RÉSUMÉ
Platinum-based chemotherapy is widely used for the treatment of different tumors but is associated with serious side effects, among which neuropathic pain. Carbonic anhydrase (CA, EC 4.2.1.1) inhibitors have recently been validated as therapeutic agents in neuropathic pain and as antitumor agents. We report the synthesis of new organochalcogenides bearing the benzensulfonamide moiety acting as potent inhibitors of several human CA isoforms and, in particular, against hCA II and VII endowed with potent neuropathic pain attenuating effects. Moreover, in combination with cisplatin or doxorubicin, some of the new CA inhibitors enhanced the effects of the anticancer drugs capability in counteracting breast cancer MCF7 cell viability. The concomitant anti-neuropathic pain and antiproliferative effects of the new chalcogenide-based CA inhibitors represent an innovative approach for the counteraction and management of side effects associated with clinically platinum drugs as antitumor agents.
Sujet(s)
Antinéoplasiques/pharmacologie , Inhibiteurs de l'anhydrase carbonique/pharmacologie , Carbonic anhydrases/métabolisme , Chalcogènes/pharmacologie , Cisplatine/pharmacologie , Névralgie/traitement médicamenteux , Administration par voie orale , Animaux , Antinéoplasiques/administration et posologie , Antinéoplasiques/composition chimique , Inhibiteurs de l'anhydrase carbonique/administration et posologie , Inhibiteurs de l'anhydrase carbonique/composition chimique , Prolifération cellulaire/effets des médicaments et des substances chimiques , Chalcogènes/synthèse chimique , Chalcogènes/composition chimique , Cisplatine/administration et posologie , Cisplatine/composition chimique , Relation dose-effet des médicaments , Tests de criblage d'agents antitumoraux , Humains , Isoenzymes/antagonistes et inhibiteurs , Isoenzymes/métabolisme , Cellules MCF-7 , Mâle , Souris , Structure moléculaire , Névralgie/induit chimiquement , Oxaliplatine , Stress oxydatif/effets des médicaments et des substances chimiques , Mesure de la douleur , Relation structure-activitéRÉSUMÉ
Differently substituted ß-hydroxy- and ß-amino dialkyl and alkyl-aryl tellurides and selenides have been prepared through ring-opening reactions of epoxides and aziridines with selenium- or tellurium-centered nucleophiles. The antioxidant properties and the cytotoxicity of such compounds have been investigated on normal human dermal fibroblasts. Most of the studied compounds exhibited a low cytotoxicity and a number of them proved to be non-toxic, not showing any effect on cell viability even at the highest concentration used (100 µM). The obtained results showed a significant antioxidant potential of the selected organotellurium compounds, particularly evident under conditions of exogenously induced oxidative stress. The antioxidant activity of selenium-containing analogues of active tellurides has also been evaluated on cells, highlighting that the replacement of Se with Te brought about a significant increase in the peroxidase activity.
Sujet(s)
Antioxydants/pharmacologie , Chalcogènes/pharmacologie , Dithiothréitol/métabolisme , Antioxydants/synthèse chimique , Antioxydants/composition chimique , Cellules cultivées , Chalcogènes/synthèse chimique , Chalcogènes/composition chimique , Relation dose-effet des médicaments , Humains , Structure moléculaire , Relation structure-activitéRÉSUMÉ
Approximately 90% of bladder carcinomas are of the urothelial carcinoma type, which are characterized by high rates of recurrence and predisposition to progress to invasive tumors, representing one of the most costly neoplasms for health systems. Intravesical chemotherapy is a standard for the treatment of non-invasive bladder cancer. However, chemotherapy is usually aggressive and cytotoxic, which increases the death rates caused by cancer. Heterocyclic compounds which exhibit favorable pharmacokinetic and pharmacodynamic properties may enhance drug affinity for a target protein by targeting the treatment. Thus, this work presents the synthesis, characterization, and in vitro biological evaluation of new antioxidant (inhibition of lipid peroxidation, scavenging of free radical DPPH, and thiol peroxidase-like activity) and antiproliferative chalcogenobiotin derivatives and tests them against bladder carcinoma 5637 cells. A prominent response was obtained for the selected compounds, with tellurium biotin derivatives displaying effective antioxidant and antiproliferative activity. The effective compounds also demonstrated no toxicity in in vitro or in vivo studies.
