Showing papers on "Benzopyran published in 2022"
TL;DR: In this paper, an environmentally friendly synthesis of two heterocyclic α,β-unsaturated carbonyl group benzopyran compounds (4]-(2E)-3-(1H-indol-3-yl)prop-2-enoyl]-2H-1-benzopyrin-2.
19 citations
TL;DR: In this article , an environmentally friendly synthesis of two heterocyclic α,β-unsaturated carbonyl group benzopyran compounds (4]-(2E)-3-(1H-indol-3-yl)prop‑2-enoyl]-2H-1-benzopyrans-2-one, and 4-(6-( 1H-3)-indolyl)-2,3-dihydropyrimidin-2(1H)thione-4-yl)-2-benzmanone) referred to as Ch-I and Ch-II and explores their corrosion inhibition against API steel type in 15% hydrochloric solution.
18 citations
TL;DR: In this article , photochromic spiropyrans (SPPs) with fluorine substituents and cationic fragments or formyl groups at positions 6′ and 8′ of the 2H-chromene moiety were synthesized using a simple one-pot method.
11 citations
TL;DR: In this paper , 2-Amino-6,6-diméthyl-5-oxo-4-(4-méthoxyphenyl)-5,6,7,8-tetrahydro-4H-benzopyran-3-carbonitrile (HL1) and (HL2) have been prepared in good yield using Ni(NO3)2) as catalyst via cyclocondensation in a single step.
2 citations
TL;DR: In vivo studies in BALB/c mice inferred that compound 47 stimulates bone anabolism as evident from histological and gene expression studies at 5 mg, and structural activity relationship (SAR) and pharmacokinetic studies suggest compound 47 as a BMP2 upregulator and a potential bone anabolic lead for combating future bone metabolic disorders.
Abstract: In search of novel osteogenic entities, a series of twenty-seven quinazolinone-benzopyran-indole hybrids were designed and synthesized using molecular hybridization approach. All the compounds were scrutinized for their osteogenic potential, primarily based on alkaline phosphatase assay as one of the major anabolic markers. From the primary screening, four osteogenic compounds were sorted from the series and were found nontoxic to the osteoblasts. Further, increased osteoblast differentiation and osteogenic mRNA upregulations suggest compound 47 as the most potent osteoanabolic agent. Immunoblot and ELISA analysis demonstrated that compound 47 promotes osteogenesis via RUNX2 and BMP2 mediated non-canonical p38 pathway. In vivo studies in BALB/c mice inferred that compound 47 stimulates bone anabolism as evident from histological and gene expression studies at 5 mg. kg-1. day-1 dose. Furthermore, structural activity relationship (SAR) and pharmacokinetic studies suggest compound 47 as a BMP2 upregulator and a potential bone anabolic lead for combating future bone metabolic disorders.
2 citations
TL;DR: RhQ has a higher antitumor efficacy than RhS, and RhQ demonstrated significantly lower toxicity in vivo than CDDP, making it a promising Rh(III)-based anticancer therapeutic and fluorescence imaging agent.
Abstract: Four novel rhodium(III) complexes, [RhIII(QB1)Cl3(DMSO)] (RhN1), [RhIII(QB2)Cl3(CH3OH)]·CH3OH (RhN2), [RhIII(QB3)Cl3(CH3OH)]·CH3OH (RhS), and [RhIII(QB4)Cl3(DMSO)] (RhQ), bearing quinoline-benzopyran ligands (QB1-QB4) were synthesized and used to develop highly anticancer therapeutic and fluorescence imaging agents. Compared with the QB1-QB4 ligands (IC50 > 89.2 ± 1.7 μM for A549/DDP), RhN1, RhN2, RhS and RhQ exhibit selective cytotoxicity against lung carcinoma cisplatin-resistant A549/DDP (A549CDDP) cancer cells, with IC50 values in the range of 0.08-2.7 μM. The fluorescent imaging agent RhQ with the more extended planar QB4 ligand exhibited high anticancer activity in A549CDDP cells and was found in the cell nucleus fraction, whereas RhS had no fluorescence properties. RhQ and RhS may trigger cell apoptosis by causing DNA damage and initiating the mitochondrial dysfunction pathway. Furthermore, RhQ has a higher antitumor efficacy (ca. 55.3%) than RhS (46.4%) and cisplatin (CDDP, 33.1%), and RhQ demonstrated significantly lower toxicity in vivo than CDDP, making it a promising Rh(III)-based anticancer therapeutic and fluorescence imaging agent.
