Showing papers on "Benzopyran published in 2018"
TL;DR: The combined approach of ligand-based and structure-based models provided an improved understanding in the interaction between benzopyran chemical class and COX-2 inhibition, which will guide the future identification of more potent anti-inflammatory drugs.
Abstract: The Gaussian-based 3D-QSAR studies for 58 selective COX-2 (cyclooxygenase-2) inhibitors belonging to benzopyran chemical class were performed. Partial least squares analysis produced statistically significant model with (R
training
2
= 0.866) and predictability (Q
training
2
= 0.66, Q
test
2
= 0.846). The 3D-QSAR model includes steric, electrostatic, hydrophobic, and hydrogen bond acceptor field indicators, whereas the potential field contributions indicate that the steric and hydrophobic features of the molecules play an important role in governing their biological activity. A molecular docking simulation and protein–ligand interaction pattern analysis reveal the importance of Tyr-361 and Ser-516 of the COX-2 active site for X-ray crystal structures and this class of molecules. Thus the combined approach of ligand-based and structure-based models provided an improved understanding in the interaction between benzopyran chemical class and COX-2 inhibition, which will guide the future identification of more potent anti-inflammatory drugs.
20 citations
TL;DR: In this paper, the authors focus on important benzopyran analogs with anti-breast cancer activity and highlight their mechanisms of action and propose a systematic review of these analogs.
Abstract: One of the naturally occurring compounds containing oxygen moiety is benzopyran. Depending on its substitution pattern, different biological effects are shown. The benzopyran ring system is present in many natural products (such as genistein, hesperidin, and warfarin) as well as synthetic products. It displays pharmacological properties such as antitumor, anti-HIV, antimicrobials, anti-inflammatory, and anticoagulants. The sufficient literature support and the fact that benzopyran has potential as a pharmacophore particularly as anti-breast cancer, etc, current research seemed pertinent keeping in view the mechanism of anti-breast cancer activity. Therefore, the objective of this review is to focus on important benzopyran analogs with anti-breast cancer activity and highlight their mechanisms of action.
10 citations
TL;DR: A microwave assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described in this paper.
Abstract: A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.
7 citations
TL;DR: In this article, spirobenzopyranindolines containing a rhodamine fragment linked to a benzopyrant fragment with an aminomethylene spacer were synthesized by the reaction of 7-hydroxy-6-formyl-substituted spiropyrans and rhodamines B hydrazide.
Abstract: Novel spirobenzopyranindolines containing a rhodamine fragment linked to a benzopyran fragment with an aminomethylene spacer were synthesized by the reaction of 7-hydroxy-6-formyl-substituted spiropyrans and rhodamine B hydrazide. The synthesized spiropyrans in toluene and acetone are present in the spiropyran‒spirolactam form. The 5-methyl-substituted was the only to exhibit photochromism. Adding Zn(II), Ni(II), Co(II), and Cd(II) perchlorates to the spiropyran solutions leads to intense coloration due to complex formation.
5 citations
TL;DR: In this paper, the radical cyclization reactions of cyclic 1,3-dicarbonyl compounds and α,β-unsaturated alcohols through Mn(OAc)3 were performed.
3 citations
Patent•
29 Jun 2018
TL;DR: In this paper, a 2-aryl benzopyran dihydrothiophene derivative with antibacterial activity was described and a synthesis method and application of it was presented, where R1 and R2 are independently selected from hydrogen, fluorine, chlorine, bromine, methoxy, methyl or nitro.
Abstract: The invention discloses a 2-aryl benzopyran dihydrothiophene derivative with antibacterial activity as well as a synthesis method and application thereof. The structure of the 2-aryl benzopyran dihydrothiophene derivative is shown as formula (I), wherein R1 and R2 are independently selected from hydrogen, fluorine, chlorine, bromine, methoxy, methyl or nitro. The 2-aryl benzopyran dihydrothiophenederivative has better antibacterial effects and can be used as a potential antibacterial agent. The formula (I) is shown in the description.
2 citations
TL;DR: All three Benzopyran-2-one derivatives possess anxiolytic activity, SMA, skeletal muscle relaxation and anti-convulsant activity but do not possess analgesic activity.
Abstract: Background: Present study was carried out to evaluate neuroprotective activity of newly synthesized Benzopyran-2-one derivatives. Methods: Three compounds namely 7-(2-(o-furan)-phenyl thiazolidinyl)-4-methyl benzopyran-2-one (FPTMB), 7-(2-(N,N dimethyl)-phenyl thiazolidinyl)-4-methyl-benzopyran-2-one (DPTMB) and 7-(2-(p-hydroxy)phenyl thiazolidinyl)-4-methyl-benzopyran-2-one (HPTMB) were assessed for their effects on Central Nervous System (CNS) using a series of established pharmacological tests including evasion test for anxiolytic activity, actophotometer test for spontaneous motor activity (SMA), rotarod test for skeletal muscle relaxation and pentylenetetrazole (PTZ) induced convulsant model for anti-convulsant activity followed by Eddy’s hot plate and Haffner’s tail clip method for analgesic activity. Results: These derivatives were found to produce symptoms of CNS depression in conscious mice, viz. significant reduction in SMA and exploratory behavior by evasion test and skeletal muscle relaxation and showed a significant prolongation of latency and reduced duration of convulsions induced by PTZ. Further, these test compounds failed to show a significant anti-nociceptive activity evaluated by centrally acting analgesic models i.e., Eddy’s hot plate and Haffner’s tail clip methods. Conclusion: It may be concluded that all three derivatives possess anxiolytic activity, SMA, skeletal muscle relaxation and anti-convulsant activity but do not possess analgesic activity.