Sujet(s)
Antinéoplasiques/pharmacologie , Antioxydants/pharmacologie , Chalcogènes/pharmacologie , Tumeurs de la vessie urinaire/traitement médicamenteux , Vessie urinaire/effets des médicaments et des substances chimiques , Antinéoplasiques/synthèse chimique , Antinéoplasiques/composition chimique , Antioxydants/synthèse chimique , Antioxydants/composition chimique , Dérivés du biphényle/antagonistes et inhibiteurs , Lignée cellulaire tumorale , Prolifération cellulaire/effets des médicaments et des substances chimiques , Chalcogènes/synthèse chimique , Chalcogènes/composition chimique , Relation dose-effet des médicaments , Tests de criblage d'agents antitumoraux , Humains , Peroxydation lipidique/effets des médicaments et des substances chimiques , Structure moléculaire , Picrates/antagonistes et inhibiteurs , Relation structure-activité , Vessie urinaire/anatomopathologie , Tumeurs de la vessie urinaire/anatomopathologieRÉSUMÉ
A mild and general procedure for the difluoromethylation of organochalcogen compounds has been accomplished via sulfoxide and selenoxide-directed [3,3]-sigmatropic rearrangement/Haller-Bauer reaction with difluoroenoxysilanes. The reactions showed good functional group compatibility, wide substrate applicability, and facile scalability. The synthetic utility is highlighted by the iterative use of this protocol to construct multi-CF2H-containing chalcogenides and the late-stage modification of pharmaceuticals.
Sujet(s)
Chalcogènes/synthèse chimique , Hydrocarbures fluorés/composition chimique , Oxydes de sélénium/composition chimique , Silanes/composition chimique , Sulfoxydes/composition chimique , Chalcogènes/composition chimique , Structure moléculaire , StéréoisomérieRÉSUMÉ
The first total synthesis of the yellow pigment chalcitrin, a structurally distinct pulvinic acid dimer obtained from Chalciporous piperatus, has been achieved in 17 linear steps from commercially available materials. Key elements of the design include the use of a Au(I)-catalyzed Conia ene reaction and an N-heterocyclic carbene-mediated acyloin addition to rapidly fashion its unique polycyclic core, with the two high oxidation state side chains introduced in a single step via a late-stage double Stille coupling. Of note, many alternate designs based on differential final couplings failed, likely because of the hindered nature of the core. In addition, significant challenges in final natural product characterization in terms of matching NMR spectra were experienced; our studies reveal that the originally characterized material was its carboxylate salt form not its free acid.
Sujet(s)
Chalcogènes/composition chimique , Chalcogènes/synthèse chimique , Techniques de chimie synthétique , Dimérisation , CinétiqueRÉSUMÉ
A series of novel persistent room-temperature phosphorescence (pRTP) materials (PEPCz) obtained via a combination of chalcogen atoms (O, S, Se, and Te) and a carbazolyl moiety is reported. Single crystal structure analysis revealed that PEPCz had similar molecular conformations and almost identical crystal packing. Mechanistic study showed that the intramolecular electronic coupling between the chalcogen atoms and π-units was responsible for tunable pRTP. The PEPCz were used not only to realize graphic encryption, but also to fabricate pRTP sensors for H2O2 and TNT detection.
Sujet(s)
Carbazoles/composition chimique , Chalcogènes/composition chimique , Luminescents/composition chimique , Carbazoles/synthèse chimique , Chalcogènes/synthèse chimique , Peroxyde d'hydrogène/analyse , Luminescence , Luminescents/synthèse chimique , Modèles chimiques , Théorie quantique , Température , 2,4,6-Trinitro-toluène/analyseRÉSUMÉ
A chalcogen bond (ChB) is a σ-hole-based noncovalent interaction between a Lewis base and an electrophilic element of Group VI (O, S, Se, Te), which behaves as a Lewis acid. Recently, we demonstrated that halogen bond, the more familiar σ-hole-based interaction, is able to promote the enantioseparation of chiral compounds in HPLC environment. On this basis, an investigation to detect ChBs, functioning as stereoselective secondary interactions for HPLC enantioseparations, was started off and the results of this study are described herein. Our investigation also focused on the impact of the perfluorinated aromatic ring as a π-hole donor recognition site. For these purposes, seven atropisomeric fluorinated 3-arylthio-4,4'-bipyridines were designed, synthesized and used as potential ChB donors (ChBDs) with two cellulose-based chiral stationary phases (CSPs) containing carbonyl groups as ChB acceptors (ChBAs). In addition, one and two analogues lacking fluorine and sulphur, respectively, were prepared as terms of comparison. The design of the test analytes was computationally guided. In this regard, electrostatic potentials (EPs) associated with σ- and π-holes were computed and the atomic contributions to the sulphur EP maxima were derived using a molecular space partitioning in terms of Bader's atomic basins. This procedure is akin to the Bader-Gatti electron density source function (SF) decomposition, yet suitably extended to the EP field. For five 3-substituted-4,4'-bipyridines, thermodynamic parameters were derived from van't Hoff plots. Finally, the use of molecular dynamic (MD) simulation to model ChB in cellulose-analyte complexes was explored. Evidences that σ-hole and π-hole interactions can jointly drive HPLC enantioseparations through recognition sites generated by electronic charge depletion emerged from both experimental results and theoretical data.
