Browse
Submit Data
Databases
API
Help

Dataset Information

13 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds.

ABSTRACT: A series of novel thiourea and amide liquid crystals containing 5-membered isoxazoline and isoxazole rings were synthetized and the liquid crystal properties studied. Thioureas were obtained using a condensation reaction of benzoyl chlorides, arylamines and ammonium thiocyanate. The amides, on the other hand, were the byproduct of a quantitative reaction which used potassium cyanate as the starting material. Thiourea and amide derivatives were predominantly SmA mesophase inductors. A nematic mesophase was observed only for thioureas and amides containing an isoxazole ring. Additionaly, the liquid crystal behavior was also dependent on the relative position of nitrogen and oxygen atoms on the 5-membered heterocycle.

SUBMITTER: Goncalves IL

PROVIDER: S-EPMC7034240 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

The use of isoxazoline and isoxazole scaffolding in the design of novel thiourea and amide liquid-crystalline compounds.

Gonçalves Itamar L IL da Rosa Rafaela R RR Eifler-Lima Vera L VL Merlo Aloir A AA

Beilstein journal of organic chemistry 20200206

A series of novel thiourea and amide liquid crystals containing 5-membered isoxazoline and isoxazole rings were synthetized and the liquid crystal properties studied. Thioureas were obtained using a condensation reaction of benzoyl chlorides, arylamines and ammonium thiocyanate. The amides, on the other hand, were the byproduct of a quantitative reaction which used potassium cyanate as the starting material. Thiourea and amide derivatives were predominantly SmA mesophase inductors. A nematic mes ...[more]

PMID: 32117474

Similar Datasets

Tetrahydroquinoline-Isoxazole/Isoxazoline Hybrid Compounds as Potential Cholinesterases Inhibitors: Synthesis, Enzyme Inhibition Assays, and Molecular Modeling Studies.

Project description:A series of 44 hybrid compounds that included in their structure tetrahydroquinoline (THQ) and isoxazole/isoxazoline moieties were synthesized through the 1,3-dipolar cycloaddition reaction (1,3-DC) from the corresponding N-allyl/propargyl THQs, previously obtained via cationic Povarov reaction. In vitro cholinergic enzymes inhibition potential of all compounds was tested. Enzyme inhibition assays showed that some hybrids exhibited significant potency to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Especially, the hybrid compound 5n presented the more effective inhibition against AChE (4.24 µM) with an acceptable selectivity index versus BChE (SI: 5.19), while compound 6aa exhibited the greatest inhibition activity on BChE (3.97 µM) and a significant selectivity index against AChE (SI: 0.04). Kinetic studies were carried out for compounds with greater inhibitory activity of cholinesterases. Structure-activity relationships of the molecular hybrids were analyzed, through computational models using a molecular cross-docking algorithm and Molecular Mechanics/Generalized Born Surface Area (MM/GBSA) binding free energy approach, which indicated a good correlation between the experimental inhibition values and the predicted free binding energy.

| S-EPMC6981637 | biostudies-literature

Structure and thermal transitions in a biomedically relevant liquid crystalline poly(ester amide).

Project description:There is still a need to develop bioresorbable polymers with high strength and high modulus for load-bearing biomedical applications. Here we investigate the liquid crystalline structural features of poly(desaminotyrosyl-tyrosine dodecyl dodecanedioate), poly(DTD DD), a new bioresorbable poly(ester amide) that is currently studied in vivo as a slow-degrading implantable biomaterial for load bearing applications. Thermally induced structural changes in poly(DTD DD) were studied using simultaneously differential scanning calorimetry (DSC) and X-ray scattering. The hexatic SmB organization of the polymer chains that exists at room temperature becomes progressively disordered upon heating, changing into a SmF phase and then into a smectic C phase at 60°C before turning into a free flowing melt at 130°C. X-ray scattering data and thermal analysis indicate the presence of a 2D ordered structure in the polymer melt. A structural model with an interesting 3-fold symmetry in the packing of the side chains around the rigid aromatic main chain, and the packing of these chains into fibrils is proposed. The liquid crystalline behavior of poly(DTD DD) makes it possible to melt process it at low temperatures without thermal degradation. This is a noteworthy advantage for the use of poly(DTD DD) as a high strength, readily processable, yet biodegradable polymer.

| S-EPMC6827981 | biostudies-literature

Diastereoselective additive trifluoromethylation/halogenation of isoxazole triflones: synthesis of all-carbon-functionalized trifluoromethyl isoxazoline triflones.

