glucocorticoid receptor in vitro using a yeast-based fluorescent screen. Treatment of GR-expressing yeast with prednisolone resulted in a dose-dependent increase in fluorescence; whereas 5β-cholanic acid binds to the glucocorticoid receptor with more moderate affinity. Similarly, molecular docking also suggests that 5β-cholanic acid can bind to the glucocorticoid receptor, with similar geometry to known GR ligands.

SUBMITTER: Vasiljevic BR

PROVIDER: S-EPMC8128055 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Microwave assisted one-pot green synthesis of cinnoline derivatives inside natural sporopollenin microcapsules.

Project description:We present a green and efficient approach for the synthesis of novel cinnoline derivatives inside natural Lycopodium clavatum sporopollenin (LCS) microcapsules via a one-pot microwave (MW) assisted reaction for the first time. We also propose the concept that the robust micrometre-sized sporopollenin microcapsules can act as MW microreactors. We demonstrate the feasibility of this concept by in situ synthesising 8-hydroxy-7-nitro-6-(3-nitrophenyl)-3-oxo-2-(p-tolyl)-2,3,5,6-tetrahydrocinnoline-4-carbonitrile inside the LCS microcapsules via a microwave (MW) assisted reaction of ethyl 5-cyano-4-methyl-6-oxo-1-(p-tolyl)-1,6-dihydropyridazine-3-carboxylate with 1-nitro-2-phenylethylene in the presence of piperidine as a base at 100 °C for 20 minutes. The LCS microparticles are extensively characterised before and after the MW induced reaction using several techniques. The formation of the cinnoline compound inside the LCS microcapsules is confirmed by laser scanning confocal microscopy (LSCM), X-ray diffraction (XRD) and fourier-transform infrared spectroscopy (FTIR) analyses. Using liquid chromatography-mass spectrometry (LCMS) analyses, we show that the structural integrity of the cinnoline compound, recovered from the cinnoline loaded (cinn-loaded) LCS, is preserved. The pure cinnoline is found to show promising optical properties with two λ max absorption peaks at 310 and 610 nm. Both the pure cinnoline and cinn-loaded LCS show promising antibacterial activity against Pseudomonas aeruginosa (Gram-negative) and Bacillus cereus (Gram-negative) human pathogenic bacterial strains. The successful MW induced reaction of the prominent cinnoline derivative inside the biocompatible LCS microreactors can open up intriguing applications in materials and pharmaceutical sciences.

| S-EPMC9081757 | biostudies-literature

Microwave-assisted synthesis of rhodamine derivatives.

Project description:The microwave synthesis of 12 rhodamine-derived imines is described. The present work involves condensation of rhodamine hydrazide with various aromatic aldehydes in ethanol under microwave irradiation. The results obtained indicate that, unlike classical heating, microwave irradiation results in higher yields, shorter reaction time, mild reaction condition and simple work-up procedure. The structures of synthesized compounds were confirmed by 1H-NMR, 13C-NMR, FT-IR and high-resolution mass spectra data.

| S-EPMC7082095 | biostudies-literature

Microwave-assisted synthesis and antitumor evaluation of a new series of thiazolylcoumarin derivatives.

Project description:A new series of thiazolylcoumarin derivatives was synthesized. The designed strategy embraced a molecular hybridization approach which involves the combination of the thiazole and coumarin pharmacophores together. The new hybrid compounds were tested for in vitro antitumor efficacy over cervical (Hela) and kidney fibroblast (COS-7) cancer cells. Compounds 5f, 5h, 5m and 5r displayed promising efficacy toward Hela cell line. In addition, 5h and 5r were found to be the most active candidates toward COS-7 cell line. The four active analogs, 5f, 5h, 5m and 5r were screened for in vivo antitumor activity over EAC cells in mice, as well as in vitro cytotoxicity toward W138 normal cells. Results illustrated that 5r has the highest in vivo activity, and that the four analogs are less cytotoxic than 5-FU toward W138 normal cells. In this study, 3D pharmacophore analysis was performed to investigate the matching pharmacophoric features of the synthesized compounds with trichostatin A. In silico studies showed that the investigated compounds meet the optimal needs for good oral absorption with no expected toxicity hazards.

| S-EPMC5735336 | biostudies-literature

The Microwave-Assisted Green Synthesis of TiC Powders.

Project description:Titanium carbide (TiC) is an important engineering material and has found widespread applications. Currently, TiC is typically synthesized through carbothermal reduction, requiring a high temperature (ca. 1700-2300 °C) and long reaction time (ca. 10-20 h), which is not eco-friendly. During a conventional reaction path, anatase TiO₂ (A-TiO₂) was first converted to rutile TiO₂ (R-TiO₂), which was subsequently reduced to TiC. Herein, we explored the synthesis of TiC powders with the assistance of microwave heating. In particular, we achieved the conversion of A-TiO₂, which was more reactive than R-TiO₂ for the carbothermal reduction, to TiC, which was directly due to quick microwave heating. As such, the carbothermal reduction started at a much lower temperature of ca. 1200 °C and finished within 30 min when reacting at 1400 °C, leading to significant energy saving. This study shows that microwave-assisted synthesis can be an effective and green process for preparing TiC powders, which is promising for future large-scale production. The influence of the reaction temperature, the reaction duration, and the carbon content on the synthesis of TiC powders was investigated.

| S-EPMC5457278 | biostudies-other

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Project description:Microwave-assisted synthesis of near-infrared fluorescent sphingosine derivatives is described, and the utility of the probes demonstrated by co-localization studies with visible wavelength fluorescent sphingosine derivatives.

| S-EPMC2696400 | biostudies-literature

Microwave-Assisted Synthesis of Aminophosphonic Derivatives and Their Antifungal Evaluation against <i>Lomentospora prolificans</i>.