Sujet(s)
Chalcogènes/composition chimique , Chromatographie en phase liquide à haute performance/méthodes , Halogénation , Pyridines/composition chimique , Pyridines/isolement et purification , Cellulose/composition chimique , Chalcogènes/synthèse chimique , Électrons , Entropie , Halogènes/composition chimique , Modèles linéaires , Simulation de dynamique moléculaire , Pyridines/synthèse chimique , Électricité statique , Stéréoisomérie , ThermodynamiqueRÉSUMÉ
Organic selenium and tellurium compounds are known for their broad-spectrum effects in a variety of experimental disease models. However, these compounds commonly display high toxicity and the molecular mechanisms underlying these deleterious effects have yet to be elucidated. Thus, the need for an animal model that is inexpensive, amenable to high-throughput analyses, and feasible for molecular studies is highly desirable to improve organochalcogen pharmacological and toxicological characterization. Herein, we use Caenorhabdtis elegans (C. elegans) as a model for the assessment of pharmacological and toxicological parameters following exposure to two 4-phenylchalcogenil-7-chloroquinolines derivatives (PSQ for selenium and PTQ for tellurium-containing compounds). While non-lethal concentrations (NLC) of PTQ and PSQ attenuated paraquat-induced effects on survival, lifespan and oxidative stress parameters, lethal concentrations (LC) of PTQ and PSQ alone are able to impair these parameters in C. elegans. We also demonstrate that DAF-16/FOXO and SKN-1/Nrf2 transcription factors underlie the mechanism of action of these compounds, as their targets sod-3, gst-4 and gcs-1 were modulated following exposures in a daf-16- and skn-1-dependent manner. Finally, in accordance with a disturbed thiol metabolism in both LC and NLC, we found higher sensitivity of trxr-1 worm mutants (lacking the selenoprotein thioredoxin reductase 1) when exposed to PSQ. Finally, our study suggests new targets for the investigation of organochalcogen pharmacological effects, reinforcing the use of C. elegans as a powerful platform for preclinical approaches.
Sujet(s)
Antioxydants/pharmacologie , Caenorhabditis elegans/effets des médicaments et des substances chimiques , Chalcogènes/pharmacologie , Composés organométalliques/pharmacologie , Composés organiques du sélénium/pharmacologie , Quinoléines/pharmacologie , Tellure/pharmacologie , Animaux , Antioxydants/synthèse chimique , Caenorhabditis elegans/génétique , Caenorhabditis elegans/croissance et développement , Caenorhabditis elegans/métabolisme , Protéines de Caenorhabditis elegans/génétique , Protéines de Caenorhabditis elegans/métabolisme , Chalcogènes/synthèse chimique , Protéines de liaison à l'ADN/génétique , Protéines de liaison à l'ADN/métabolisme , Facteurs de transcription Forkhead/génétique , Facteurs de transcription Forkhead/métabolisme , Régulation de l'expression des gènes , Longévité/effets des médicaments et des substances chimiques , Facteur-2 apparenté à NF-E2/génétique , Facteur-2 apparenté à NF-E2/métabolisme , Composés organométalliques/synthèse chimique , Composés organiques du sélénium/synthèse chimique , Oxydants/antagonistes et inhibiteurs , Oxydants/toxicité , Stress oxydatif , Paraquat/antagonistes et inhibiteurs , Paraquat/toxicité , Quinoléines/synthèse chimique , Transduction du signal , Superoxide dismutase/génétique , Superoxide dismutase/métabolisme , Facteurs de transcription/génétique , Facteurs de transcription/métabolismeRÉSUMÉ
The ß-cyclodextrin-assisted aqueous-exfoliation method was used to prepare transition-metal dichalcogenide (TMD) nanosheets, in a cheap, highly efficient, scalable and environmentally friendly manner. As study cases, MoS2 and ReS2 nanoflakes were prepared according to this method. Particularly, the effective exfoliation of ReS2 crystals in an aqueous environment was observed for the first time. Moreover, exfoliated nanomaterials can be readily utilized in hydrogen evolution reactions (HERs) as noble-metal-free catalysts. This work provides new opportunities for highly efficient exfoliation of TMDs and other 2D nanomaterials into few-layer nanosheets in aqueous media. Their production process showed high biocompatibility, broad applicability and excellent sustainability.
