ABSTRACT
ß-Ketophosphonates with pentalenofurane fragments linked to the keto group were synthesized. The bulky pentalenofurane skeleton is expected to introduce more hindrance in the prostaglandin analogues of type III, greater than that obtained with the bicyclo[3.3.0]oct(a)ene fragments of prostaglandin analogues I and II, to slow down (retard) the inactivation of the prostaglandin analogues by oxidation of 15α-OH to the 15-keto group via the 15-PGDH pathway. Their synthesis was performed by a sequence of three high yield reactions, starting from the pentalenofurane alcohols 2, oxidation of alcohols to acids 3, esterification of acids 3 to methyl esters 4 and reaction of the esters 4 with lithium salt of dimethyl methanephosphonate at low temperature. The secondary compounds 6b and 6c were formed in small amounts in the oxidation reactions of 2b and 2c, and the NMR spectroscopy showed that their structure is that of an ester of the acid with the starting alcohol. Their molecular structures were confirmed by single crystal X-ray determination method for 6c and XRPD powder method for 6b.
Subject(s)
Ketones/chemistry , Organophosphonates/chemistry , Prostaglandins, Synthetic/chemical synthesis , Chemistry Techniques, Synthetic , Crystallography, X-Ray , Models, Molecular , Molecular Conformation , Molecular Structure , Prostaglandins, Synthetic/chemistry , Sesquiterpenes/chemistryABSTRACT
New 1'-homocarbanucleoside analogs with an optically active substituted bicyclo[2.2.1]heptane skeleton as sugar moiety were synthesized. The pyrimidine analogs with uracil, 5-fluorouracil, thymine and cytosine and key intermediate with 6-chloropurine (5) as nucleobases were synthesized by a selective Mitsunobu reaction on the primary hydroxymethyl group in the presence of 5-endo-hydroxyl group. Adenine and 6-substituted adenine homonucleosides were obtained by the substitution of the 6-chlorine atom of the key intermediate 5 with ammonia and selected amines, and 6-methoxy- and 6-ethoxy substituted purine homonucleosides by reaction with the corresponding alkoxides. No derivatives appeared active against entero, yellow fever, chikungunya, and adeno type 1viruses. Two compounds (6j and 6d) had lower IC50 (15 ± 2 and 21 ± 4 µM) and compound 6f had an identical value of IC50 (28 ± 4 µM) to that of acyclovir, suggesting that the bicyclo[2.2.1]heptane skeleton could be further studied to find a candidate for sugar moiety of the nucleosides.
Subject(s)
Antiviral Agents/chemistry , Antiviral Agents/pharmacology , Glycosides/chemistry , Heptanes/chemistry , Nucleosides/chemistry , Nucleosides/pharmacology , Drug Design , Humans , Ligands , Microbial Sensitivity Tests , Molecular Conformation , Molecular Docking Simulation , Molecular Dynamics Simulation , Molecular Structure , Nucleosides/analogs & derivatives , Purines/chemistry , Spectrum Analysis , Structure-Activity Relationship , Sugars/chemistryABSTRACT
New nucleoside analogues with an optically active bicyclo[2.2.1]heptane skeleton as sugar moiety and 6-substituted adenine were synthesized by alkylation of 6-chloropurine intermediate. Thymine and uracil analogs were synthesized by building the pyrimidine ring on amine 1. X-ray crystallography confirmed an exo-coupling of the thymine to the ring and an L configuration of the nucleoside analogue. The library of compounds was tested for their inhibitory activity against influenza virus A∖California/07/09 (H1N1)pdm09 and coxsackievirus B4 in cell culture. Compounds 13a and 13d are the most promising for their antiviral activity against influenza, and compound 3c against coxsackievirus B4. Compounds 3b and 3g were tested for anticancer activity.
