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An isoxazole strategy for the synthesis of 4-oxo-1,4-dihydropyridine-3-carboxylates.

ABSTRACT: A method has been developed for the preparation of 2-alkyl-6-aryl-, 2-aryl-6-aryl and 2,6-diaryl-5-aryl/hetaryl-substituted methyl 4-oxo-1,4-dihydropyridine-3-carboxylates by Mo(CO)₆-mediated ring expansion of methyl 2-(isoxazol-5-yl)-3-oxopropanoates. The high reactivity of 4-oxo-1,4-dihydropyridine-3-carboxylates synthesized provide easy access to 2,4,6-triaryl-substituted and 1,2,5,6-tetrasubstituted nicotinates.

SUBMITTER: Zanakhov TO

PROVIDER: S-EPMC9235835 | biostudies-literature |

REPOSITORIES: biostudies-literature

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First Organocatalytic Asymmetric Synthesis of 1-Benzamido-1,4-Dihydropyridine Derivatives.

Project description:Preliminary results concerning the first asymmetric synthesis of highly functionalized 1-benzamido-1,4-dihydropyridine derivatives via the reaction of hydrazones with alkylidenemalononitriles in the presence of ?-isocupreidine catalyst are reported. The moderate, but promising, enantioselectivity observed (40?54% ee), opens the door to a new area of research for the asymmetric construction of new chiral 1,4-dihydropyridine derivatives, whose enantioselective catalytic preparation are still very limited. Moreover, the use of hydrazones for the enantioselective construction of chiral 1,4-dihydropyridines has been overlooked in the literature so far. Therefore, our research represents a pivotal example in this field which remains still unexplored.

| S-EPMC6222298 | biostudies-literature

4,4'-Bipyridinium bis-(μ-4-oxo-1,4-dihydropyridine-2,6-dicarboxyl-ato)bis-[aqua-hydroxido-anti-monate(III)] dihydrate.

Project description:The title compound, (C(10)H(10)N(2))[Sb(2)(C(7)H(2)NO(5))(2)(OH)(2)(H(2)O)(2)]·2H(2)O, consists of a binuclear anion, a diprotonated 4,4'-bipyridinium cation and two uncoordinated water mol-ecules. Each Sb(III) atom is six-coordinated by one chelating 4-oxidopyridine-2,6-dicarboxyl-ate ligand, one water mol-ecule, one OH group and one bridging O atom from a neighboring carboxyl-ate group in a distorted penta-gonal-pyramidal geometry, with the OH group at the apical position. The two pyridine rings in the bipyridinium cation are twisted with respect to each other, making a dihedral angle of 22.7 (1)°. The cations are connected to the anions by N-H⋯O hydrogen bonds, forming a chain. The coordinated water mol-ecules form hydrogen bonds with the oxido O atoms of the anion, building a two-dimensional sheet, which is further connected into a three-dimensional structure by O-H⋯O and C-H⋯O hydrogen bonds and C=O⋯π inter-actions [O⋯centroid distances = 3.1785 (17), 3.4737 (19) and 3.5685 (19) Å].

| S-EPMC2983914 | biostudies-literature

Calcined Layered Double Hydroxides: Catalysts for Xanthene, 1,4-Dihydropyridine, and Polyhydroquinoline Derivative Synthesis.

Project description:This work is generally focused on the synthesis of NiFeTi-layered double hydroxides (LDHs) using a hydrothermal route, which were calcined at various temperatures (varying from 200 to 600 °C). The synthesized materials were physicochemically characterized. X-ray diffraction results revealed the loss of the layered structure on calcination resulting in the formation of layered double oxides (LDOs) or mixed metal oxides, which was also supported by Fourier transform infrared studies. Scanning electron microscopy results also show loss of the layered structure and the creation of LDOs on increasing the temperature. These LDOs were tested as the catalysts for the synthesis of biologically significant xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives. Among all, NiFeTi LDH calcined at 600 °C proved to be the best catalyst for the synthesis of these derivative compounds under optimized conditions. The advantages obtained were excellent yields in a lesser reaction time. Stability and reusability were also assessed; the catalyst was stable even after five cycles. Furthermore, the memory effect of the obtained NiFeTi CLDH calcined at 600 °C confirms that the material so formed is a calcined state of LDH itself. High catalytic efficiency, easy fabrication, and recycling ability of NiFeTi CLDH calcined at 600 °C make it a potential catalyst for the synthesis of xanthene, 1,4-dihydropyridine, and polyhydroquinoline derivatives.

| S-EPMC7331214 | biostudies-literature

Organocatalyzed enantioselective synthesis of 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylates.

Project description:The organocatalyzed enantioselective synthesis of biologically active 2-amino-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate derivatives was achieved using bifunctional cinchona alkaloids as the catalysts. Using quinine thiourea as the catalyst, the tandem Michael addition-cyclization reaction between 1,3-cyclohexanediones and alkylidenecyanoacetate derivatives gives the desired products in high yields (up to 92%) and good ee values (up to 82%).

| S-EPMC3212733 | biostudies-literature

Intramolecular hydrogen bonds in 1,4-dihydropyridine derivatives.

Project description:1,4-Dihydropyridine (1,4-DHP) derivatives have been synthesized and characterized by 1H, 13C, 15N nuclear magnetic resonance (NMR) spectroscopy, secondary proton/deuterium 13C isotope shifts, variable temperature 1H NMR experiments and quantum-chemical calculation. The intramolecular hydrogen bonds NH⋯O=C and CH⋯O=C in these compounds were established by NMR and quantum-chemical studies The downfield shift of the NH proton, accompanied by the upfield shift of the 15N nuclear magnetic resonance signals, the shift to the higher wavenumbers of the NH stretching vibration in the infrared spectra and the increase of the 1J(15N,1H) values may indicate the shortening of the N-H bond length upon intramolecular NH⋯O=C hydrogen bond formation.

| S-EPMC6030305 | biostudies-literature

Novel 1,4-Dihydropyridine Derivatives as Mineralocorticoid Receptor Antagonists.

