Browse
Submit Data
Databases
API
Help

Dataset Information

9 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Ultrasound-promoted greener synthesis of novel trifurcate 3-substituted-chroman-2,4-dione derivatives and their drug-likeness evaluation.

ABSTRACT: An efficient and convenient approach for one-pot synthesis of 3-substituted chroman-2,4-diones via a three-component reaction of aromatic aldehydes, 4-hydroxy-coumarins and diverse pyrazolone derivatives was described. The combinatorial synthesis for this methodology was achieved by applying ultrasound irradiation in the absence of activator while making use of water as green solvent. Additionally, novel chroman-2,4-dione derivatives attached to an edaravone moiety represent an exploitable source of brand new anticancer agents. In comparison with conventional methods, experimental simplicity, good functional group tolerance, excellent yields, short routine, and atom efficiency are prominent features of this sonocatalyzed procedure.

SUBMITTER: Liang C

PROVIDER: S-EPMC6268048 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Ultrasound-promoted greener synthesis of novel trifurcate 3-substituted-chroman-2,4-dione derivatives and their drug-likeness evaluation.

Liang Chengyuan C Jiang Hailong H Zhou Zhiguang Z Lei Dong D Xue Yu Y Yao Qizheng Q

Molecules (Basel, Switzerland) 20121128 12

An efficient and convenient approach for one-pot synthesis of 3-substituted chroman-2,4-diones via a three-component reaction of aromatic aldehydes, 4-hydroxy-coumarins and diverse pyrazolone derivatives was described. The combinatorial synthesis for this methodology was achieved by applying ultrasound irradiation in the absence of activator while making use of water as green solvent. Additionally, novel chroman-2,4-dione derivatives attached to an edaravone moiety represent an exploitable sourc ...[more]

PMID: 23192190

Similar Datasets

3-[2-(5-tert-Butyl-1,2-oxazol-3-yl)hydrazinyl-idene]chroman-2,4-dione.

Project description:In the title compound, C(16)H(15)N(3)O(4), the dihedral angle between the chromane and isoxazole rings [r.m.s. deviations = 0.042 and 0.007?Å, respectively] is 20.33?(12)°. The mol-ecular geometry is stabilized by an intra-molecular N-H?O hydrogen bond. In the crystal, N-H?O hydrogen bonds generate chains along the c-axis direction. The crystal studied was a non-morohedral twin.

| S-EPMC3569789 | biostudies-literature

Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent.

Project description:The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent molecule and derivative and explained from a structural point of view.

| S-EPMC6393868 | biostudies-literature

Design, synthesis, biological evaluation and molecular docking studies of novel 3-substituted-5-[(indol-3-yl)methylene]-thiazolidine-2,4-dione derivatives.

Project description:Various thiazolidine-2,4-dione derivatives 3a-l possessing indole moiety were designed, synthesized using appropriate conventional heating as well as microwave irradiation methods. All the synthesized compounds were characterized physically and spectrally. The compounds were evaluated for in vitro antibacterial activity, in vitro antioxidant activity and in vivo hypoglycemic activity in relation to the standard drugs. Most of the new compounds exhibited moderate activity and some showed considerable activity. Molecular docking studies were carried out using AutoDock software and revealed that compound 3b has significant binding interaction with PPAR? receptor compared with the standard ligand Rosiglitazone.

| S-EPMC6154471 | biostudies-literature

Synthesis of thiazolidine-2,4-dione derivatives: anticancer, antimicrobial and DNA cleavage studies.

Project description:In the search of efficient anticancer agents, here, new 5-(4-alkylbenzyledene)thiazolidine-2,4-dione derivatives (5a-g) have been successfully synthesized and characterized and are evaluated for anticancer and antimicrobial activities using DNA cleavage studies. In vitro studies on anticancer activity of compound 5d (NSC: 768619/1) was done against the full panel of 60 human tumor cell lines. The five-level dose activity results revealed that, the compound 5d was active against all the cell lines, it has shown potential activity against leukemia SR (GI50: 2.04 ?M), non-small cell lung cancer NCI-H522 (GI50: 1.36 ?M), colon cancer COLO 205 (GI50: 1.64 ?M), CNS cancer SF-539 (GI50: 1.87 ?M), melanoma SK-MEL-2 (GI50: 1.64 ?M), ovarian cancer OVCAR-3 (GI50: 1.87 ?M), renal cancer RXF 393 (GI50: 1.15 ?M), prostate cancer PC-3 (GI50: 1.90 ?M), and breast cancer MDA-MB-468(GI50: 1.11 ?M). DNA cleavage studies revealed that at 50 ?g/mL concentration, partial DNA digestion was observed and when the concentration is increasing to threefold (150 ?g/mL), complete linear DNA digestion and partial supercoiled DNA digestion was observed. Further antimicrobial studies indicate that all the synthesized compounds except compound 5a possess prominent activity against all the screened microbial species. This study throws a ray of light in the field of anticancer drugs.

| S-EPMC5026645 | biostudies-literature

Synthesis and evaluation of substituted chroman-4-one and chromone derivatives as sirtuin 2-selective inhibitors.