2 citations
TL;DR: The results of biochemical studies using a palmitic acid (PA) induced insulin resistance (IR) model show that (+)-ganodercin S, cochlearol F, (+)- and (-)-ganodercins V reduce the expression of collagen I as discussed by the authors .
1 citations
TL;DR: In this article , a series of new benzopyran derivatives was synthesized and characterized by spectroscopic means (1 H NMR, 13 C NMR and HRMS) and were assessed for their inhibitory potential on the α-amylase enzyme.
1 citations
1 citations
TL;DR: In this article , two 2 H -1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2 H-1-Benzopryn-5-carboxylate (1 ) and methyl 8hydroxy -2, 2,2 -dimethyl -2 H 1-benzinopryran-6 carboxylates (2 ), including a new compound (1) were isolated from the twigs of Chaenomeles sinensis and characterized based on analysis of NMR data.
Abstract: Two 2 H -1-benzopyran derivatives, methyl 8-hydroxy-2,2-dimethyl-2 H -1-benzopyran-5-carboxylate ( 1 ) and methyl 8-hydroxy-2,2-dimethyl-2 H -1-benzopyran-6-carboxylate ( 2 ), including a new compound ( 1 ) were isolated from the twigs of Chaenomeles sinensis . Their chemical structures were characterized based on analysis of NMR data including 1 H and 13 C, COSY, HSQC, and HMBC and HRMS data. The isolated compounds ( 1 and 2 ) were assessed for their anti-neuroinflammatory activity by measuring inhibition levels of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated BV-2 cells and for their neurotrophic activity by the secretion of nerve growth factor (NGF) in C6 cells. Compounds 1 and 2 exhibited powerful anti-neuroinflammatory effects with IC 50 values of 17.14 and 19.30 μ M, respectively, without cell toxicity, and also showed moderate effects on the stimulation of NGF secretion levels with 113.15 ± 3.54 and 130.20 ± 8.03%, respectively. The biosynthetic pathway of 1 and 2 was proposed that they would be derived from a protocatechuic acid and an isoprenyl unit.
TL;DR: In this paper , C19H18O2 has been synthesized using the Claisen-Schmidt condensation reaction from the mixture of 2,3 dihydro-4H-1-benzopyran-4-one and 2, 3,4-trimethoxyphenyl methylidene in the presence of ethanol as solvent.
18 Apr 2022
TL;DR: In this article , a 3D-QSAR model was used to develop 17 new compounds against breast cancer and 23 new compounds for lung cancer using a computationally driven approach in building and finding novel coumarin scaffolds for cancer inhibition.
Abstract: Abstract With the rising number of cancer patients and the associated cancer resistance pathway, the demand for design of innovative novel drugs has never been greater. Coumarins (2H-1-benzopyran-2-one) are an antibiotic that is effective against a variety of diseases. Breast cancer and lung cancer were the focus of this research. To create a pharmacophore hypothesis, biologically active coumarin derivatives were tested against MCF-7, a breast cancer cell line, and A-549, a lung cancer cell line, using IC50 values. The AAARR 1 theory had the highest score. Both types of cancer were studied using a 3D QSAR model. To determine R 2 and Q 2 values; the pIC50 of the intended compound were used to generate the 3D-QSAR model which showed excellent predictive and descriptive capacity. The QSAR approach was used to develop 17 new compounds against breast cancer and 23 new compounds for lung cancer. VEGFR-2 (PDB ID: 4ASD) breast cancer protein and Protein kinase C iota (PKCι) lung cancer causing proteins were used to dock with newly designed compounds. The docking data were compared to FDA-approved breast cancer medications Abemaciclib and lung cancer treatments Vinorelbine. Molecular dynamic simulation was used to verify the docking results. The protein's stability was demonstrated using the designed ligand. The research presents a computationally-driven approach in building and finding novel coumarin scaffolds for cancer inhibition.