Project description:The mineralocorticoid receptor (MR) belongs to the steroid receptor subfamily of nuclear receptors. MR is a transcription factor key in regulating blood pressure and mineral homeostasis. In addition, it plays an important role in a broad range of biological and pathological conditions, greatly expanding its interest as a pharmacological target. Non-steroidal MR antagonists (MRAs) are of particular interest to avoid side effects and achieve tissue-specific modulation of the receptor. The 1,4-dihydropyridine (1,4-DHP) ring has been identified as an appropriate scaffold to develop non-steroidal MRAs. We report the identification of a novel series of 1,4-DHP that has been guided by structure-based drug design, focusing on the less explored DHP position 2. Interestingly, substituents at this position might interfere with MR helix H12 disposition, which is essential for the recruitment of co-regulators. Several of the newly synthesized 1,4-DHPs show interesting properties as MRAs and have a good selectivity profile. These 1,4-DHPs promote MR nuclear translocation with less efficiency than the natural agonist aldosterone, which explains, at least in part, its antagonist character. Molecular dynamic studies are suggestive of several derivatives interfering with the disposition of H12 in the agonist-associated conformation, and thus, they might stabilize an MR conformation unable to recruit co-activators.

| S-EPMC9917360 | biostudies-literature

Fluorescent probes of the isoxazole-dihydropyridine scaffold: MDR-1 binding and homology model.

Project description:Isoxazole-1,4-dihydropyridines (IDHPs) were tethered to fluorescent moieties using double activation via a lanthanide assisted Weinreb amidation. IDHP-fluorophore conjugate 3c exhibits the highest binding to date for IDHPs at the multidrug-resistance transporter (MDR-1), and IDHP-fluorophore conjugates 3c and 7 distribute selectively in SH-SY5Y cells. A homology model for IDHP binding at MDR-1 is presented which represents our current working hypothesis.

| S-EPMC3987963 | biostudies-literature

Green approach for synthesis of bioactive Hantzsch 1,4-dihydropyridine derivatives based on thiophene moiety via multicomponent reaction.

Project description:A novel green and efficient one-pot multicomponent reaction of dihydropyridine derivatives was reported as having good to excellent yield. In the presence of the catalyst ceric ammonium nitrate (CAN), different 1,3-diones and same starting materials as 5-bromothiophene-2-carboxaldehyde and ammonium acetate were used at room temperature under solvent-free condition for the Hantzsch pyridine synthesis within a short period of time. All compounds were evaluated for their in vitro antibacterial and antifungal activity and, interestingly, we found that 5(b-f) show excellent activity compared with Ampicillin, whereas only the 5e compound shows excellent antifungal activity against Candida albicans compared with griseofulvin. The cytotoxicity of all compounds has been assessed against breast tumour cell lines (BT-549), but no activity was found. The X-ray structure of one such compound, 5a, viewed as a colourless block crystal, corresponded accurately to a primitive monoclinic cell.

| S-EPMC5493906 | biostudies-literature

Synthesis of efficient cobalt-metal organic framework as reusable nanocatalyst in the synthesis of new 1,4-dihydropyridine derivatives with antioxidant activity.

Project description:Efficient cobalt-metal organic framework (Co-MOF) was prepared via a controllable microwave-assisted reverse micelle synthesis route. The products were characterized by SEM image, N2 adsorption/desorption isotherm, FTIR spectrum, and TG analysis. Results showed that the products have small particle size distribution, homogenous morphology, significant surface area, and high thermal stability. The physicochemical properties of the final products were remarkable compared with other MOF samples. The newly synthesized nanostructures were used as recyclable catalysts in the synthesis of 1,4-dihydropyridine derivatives. After the confirmation of related structures, the antioxidant activity of derivatives based on the DPPH method was evaluated and the relationship between structures and antioxidant activity was observed. In addition to recyclability, the catalytic activity of Co-MOF studied in this research has remarkable effects on the synthesis of 1,4 dihydropyridine derivatives.

| S-EPMC9493035 | biostudies-literature

Design of 1,4-Dihydropyridine Hybrid Benzamide Derivatives: Synthesis and Evaluation of Analgesic Activity and Their Molecular Docking Studies.

Project description:PurposeThis study aims to determine the analgesic activity of 1,4-dihydropyridine hybrid benzamide derivatives. These hybrid derivatives were synthesized, and their analgesic activity was studied. The synthesis method applied was a one-step reaction involving a green chemistry approach.MethodsThe compounds were prepared via the amination method with a yield ranging between 82% and 93%. The title compounds were confirmed by means of IR, 1H and 13C NMR, and mass spectral analyses. The pharmacological activity of all the synthesized compounds was evaluated, and the analgesic activities were monitored in vivo (by tail immersion methods), with a digital analgesiometer. The drug response and damage of tail ata concentration of 10 mg/kg were measured by tail-flicking latency.ResultsThe activity of compound 2c (81.35% activity at 5mg/kg) can be correlated with its salicylamidemoiety (13.99% activity at 5mg/kg), and diclofenac showed comparable activity (79.21% activity at 5mg/kg reference drugs). Compound 2c has a higher potential to inhibit COX proteins compared to diclofenac. The drug-like nature of the molecule 2c corresponds to its ADME properties.ConclusionIn this study, all the synthesized compounds were found to possess significant analgesic activities; particularly, the performance of compound 2c is excellent. Thus, the preparative method described is an apt route for developing novel therapeutic formulations.

| S-EPMC9699661 | biostudies-literature

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