Sujet(s)
Chalcogènes/synthèse chimique , Disulfures/composition chimique , Molybdène/composition chimique , Nanostructures/composition chimique , Rhénium/composition chimique , Sulfures/composition chimique , Cyclodextrines bêta/composition chimique , Chalcogènes/composition chimique , Taille de particule , Propriétés de surface , Eau/composition chimiqueRÉSUMÉ
A new thorium monoalkyl complex, Th(CH2SiMe3)(L3) (L = MeC(NiPr)2) (2), undergoes insertion of chalcogen atoms resulting in a series of thorium chalcogenolate complexes, Th(ECH2SiMe3)(L3) (E = S, SS, Se, Te; 5-8). Complex 6 represents the first alkyl disulfide thorium species and illustrates the ability of 2 to undergo controllable, stoichiometric atom insertion. All complexes have been characterized by 1H and 13C NMR spectroscopy, FTIR, EA, and melting point, and in the case of 1, 2, and 4-8, X-ray crystallography. Insertion was achieved by balancing the thermodynamic driving force of chalcogenolate formation versus the BDE of the pnictogen-chalcogen bond in the transfer reagent. Utilizing Me3NO as an oxygen atom transfer reagent led to C-H activation and SiMe4 extrusion rather than oxygen atom insertion, resulting in the alkoxide complex Th(OCH2NMe2)(L3) (4).
Sujet(s)
Carbone/composition chimique , Chalcogènes/synthèse chimique , Composés organométalliques/composition chimique , Composés du thorium/synthèse chimique , Chalcogènes/composition chimique , Cristallographie aux rayons X , Modèles moléculaires , Conformation moléculaire , Composés organométalliques/synthèse chimique , Thermodynamique , Composés du thorium/composition chimiqueRÉSUMÉ
Recent research has revealed a gamut of interesting properties present in layered two-dimensional (2D) transition metal dichalcogenides (TMDCs) such as photoluminescence, comparatively high electron mobility, flexibility, mechanical strength and relatively low toxicity. The large surface to area ratio inherent in these materials also allows easy functionalization and maximal interaction with the external environment. Due to its unique physical and chemical properties, much work has been done in tailoring TMDCs through chemical functionalization for use in a diverse range of biomedical applications as biosensors, drug delivery carriers or even as therapeutic agents. In this review, current progress on the different types of TMDC functionalization for various biological applications will be presented and its future outlook will be discussed.
Sujet(s)
Technologie biomédicale/méthodes , Chalcogènes/composition chimique , Éléments de transition/composition chimique , Matériaux biocompatibles/synthèse chimique , Matériaux biocompatibles/composition chimique , Chalcogènes/synthèse chimiqueRÉSUMÉ
In this work, 27 novel hybrid derivatives containing diverse substituents with chalcogen atoms (selenium or sulfur) and several active heterocyclic scaffolds have been synthesized. Compounds were tested against two human cancer cells lines (MCF7 and PC-3) and a normal human mammary epithelial cell line (184B5) in order to determine their activity and selectivity against malignant cells. Ten compounds showed GI50 values below 10 µM in at least one of the cancer cell lines and six of them exhibited a selectivity index higher than 9. In general, selenium-containing compounds were more active than their corresponding sulfur analogs but we found some thiocyanate derivatives with comparable or higher activity and selectivity. Among the different substituents, the seleno- and thio-cyanate groups showed the most promising results. On the basis of their potent activity and high selectivity index, compounds 7e and 8f (containing a thiocyanate and a selenocyanate group, respectively) were selected for further biological evaluation. Both the compounds induced caspase-dependent cell death and cell cycle arrest in G2/M phase. In addition, these compounds do not violate any of the Lipinski's Rule of Five and thus possess good potential to become drugs, compound 7e being particularly promising.