Project description:Highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives featuring a triflyl (SO2CF3) group at the 4-position were successfully synthesized via diastereoselective trifluoromethylation and halogenation of isoxazole triflones using the Ruppert- Prakash reagent. The trifluoromethylation is quite general in terms of the substrates including 3,5-diaryl isoxazole triflones and 3-aryl-5-styrylisoxazole triflones to provide products in high yields with excellent diastereoselectivities. The highly functionalized 5-trifluoromethyl-2-isoxazoline derivatives are expected to be a new class of antiparasiticides. Thus the triflyl group both activates isoxazoles and the 4-postion of CF3 adducts, and has a potential biological function.

| S-EPMC3943607 | biostudies-literature

N,N-Dimethyl-3-phenyl-isoxazole-5-carbox-amide.

Project description:In the title compound, C12H12N2O2, synthesized by ammonolysis of 3-phenyl-isoxazole-5-carbonyl chloride in di-chloro-methane, the dihedral angle between the isoxazole ring and the phenyl ring is 14.05?(7)°. In the crystal, centrosym-metrically related mol-ecules are linked into dimers by pairs of C-H?O hydrogen bonds, generating rings of graph-set motif R 2 (2)(10).

| S-EPMC3914115 | biostudies-literature

Design, Synthesis, and Bioactivity Evaluation of Novel Isoxazole-Amide Derivatives Containing an Acylhydrazone Moiety as New Active Antiviral Agents.

Project description:As a continuation of our efforts to discover and develop "me-better" active molecules, in this study, a series of novel isoxazole-amide derivatives containing an acylhydrazone moiety were synthesized and evaluated for their antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Antiviral bioassays indicated that some of the target compounds exhibited better in vivo antiviral activities against TMV and CMV than those of Ningnanmycin (NNM). Especially, the compound 7t exhibited the best curative, protection, and inactivation activities against TMV and CMV which were superior to those of NNM. Meanwhile, our present work also revealed that compound 7t could enhance the defense-related enzyme activity and increase the chlorophyll content in tobacco leaves to induce resistance and enhance plant tolerance to TMV infection.

| S-EPMC6832660 | biostudies-literature

Design rules for liquid crystalline electrolytes for enabling dendrite-free lithium metal batteries.

Project description:Dendrite-free electrodeposition of lithium metal is necessary for the adoption of high energy-density rechargeable lithium metal batteries. Here, we demonstrate a mechanism of using a liquid crystalline electrolyte to suppress dendrite growth with a lithium metal anode. A nematic liquid crystalline electrolyte modifies the kinetics of electrodeposition by introducing additional overpotential due to its bulk-distortion and anchoring free energy. By extending the phase-field model, we simulate the morphological evolution of the metal anode and explore the role of bulk-distortion and anchoring strengths on the electrodeposition process. We find that adsorption energy of liquid crystalline molecules on a lithium surface can be a good descriptor for the anchoring energy and obtain it using first-principles density functional theory calculations. Unlike other extrinsic mechanisms, we find that liquid crystals with high anchoring strengths can ensure smooth electrodeposition of lithium metal, thus paving the way for practical applications in rechargeable batteries based on metal anodes.

| S-EPMC7604459 | biostudies-literature

Synthesis and Biological Evaluation of Novel Hybrid Molecules Containing Purine, Coumarin and Isoxazoline or Isoxazole Moieties.