1 citations
1 citations
Patent•
09 Nov 2018
TL;DR: In this paper, a 4-(2H-benzopyran-3-yl)-2-vinyl thiazole compound capable of inhibiting PIM1 kinase activity, and application thereof, was revealed.
Abstract: The invention belongs to the technical field of medicines, and discloses a 4-(2H-benzopyran-3-yl)-2-vinyl thiazole compound capable of inhibiting PIM1 kinase activity, and application thereof. The compound has a structure as shown in the general formula (I), wherein R1 represents naphthenic base, phenyl group or substituted phenyl of C4 to C7; R2 represents alkyl group, hydroxy, hydroxyalkyl, halogen, halogen alkyl and cyanogroup of C1 to C10. The compound can be used for preparing a PIM1 kinase inhibitor, so that more options are provided for preparing a targeting antineoplastic drug. The formula is shown in the description.
1 citations
Patent•
24 Apr 2018
TL;DR: In this article, the authors presented a preparation method for catalytically synthesizing 2,3-di-substituted-4H-benzopyran by Sc(III).
Abstract: The invention provides a preparation method for catalytically synthesizing 2,3-di-substituted-4H-benzopyran by Sc(III). A 2-(hydroxyl (phenyl) methyl) phenols compound and a diphenyl acetylene compound are subjected to [4+2] cycloaddition reaction through Sc (III) catalysis by a one-step method to generate a series of 2,3-di-substituted-4H-benzopyran compounds, and the yield is 83%-95%. The methodis simple to operate, raw materials and reagents are simple, reaction products are high, the shortcomings that by a traditional method, a catalyst is expensive and conditions are harsh are avoided, products are easily separated and purified, and the preparation method is suitable for synthesis of various 2,3-di-substituted-4H-benzopyrans compounds.
1 citations
Patent•
03 Apr 2018
TL;DR: In this article, a preparation technology of 7-hydroxyl-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid is presented.
Abstract: The invention provides a preparation technology of 7-hydroxyl-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid and belongs to the technical field of medicine synthesis. The 7-hydroxyl-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid serves as a key intermediate of a renal failure resisting drug, namely, nicousamide, 2-hydroxyl-4-methoxy-3-methylbenzaldehyde is taken as an initial material, in step 1, 2-hydroxyl-4-methoxy-3-methylbenzaldehyde is obtained after demethylation, in step 2, 2-hydroxyl-4-methoxy-3-methyl-5-nitrobenzaldehyde is obtained through a nitration reaction, in step 3, 2-hydroxyl-4-methoxy-3-methyl-5-nitrobenzaldehyde is condensed with diethyl malonate and 7-methoxy-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid is obtained, and in step 4, 7-hydroxyl-8-methyl-6-nitro-2-oxo-2H-benzopyran-3-carboxylic acid is obtained after demethylation.
Patent•
24 May 2018
TL;DR: In this article, a method for purifying (2R, 3R, 4S)-6-amino-4-[N-(4-chlorophenyl)-N-(1H-imidazol-2-ylmethyl)amino]-3-hydroxy 2-methyl 2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran was presented.
Abstract: The present invention provides a method for purifying (2R,3R,4S)-6-amino-4-[N-(4-chlorophenyl)-N-(1H-imidazol-2-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran, comprising converting amorphous (2R,3R,4S)-6-amino-4-[N-(4-chlorophenyl)-N-(1H-imidazol-2-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran into a crystal form thereof. In addition, the present invention provides: a novel crystal form of the (2R,3R,4S)-6-amino-4-[N-(4-chlorophenyl)-N-(1H-imidazol-2-ylmethyl)amino]-3-hydroxy-2-methyl-2-dimethoxymethyl-3,4-dihydro-2H-1-benzopyran; and a preparation method therefor.
Patent•
25 Dec 2018
TL;DR: In this paper, a fluorescent probe based on a benzopyran nitrile derivative and a preparation method and application of the fluorescent probe is described, which can selectively act on a cyanogen under physiological conditions, a solution becomes green from faint yellow, while near infrared fluorescence is remarkably enhanced.
Abstract: The invention provides a fluorescent probe based on a benzopyran nitrile derivative and a preparation method and application of the fluorescent probe. The chemical structural formula of the fluorescent probe is as shown in specification. The benzopyran nitrile derivative can selectively act on a cyanogen under physiological conditions, a solution becomes green from faint yellow, meanwhile, near infrared fluorescence is remarkably enhanced, and particularly, the fluorescent probe conveniently detects the cyanogen in cells.
Patent•
10 Aug 2018
TL;DR: In this paper, a preparation method of 2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)ethanone is presented.
Abstract: The invention provides a preparation method of 2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)ethanone shown as a formula (I). The preparation method comprises the following steps: step (a), preparing an organic zinc reagent (III): enabling zinc powder and a compound shown as a formula (IV) to react in an anhydrous solvent A for 2 to 3h at 50 to 70 DEG C, so as to generate the organic zincreagent (III), wherein in the formula (III) or (IV), X1 is selected from Cl, Br and I and X2 is Cl; step (b), enabling the organic zinc reagent which does not need to be post-treated, and 6-fluoro-2-cyano-3,4-dihydro-2H-1-benzopyran shown as a formula (II) to react in an anhydrous solvent B for 15 to 48h at 0 to 45 DEG C; then quenching the unreacted organic zinc reagent and treating an obtained reaction solution to obtain the 2-chloro-1-(6-fluoro-3,4-dihydro-2H-1-benzopyran-2-yl)ethanone shown as the formula (I). The method provided by the invention has the advantages of simple technology, moderate reaction conditions and high safety and is suitable for industrial production. The formula of step (b) is shown in the description.