Sujet(s)
Antinéoplasiques/composition chimique , Antinéoplasiques/pharmacologie , Chalcogènes/composition chimique , Chalcogènes/pharmacologie , Composés hétérocycliques/composition chimique , Antinéoplasiques/synthèse chimique , Points de contrôle du cycle cellulaire/effets des médicaments et des substances chimiques , Mort cellulaire/effets des médicaments et des substances chimiques , Lignée cellulaire tumorale , Prolifération cellulaire/effets des médicaments et des substances chimiques , Chalcogènes/synthèse chimique , Tests de criblage d'agents antitumoraux , Humains , Relation structure-activitéRÉSUMÉ
The advances in my laboratory for the past 20-25 years concerning the chemistry of chalcogen-containing heterocycles are reviewed. The intramolecular cyclization of the chalcogenols (-TeH, -SeH, -SH) into a triple bond or appropriate leaving group produced various chalcogen-containing heterocycles. The reactions of the obtained products were examined: the reactions of 1-benzo- and 2-benzopyrylium salts containing a tellurium or selenium element with several nucleophiles, including alkoxides, amines, the cyanide ion, an active methyl compound (acetone), Grignard reagents, copper reagents, and tin reagents, along with hydrogenation and hydrolysis reactions, provided corresponding chromes or isochromes having various functional groups at the 2- or 1-C position. Isothiocyanate and isoselenocyanate were used as chalcogen sources for the preparation of five- or six-membered heterocycles. In addition, double intramolecular cyclization, ring-expansion reactions, electrophilic cyclization and iodocyclization were also carried out.
Sujet(s)
Chalcogènes/composition chimique , Chalcogènes/synthèse chimique , Composés hétérocycliques/composition chimique , Composés hétérocycliques/synthèse chimique , Cyclisation , Réaction de cycloaddition , Soufre/composition chimiqueRÉSUMÉ
The cyclic dichalcogenides based on the bis(2-chalcogenoethyl)amide structure are latent N,S (SEA, chalcogen = S) or N,Se (SeEA, chalcogen = Se) acyl shift systems. The large difference in the reducing potential between SEA and SeEA dichalcogenides allows their sequential and selective activation by reduction. Based on these concepts, one-pot three or four peptide segment assembly processes were designed, facilitating access to branched or cyclic peptide scaffolds.
Sujet(s)
Amides/composition chimique , Chalcogènes/synthèse chimique , Peptides cycliques/synthèse chimique , Peptides/synthèse chimique , Chalcogènes/composition chimique , Cystéine/composition chimique , Structure moléculaire , Peptides/composition chimique , Peptides cycliques/composition chimiqueRÉSUMÉ
High sensitivity and specificity are two desirable features in biomedical imaging. Raman imaging has surfaced as a promising optical modality that offers both. Here we report the design and synthesis of a group of near-infrared absorbing 2-thienyl-substituted chalcogenopyrylium dyes tailored to have high affinity for gold. When adsorbed onto gold nanoparticles, these dyes produce biocompatible SERRS nanoprobes with attomolar limits of detection amenable to ultrasensitive in vivo multiplexed tumour and disease marker detection.
Sujet(s)
Chalcogènes/métabolisme , Agents colorants/métabolisme , Or/métabolisme , Composés hétérocycliques 3 noyaux/métabolisme , Nanoparticules métalliques , Analyse spectrale Raman/méthodes , Adsorption , Chalcogènes/synthèse chimique , Agents colorants/synthèse chimique , Composés hétérocycliques 3 noyaux/synthèse chimique , Propriétés de surfaceRÉSUMÉ
In this article we present the synthesis, characterization, and in vitro biological and biochemical activities of new chalcogenozidovudine derivatives as antioxidant (inhibition of TBARS in brain membranes and thiol peroxidase-like activity) as well as antitumoral agents in bladder carcinoma 5637. A prominent response was obtained for the selected chalcogenonucleosides, showing effective antioxidant and antitumoral activities.
Sujet(s)
Antinéoplasiques/composition chimique , Antioxydants/composition chimique , Chalcogènes/composition chimique , Tumeurs de la vessie urinaire/traitement médicamenteux , Zidovudine/composition chimique , Animaux , Antinéoplasiques/synthèse chimique , Antinéoplasiques/pharmacologie , Antioxydants/synthèse chimique , Antioxydants/pharmacologie , Apoptose/effets des médicaments et des substances chimiques , Lignée cellulaire tumorale , Chalcogènes/synthèse chimique , Chalcogènes/pharmacologie , Humains , Mâle , Rat Wistar , Substances réactives à l'acide thiobarbiturique/métabolisme , Vessie urinaire/effets des médicaments et des substances chimiques , Vessie urinaire/métabolisme , Vessie urinaire/anatomopathologie , Tumeurs de la vessie urinaire/métabolisme , Tumeurs de la vessie urinaire/anatomopathologie , Zidovudine/synthèse chimique , Zidovudine/pharmacologieRÉSUMÉ
A silver-mediated oxidative vinylic C-H bond sulfenylation of enamides was developed. This method is compatible with diaryl and dialkyl disulfides to deliver biologically precious chalcogenated olefins efficiently. A plausible non-chain radical mechanism was proposed for understanding this novel sulfenylation based on the mechanistic studies.