TL;DR: In this paper, the binding interaction with protein PDBs: 1HNY and PDB:5NN3 through molecular docking by autodockpyrx was investigated.
Abstract: Alpha amylase and alpha-glucosidase inhibitors play a key role in treating diabetes mellitus. Based on this idea the present study aimed in designing different benzopyran analogs and investigate the binding interaction with protein PDB: 1HNY and PDB:5NN3 through molecular docking by autodockpyrx. The results evaluated by docking studies found that different substituted derivatives of 4-Hydroxycoumarine, 3-acetyl 4-hydroxy coumarin, 8 hydroxycoumarine, 7-hydroxycoumarine, 4-hydroxy, 5-methoxycoumarine compounds and compared with standard quercetin which is the target protein. The compound showing the best score for 1HNY is hydroxyl substituent with dicyandiamide,4-methyl carbothioamide, 3-methoxy formamide, 3-methoxycarbothioamide and for 5NN3 is 4- methyl formamide,4-Fluro carbohioamide. Totally 107 compounds were subjected to docking and the selected fifteen potent compounds were subjected to predict the molecular property, drug-likeness, absorption, distribution, and metabolism analysis by using online free software Molinspiration and Swiss ADME, which were satisfied with the Lipinski rule of 5 which plays an important role in filtering the protocol. The filtered compounds showed 0 violations for the physiochemical properties of the molecule
TL;DR: In this article , a series of pyridinium-based ionic liquids (PBILs) were synthesized through a simple method, which was initially evaluated as catalysts for the synthesis of tetrahydro[b]benzopyran derivatives via a one-pot three-component reaction involving aldehydes, malononitrile, and dimedone.
Abstract:
In this work, a series of pyridinium-based ionic liquids (PBILs) were synthesized.
Pyridinium-based ionic liquids (PBILs) were synthesized through a simple method, which was initially evaluated as catalysts for the synthesis of tetrahydro[b]benzopyran derivatives via a one-pot three-component reaction involving aldehydes, malononitrile, and dimedone.
The PBILs perform well in this condensation reaction, especially 1-methylpyridin-1-ium dimethyl phosphate (MPDMP).
The advantages of this procedure are good yields, short reaction time, simplicity of implementation, and inexpensive starting materials.
TL;DR: In this paper , the 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions.
Abstract: The 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions. The reaction using potassium carbonate and 18-crown-6 in THF was the best condition, giving 1H-2-benzopyran-5,8-dione derivatives in good yields. The UV-vis absorption spectrum and cyclic voltammogram of the synthesized 1H-2-benzopyran-5,8-dione derivative were measured, clarifying the photophysical and redox properties. 1H-2-Benzopyran-5,8-dione skeleton was found to be selectively synthesized through a cascade reaction of Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters. The photophysical and redox properties of the synthesized 1H-2-benzopyran-5,8-dione with red color were also elucidated.
TL;DR: The synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one is reported using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions.
Abstract: Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions. This compound was afforded in 80% yield.
TL;DR: In this paper , the authors correct the article DOI: 10.3389/fphar.2022.945323 and 10.3489/FphAR.
Abstract: [This corrects the article DOI: 10.3389/fphar.2022.945323.].
TL;DR: In this paper , the authors synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative) in 62% yield.
Abstract: With the aim of obtaining derivatives belonging to 2′,3′-diphenyl-3H-spiro[[2]benzofuran-1,4′-imidazole]-3,5′(3′H)-dione nucleus, we synthesized 4-[(3-amino-1-oxo-1H-2-benzopyran-4-yl)amino]benzoic acid (a 3,4-diaminoisocoumarine derivative), a known precursor of 4-[(1-carbamoyl-3-oxo-1,3-dihydro-2-benzofuran-1-yl)amino]benzoic acid (a phthalide–carboxamide-bearing system) by a novel methodology that we report here. The reaction conditions were optimized to afford the latter in 62% yield.