Project description:The 1,3-dipolar cycloaddition reactions of nitrile oxides formed in situ (in the presence of NCS and Et3N) from the oximes of (purin-9-yl)acetaldehyde or (coumarinyloxy)acetaldehyde with allyloxycoumarins or 9-allylpurines, respectively resulted in 3,5-disubstituted isoxazolines. The similar reactions of propargyloxycoumarins or 9-propargylpurines led to 3,5-disubstituted isoxazoles by treatment with PIDA and catalytic amount of TFA.The new compounds were tested in vitro as antioxidant agents and inhibitors of soybean lipoxygenase LO, AChE and MAO-B.The majority of the compounds showed significant hydroxyl radical scavenging activity. Compounds 4k and 4n presented LO inhibitory activity.Compound 13e presents an antioxidant significant profile combining anti-LO, anti-AChE and anti-MAO-B activities.

| S-EPMC5748833 | biostudies-other

Liquid Crystalline Copolymers Containing Sulfonic and Light-Responsive Groups: From Molecular Design to Conductivity.

Project description:In the search for novel smart multifunctional liquid crystalline materials, we report the synthesis, thermal and structural characterisation, and the conductivity, of a set of new block and statistical copolymers, containing light-responsive mesogenic groups (MeOAzB), polar sulfonic acids (AMPS), and methyl(methacrylate) groups (MMA). By using a cascade of reversible addition-fragmentation chain polymerisations, RAFT, we have tailored different side-chain polymeric structures by controlling monomer composition (MeOAzB/AMPS/MMA) and configuration. We have yielded simultaneous liquid crystalline behaviour and appreciable conductivity in polymers with low concentrations of polar acid groups, by the formation of smectic phases in narrow aggregates. The light-responsiveness of the polymers, via reversible trans-to-cis photoisomerization of azobenzene groups, and the local activation of conductivity at relatively low temperatures, opens the possibility to prepare polymer electrolytes for energy conversion and storage, whose conductivity could be controlled and optimised by external stimuli, including light irradiation.

| S-EPMC7321325 | biostudies-literature

Solid Phase Synthesis of Isoxazole and Isoxazoline-carboxamides via [2+3]-Dipolar Cycloaddition Using Resin-bound Alkynes or Alkenes.

Project description:An efficient approach for the parallel solid phase synthesis of isoxazole and isoxazoline derivatives has been developed. The isoxazoles and isoxazolines were constructed through a 1,3-dipolar cycloaddition reaction of nitrile oxides, with resin-bound alkynes or alkenes. The cycloaddition reaction conditions performed on solid phase supports was optimized, and an array of resin bound carboxylic acid building blocks were utilized for distinct conversions. This methodology presents a new alternative to the diversity oriented synthesis of disubstituted isoxazoles and isoxazolines different from existing routes which are limited in structural diversity.

| S-EPMC3376396 | biostudies-literature

Analysis of amide compounds in different parts of Piper ovatum Vahl by high-performance liquid chromatographic.

Project description:BACKGROUND:Piper ovatum (Piperaceae) has been used in traditional medicine for the treatment of inflammations and as an analgesic. Previous studies have showed important biological activities of the extracts and amides from P. ovatum leaves. OBJECTIVE:In this study, a high-performance liquid chromatographic (HPLC) method was developed and validated for quantitative determination of the amides in different parts of Piper ovatum. MATERIALS AND METHODS:The analysis was carried out on a Metasil ODS column (150 × 4.6 mm, 5?m) at room temperature. HPLC conditions were as follows: acetonitrile (A), and water (B), 1.0% acetic acid. The gradient elution used was 0-30 min, 0-60% A; 30-40 min, 60% A. Flow rate used was 1.0mL/min, and detection at 280nm. RESULTS:The validation using piperlonguminine, as the standard, demonstrated that the method shows linearity (linear correlation coefficient = 0.998), precision (relative standard deviation <5%) and accuracy (mean recovery = 103.78%) in the concentration range 31.25 - 500?g/mL. The limit of detection and quantification were 1.21 and 4.03?g/mL, respectively. This method allowed the identification and quantification of piperlonguminine and piperovatine in the hydroethanolic extracts of P. ovatum obtained from the leaves, stems and roots. All the extracts showed the same chromatographic profile. The leaves and roots contained the highest concentrations of piperlonguminine and the stems and leaves showed the most concentrations of piperovatine. CONCLUSION:This HPLC method is suitable for routine quantitative analysis of amides in extracts of Piper ovatum and phytopharmaceuticals containing this herb.

| S-EPMC3807989 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data