Subject(s)
Adenine Nucleotides/chemistry , Antineoplastic Agents/chemical synthesis , Antiviral Agents/chemical synthesis , Bridged Bicyclo Compounds/chemistry , Pyrimidine Nucleosides/chemistry , Animals , Antineoplastic Agents/pharmacology , Antiviral Agents/pharmacology , Cell Line, Tumor , Cell Survival/drug effects , Chlorocebus aethiops , Crystallography, X-Ray , Dogs , Drug Screening Assays, Antitumor , Enterovirus B, Human/drug effects , Humans , Influenza A Virus, H1N1 Subtype/drug effects , Madin Darby Canine Kidney Cells , Molecular Conformation , Structure-Activity Relationship , Vero CellsABSTRACT
An amine group was synthesized starting from an optically active bicyclo[2.2.1]heptane compound, which was then used to build the 5 atoms ring of a key 6-chloropurine intermediate. This was then reacted with ammonia and selected amines obtaining new adenine- and 6-substituted adenine conformationally constrained carbocyclic nucleoside analogues with a bicyclo[2.2.1]heptane skeleton in the sugar moiety. X-ray crystallography confirmed an exo-coupling of base to the ring and a L configuration of the nucleoside analogues. The compounds were tested for anticancer activity.
Subject(s)
Antineoplastic Agents/chemical synthesis , Heptanes/chemistry , Nucleosides/chemistry , Antineoplastic Agents/therapeutic use , Crystallography, X-Ray , Humans , Molecular Conformation , Molecular Structure , StereoisomerismABSTRACT
The essential oils (EOs) possess amazing properties explaining the interest for their applications in many essential domains. They also present the disadvantage of their chemical instability in the presence of air, light, moisture, and high temperatures. The paper focuses on two of the most known and used EOs, lavender and mint, respectively. The idea of the study was to protect them using the encapsulated systems. The originality of the work consists in the combination between the advantages of the molecular encapsulation of the EOs by cyclodextrins (CD) with the advantages offered by the sol-gel process. Original formulations have been processed by entrapping these essential oils in silica matrices obtained from a colloidal silica sol by the aqueous route of the sol-gel method. Another non-toxic ingredient, ß-cyclodextrin, able to form inclusion complexes (ICs) with the essential oils has been used. The characterization methods (chromatography, UV-vis, IR, and NMR spectroscopies) have evidenced the presence of the mentioned inclusion complexes. Due to their formation, which modifies the water solubility of the EOs, the chromatographic analysis was possible using water as solvent, which is a novelty in EOs determinations. Protected from both the cyclodextrin and silica matrix, the essential oils became more resistant versus the effects of the environment factors. Thus, the resulted powders can find applications in domains as agriculture, food industries, cosmetics, pharmaceutical, and medicine.
Subject(s)
Oils, Volatile/chemistry , Cyclodextrins/chemistry , Gels/chemistry , Lavandula/chemistry , Mentha/chemistry , Silicon Dioxide/chemistryABSTRACT
In the present study, we developed a method for the grape seed oil compositional characterisation using (1)H NMR spectroscopy directly applied on oils without sample derivatisation (as triglycerides). Using (1)H NMR spectroscopy data and systems of chemometric equations, we established the composition of grape seed oils on four classes of fatty acids. Spectral information from (1)H NMR and FT-IR spectroscopy was used to make the differences between grape seed oils and genuine common oils. Applying the PCA (Principal Component Analysis) method to the spectral information, it was evaluated the application potential in authenticity control of grape seed oils from common genuine oils (sunflower, soybean, linseed and rapeseed).
Subject(s)
Magnetic Resonance Spectroscopy/methods , Plant Oils/chemistry , Seeds/chemistry , Spectroscopy, Fourier Transform Infrared/methods , Vitis/chemistryABSTRACT
This paper reports a newly fabricated nanophyto-modified wound dressing with microbicidal and anti-adherence properties. Nanofluid-based magnetite doped with eugenol or limonene was used to fabricate modified wound dressings. Nanostructure coated materials were characterized by TEM, XRD, and FT-IR. For the quantitative measurement of biofilm-embedded microbial cells, a culture-based method for viable cell count was used. The optimized textile dressing samples proved to be more resistant to staphylococcal and pseudomonal colonization and biofilm formation compared to the uncoated controls. The functionalized surfaces for wound dressing seems to be a very useful tool for the prevention of wound microbial contamination on viable tissues.
ABSTRACT
Our purpose was obtaining and characterizing a complex composite system with multifunctional role: bone graft material and hyperthermia generator necessary for bone cancer therapy. The designed system was a magnetite enriched collagen/hydroxyapatite composite material, obtained by a co-precipitation method. Due to the applied electromagnetic field the magnetite will induce hyperthermia and cause tumoral cell apoptosis. The complex bone graft system was characterised by XRD, FTIR and SEM, while the hyperthermia was quantify by measuring the temperature increase due to the applied alternative electromagnetical field.