Project description:Lomentospora prolificans is a pathogenic and multidrug-resistant fungus that can infect both immunocompetent and immunocompromised patients, with mortality rates up to 87%. The World Health Organization (WHO) included this fungal species in its first list of 19 priority fungal pathogens, which focused on fungal pathogens that can cause invasive acute and subacute systemic fungal infections. Therefore, there is a growing interest in finding new therapeutic alternatives. In this work, the synthesis of twelve α-aminophosphonates by the microwave-assisted Kabachnik-Fields reaction and twelve α-aminophosphonic acids by a monohydrolysis reaction is reported. All compounds were evaluated by the agar diffusion method as a preliminary screening in comparison with voriconazole, showing inhibition halos for compounds 7, 11, 13, 22 and 27. The five active compounds in the preliminary tests were evaluated against five strains of L. prolificans following protocol M38-A2 from CLSI. The results showed that these compounds exhibit antifungal activity in the concentration range of 900->900 μg/mL. Cytotoxicity against healthy COS-7 cells was also evaluated by the MTT assay, and it was shown that compound 22 was the least cytotoxic, with a viability of 67.91%, comparable to the viability exhibited by voriconazole (68.55%). Docking studies showed that the possible mechanism of action of the active compounds could be through the inhibition of the enzyme lanosterol-14-alpha-demethylase in an allosteric hydrophobic cavity.

| S-EPMC10224343 | biostudies-literature

Microwave-Assisted Synthesis of Trazodone and Its Derivatives as New 5-HT1A Ligands: Binding and Docking Studies.

Project description:Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its derivatives. In the known methods of the synthesis of trazodone and its derivatives, organic and toxic solvents are used, and the synthesis time varies from several to several dozen hours. Our research shows that trazodone and its derivatives can be successfully obtained in the presence of potassium carbonate as a reaction medium in the microwave field in a few minutes. As a result of the research work, 17 derivatives of trazodone were obtained, including compounds that exhibit the characteristics of 5-HT1A receptor ligands. Molecular modeling studies were performed to understand the differences in the activity toward 5-HT1A and 5-HT2A receptors between ligand 10a (2-(6-(4-(3-chlorophenyl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one) (5-HT1AKi = 16 nM) and trazodone. The docking results indicate the lack of the binding of ligand 10a to 5-HT2AR, which is consistent with the in vitro studies. On the other hand, the docking results for the 5-HT1A receptor indicate two possible binding modes. Crystallographic studies support the hypothesis of an extended conformation.

| S-EPMC6515286 | biostudies-literature

Design and Microwave Assisted Synthesis of Coumarin Derivatives as PDE Inhibitors.

Project description:Coumarins appended to benzimidazole through pyrazole are designed and synthesized using microwave irradiation. These compounds were analyzed for phosphodiesterase (PDE) inhibition indirectly by motility pattern in human spermatozoa. Some of the synthesized compounds, namely, 5d, 5e, 5f, 5g, 5h, and 5k, have exhibited potent inhibitory activity on PDE.

| S-EPMC4779523 | biostudies-literature

Microwave-Assisted Synthesis and Spectral Properties of Pyrrolidine-Fused Chlorin Derivatives.

Project description:In this work we pursued research involving the microwave-assisted N-alkylation of a NH pyrrolidine-fused chlorin with methyl 4-(bromomethyl) benzoate and subsequent ester hydrolysis as a straightforward strategy to obtain carboxylic acid functionality in the pyrrolidine-fused chlorin, as a single reaction product. We studied the reaction's scope by extending the N-alkylation of the free-base chlorin and its corresponding Zn(II) complex to other alkyl halides, including 1,4-diiodobutane, N-(2-bromoethyl)phthalimide, and 2-bromoethanaminium bromide. In addition, two new chlorin-dansyl dyads were synthesized by reacting dansyl chloride with the 2-aminoethyl pyrrolidine-fused chlorin (dyad 6) and NH pyrrolidine-fused chlorin (dyad 7). According to spectral studies, the linker length between the two fluorophores influences the response of the dyads to the solvent polarity. Because of the simplicity of these approaches, we believe it will enable access to a vast library of custom-tailored N-functionalized chlorins while preserving their important absorption and emission spectra as photosensitizers in photodynamic therapy (PDT) of cancer and photodynamic inactivation (PDI) of microorganisms.

| S-EPMC10179977 | biostudies-literature

Microwave-assisted efficient and facile synthesis of tetramic acid derivatives via a one-pot post-Ugi cascade reaction.

Project description:A facile microwave-assisted method for the synthesis of tetramic acid derivatives has been developed through an Ugi/Dieckmann cyclization strategy with DBU. This two-step one-pot procedure afforded the targeted tetramic acid analogues in good yields. With commercially available Ugi starting materials, microwave irradiation, a simple operation, excellent yields, and a broad scope, this reaction has the potential to produce a large number of tetramic acid analogues, which cannot be easily accessed by the classic synthetic methods.

| S-EPMC7155898 | biostudies-literature

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