Project description:A series of substituted chromone/chroman-4-one derivatives has been synthesized and evaluated as novel inhibitors of SIRT2, an enzyme involved in aging-related diseases, e.g., neurodegenerative disorders. The analogues were efficiently synthesized in a one-step procedure including a base-mediated aldol condensation using microwave irradiation. The most potent compounds, with inhibitory concentrations in the low micromolar range, were substituted in the 2-, 6-, and 8-positions. Larger, electron-withdrawing substituents in the 6- and 8-positions were favorable. The most potent inhibitor of SIRT2 was 6,8-dibromo-2-pentylchroman-4-one with an IC(50) of 1.5 ?M. The synthesized compounds show high selectivity toward SIRT2 over SIRT1 and SIRT3 and represent an important starting point for the development of novel SIRT2 inhibitors.

| S-EPMC3426190 | biostudies-literature

Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives.

Project description:A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC50 values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.

| S-EPMC6968685 | biostudies-literature

Design, synthesis, in silico studies and biological evaluation of 5-((<i>E</i>)-4-((<i>E</i>)-(substituted aryl/alkyl)methyl)benzylidene)thiazolidine-2,4-dione derivatives.

Project description:BackgroundLooking at the extensive biological potential of thiazolidine-2,4-dione (TZD) moiety, a new series of thiazolidine-2,4-dione analogues was synthesized. Different spectral techniques (1H-NMR, IR, MS etc.) were used to confirm the chemical structures of the synthesized analogues. These synthesized compounds were screened for their antioxidant and antimicrobial potential.Results and discussionThe antimicrobial screening was carried out against selected strains of fungi and bacteria using serial tube dilution method. The antioxidant potential was assessed using stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging method. Further, the interaction between synthesized thiazolidine-2,4-dione compounds and DNA gyrase was explored using molecular docking studies. Various ADME parameters were also studied to evaluate the drug likeness of the synthesized compounds.ConclusionIn antimicrobial evaluation, the compounds 4, 9, 11, 12, 13, 15 and 16 displayed promising activity against selected strains of microbes. Antioxidant evaluation found compound 6 having IC50 = 9.18 μg/mL to be the most potent compound in the series. The molecular docking study revealed compounds 4 (dock score = - 4.73) and 7 (dock score = - 4.61) with decent docking score, possess good interaction inside the ATP binding pocket of DNA gyrase and therefore can be used as lead structure for further optimizing into potent antimicrobial molecule.

| S-EPMC7110766 | biostudies-literature

Synthesis, ?-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives.

Project description:A series of novel thiazolidine-2,4-dione or rhodanine derivatives (5a-5k, 6a-6k) were synthesized and evaluated for their ?-glucosidase inhibitory activity. The majority of compounds exhibited potent inhibitory activity in the range of 5.44 ± 0.13 to 50.45 ± 0.39 ?M, when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 ?M). Among the compounds in the series, compounds 5k, 6a, 6b, 6e, 6h and 6k showed potent inhibitory potential with IC50 values of 20.95 ± 0.21, 16.11 ± 0.19, 7.72 ± 0.16, 7.91 ± 0.17, 6.59 ± 0.15 and 5.44 ± 0.13 ?M, respectively. Compound 6k (IC50 = 5.44 ± 0.13 ?M), containing chloro and rhodanine groups at the 2- and 4-positions of the phenyl ring respectively, was found to be the most active compound that inhibits ?-glucosidase activity. Furthermore, molecular docking studies were performed to understand the binding interactions between the molecule and enzyme.

| S-EPMC6072357 | biostudies-literature

6-Phenyl-oxane-2,4-dione.

Project description:The title compound, C11H10O3, is a phenyl-subsituted dihydro-pyran-dione in which the heterocycle adopts a boat conformation with the phenyl substituent canted 72.14?(5)° relative to the mean plane of the heterocycle.

| S-EPMC3588319 | biostudies-literature

Quinazoline-2,4(1H,3H)-dione.

Project description:In the title compound, C(8)H(6)N(2)O(2), inter-molecular N-H?O hydrogen bonds involving the amine and carbonyl groups create centrosymmetric dimers between adjacent nearly coplanar mol-ecules. These dimers are further connected by weak N-H?O hydrogen bonds, forming a two-dimensional network. Mol-ecules are packed in the crystal structure with adjacent benzene and pyrimidine rings approximately coplanar; the centroid-centroid separation is 3.863?Å and the dihedral angle between the mean planes is 0.64°, indicating the presence of weak inter-molecular face-to-face ?-? stacking inter-actions.

| S-EPMC2960707 | 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