Sujet(s)
Alcènes/synthèse chimique , Chalcogènes/synthèse chimique , Disulfures/composition chimique , Argent/composition chimique , Alcènes/composition chimique , Catalyse , Chalcogènes/composition chimique , OxydoréductionRÉSUMÉ
We describe here a simple method for the synthesis of glycerol derivatives containing an organochalcogen unit (Se, Te and S) using NaBH4 and PEG-400 as a solvent. The new methodology was used to synthesize a range of new organochalcogen compounds in good yields. Furthermore, four of synthesized compounds were evaluated for their antioxidant activity using different assays, such as 2-azinobis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, nitric oxide (NO) and hydroxyl radical (OH) scavenging, ferric ion reducing antioxidant power (FRAP), ferrous ion chelating, superoxide dismutase-like activity and inhibition of linoleic acid lipid peroxidation. The new organotellurium 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j showed antioxidant activity and was more effective in inhibition of induced lipid peroxidation compared to solketal 4. Selenium and sulfur analogs 3a and 3m and solketal 4 did not present antioxidant effect. These findings suggest that 2,2-dimethyl-4-(phenyltellanylmethyl)-1,3-dioxolane 3 j is a promising antioxidant and that its activity is influenced by the presence of the tellurium atom on the structure.
Sujet(s)
Antioxydants/composition chimique , Antioxydants/pharmacologie , Chalcogènes/composition chimique , Chalcogènes/pharmacologie , Glycérol/composition chimique , Glycérol/pharmacologie , Antioxydants/synthèse chimique , Dérivés du biphényle/composition chimique , Chalcogènes/synthèse chimique , Piégeurs de radicaux libres/synthèse chimique , Piégeurs de radicaux libres/composition chimique , Piégeurs de radicaux libres/pharmacologie , Glycérol/synthèse chimique , Peroxydation lipidique/effets des médicaments et des substances chimiques , Composés organométalliques/synthèse chimique , Composés organométalliques/composition chimique , Composés organométalliques/pharmacologie , Picrates/composition chimiqueRÉSUMÉ
We report in this work an environmentally benign zinc mediated synthesis of aryl and benzyl phosphorochalcogenoates in ethanol within a short reaction time. In vitro antimicrobial study along with statistical analysis and seed germination assay were performed. These chalcogenophosphates possess strong antimicrobial activity against the reference strains. The antibacterial activity was determined against four standard strains (Bacilus subtilis, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa). The antifungal activity was evaluated against one fungal strain Candida albicans.
Sujet(s)
Anti-infectieux/composition chimique , Anti-infectieux/pharmacologie , Chalcogènes/composition chimique , Chalcogènes/pharmacologie , Phosphates/composition chimique , Phosphates/pharmacologie , Anti-infectieux/synthèse chimique , Bactéries/effets des médicaments et des substances chimiques , Infections bactériennes/traitement médicamenteux , Candida albicans/effets des médicaments et des substances chimiques , Candidose/traitement médicamenteux , Chalcogènes/synthèse chimique , Technologie de la chimie verte , Humains , Tests de sensibilité microbienne , Phosphates/synthèse chimiqueRÉSUMÉ
Copper(II) halide mediated cyclization of homopropargyl chalcogenides gave three types of chalcogenophene derivatives. Selective product formation was achieved by controlling solvent, temperature, and atmosphere. By using CuBr2 and 1,2-dichloroethane at room temperature under ambient atmosphere, 4-bromo dihydroselenophene derivatives were obtained, whereas CuBr2 and 1,2-dichloroethane at reflux gave selectively 2-substituted selenophenes. When 1,2-dichloroethane was replaced by dimethylacetamide, 3-halo-selenophenes were obtained exclusively. The versatility of chalcogenophenes was also studied by reaction of 3-haloselenophenes with terminal alkynes under Sonogashira conditions affording the cross-coupled products. In addition, the reaction of 3-haloselenophenes with boronic acids gave the corresponding Suzuki-type products in good yields.