Showing papers on "Benzopyran published in 2013"

Pharmacological activities of chromene derivatives: an overview

Abstract: Chromene (Benzopyran) was one of the privileged scaffold which appears as an important structural component in various natural products and also possess useful photochemical properties. The derivatives of benzopyran moiety can be capable of interacting with a variety of cellular targets which leads to their wide ranging biological activities such as antitumor, antihepatotoxic, antioxidant, anti-inflammatory, diuretic, anticoagulant, antispasmolytic, estrogenic, antiviral, antifungal, antimicrobial, anti-helminthic, hypothermal, vasodilatory, anti-HIV, antitubercular, herbicidal, anticonvulsant and analgesic activity. The potency of these clinically useful pharmacophore in treatment of cancer and inflammation and other activities encouraged the development of some more potent and significant compounds. The SAR studies reported that the substitution in the chromene nucleus with the specific groups increases the ability of the molecule to prevent diseases. This review is summarized to know about the different pharmacological activities of chromene nucleus with the extended knowledge about its anticancer and anti-inflammatory activity.

Synthesis, structure, and estrogenic activity of 2- and 3-substituted 2,3-dihydro-4H-1-benzopyran-4-ones

Abstract: Molecules with potent estrogenic activity are ~270 A3 hydrophobic structures that encompass two hydroxyls among which is at least one phenol. However, compounds with only one phenol or devoid of such a ring have been shown to enhance ERα-mediated transcription at concentrations much larger than those measured with E2. In this context, we show here that benzopyrans sharing one hydroxyl/methoxyl and containing an additional benzylidenyl or a spirocyclohexyl motif are able to induce ERE-dependent transcription in breast carcinoma cells.

Method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis

Abstract: The invention discloses a method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis The method comprises the following steps of: carrying out catalytic condensation reaction on aromatic aldehyde, an active methylene compound and ketene dimethyl under normal pressure to obtain the benzopyran derivative by using the functional ion liquid based on choline chloride as the catalyst The method for preparing benzopyran derivative by choline chloride functional ion liquid catalysis is simple to operate, high in yield, good in reusability of catalytic reaction system, gentle in reaction condition and good in industrial prospect

New Synthetic Approaches to Naturally Occurring and Unnatural Pyranoflavones

Abstract: Total synthesis of biologically interesting natural and unnatural pyranoflavones has been accomplished starting from readily available 2,4-dihydroxyacetophenone or 2,4-dihydroxy-6-methoxyacetophenone in three steps, i.e., benzopyran formation, condensation, and cyclization reaction.

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octa-hydro-1'H-dispiro-[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione.

Abstract: In the title compound C38H32N4O3, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) A, respectively. In the crystal, non-classical C—H⋯O inter­actions link the mol­ecules, generating an C(9) chain along the b-axis direction.

Photo- and thermochromic spirans. 38*. New (1-alkyl-4,5-diphenyl)imidazolyl-substituted spirobenzopyrans

Abstract: 3-Diphenylimidazolyl-substituted 2-hydroxybenzaldehyde has been obtained by the formylation of 2-diphenylimidazolyl-substituted phenol. From the obtained compound, new photochromic spiroindolinebenzopyrans containing a 4,5-diphenylimidazole group at the position 8 of the benzopyran fragment were synthesized. The obtained compounds possess photochromic properties in solution.

Bis-(1H-2-benzopyran-1-one) derivatives: Synthesis and antimicrobial evaluation

Abstract: The aim of the present study was to synthesize isocoumarin heterocycles and to elucidate the potential role of these compounds as biological active agents. A new series of isocoumarin derivatives containing two six-membered lactone rings is reported. 3-Aroyl-substituted isocoumarins (3) obtained by condensing 2- carboxy benzaldehyde (1) with bromoacetophenone derivatives (2) was further reacted with different aromatic aldehydes (4) affording bis-(1H-2-benzopyran-1-one) derivatives (5). This short review compiles examples of most promising antibacterial, antifungal and analgesic bis-(1H-2-benzopyran-1-one) derivatives. The products were characterized on the basis of analytical and spectral (IR, 1HNMR, C13NMR, Mass) data. The biological activity study revealed that all compounds showed promising activities and bis-(1H-2-benzopyran-1-one) derivatives (5) were found to be more active than 3-aroyl-substituted isocoumarins (3).

Synthetic method of benzopyran chiral compound

Abstract: The invention discloses a synthetic method of a benzopyran chiral compound. The method comprises the following steps: a compound with the structural formula I and a compound with the structural formula II carry out the condensation reaction to generate a compound with the structural formula III, and the compound with the structural formula III is oxidized to obtain the benzopyran chiral compound; the chemical additive adopts a benzoic acid or a substituted benzoic acid compound; and the chiral catalyst is a diphenyl prolinol ester compound or dinaphthyl prolinol ester compound. The synthetic method has the advantages that under the mild condition, relatively cheap raw materials are used, the benzopyran chiral compound derivate is synthesized with high yield, and the derivate is high in optical purity, accessible in raw material, and beneficial for large-scale production and application.

Synthesis and Evaluation of Substituted 4,4a-Dihydro-3H,10H-pyrano[4,3-b][1]benzopyran-10-one as Antimicrobial Agent

Abstract: A series of pyrano[4,3-b][1]benzopyranones (7a–t) were synthesized through hetero-Diels-Alder reaction of substituted 3-formylchromones (5) with enol ethers (6), characterized by IR, 1H NMR, 13C NMR, and mass spectral techniques. All the compounds were evaluated for antimicrobial activity against various bacterial and fungal strains, found to possess significant inhibitory potential, particularly, compounds bearing electron withdrawing group -fluoro such as 7i and 7h. Compounds were also tested and displayed a significant inhibitory potential against methicillin-resistant Staphylococcus aureus (MRSA).

Highly efficient organic dyes containing a benzopyran ring as a π–bridge for DSSCs

Abstract: A series of novel organic dyes containing a benzopyran ring as a π–bridge have been designed and applied in dye-sensitized solar cells (DSSCs). This series of dyes show the excellent DSSCs' performance, due to their efficient light-to-photocurrent conversion in the region from 380 nm to 600 nm, with the highest IPCE values exceeding 90%. Through modification of the donor units, an efficiency as high as 7.5% has been achieved under standard light illumination (AM 1.5G, 100 mW cm−2) by the dye CC103.

Palladium-Catalyzed Synthesis of Trimethylsilyl Substituted Benzopyran Derivatives

Abstract: Palladium catalysis is an efficient way to obtain trimethylsilyl substituted benzopyran derivatives. After screen- ing a series of reactions , we found optimized conditions.

Synthesis of Benzopyran Linked Pyrrolo[2,1-c][1,4]benzodiazepines as DNA-Binding and Potential Anticancer Agents

Abstract: A series of twelve benzopyran linked pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) have been synthesized. They exhibit significant DNA-binding activity and excellent cytotoxic activity against various human cancer cell lines.

New simple method for synthesizing 4H-benzopyran ring heterocyclic compound

Abstract: The invention relates to a new simple method for synthesizing a 4H-benzopyran ring heterocyclic compound. The 4H-benzopyran ring heterocyclic compound is prepared by the following steps of: taking salicylic aldehyde or a salicylic aldehyde derivative as a raw material; by utilizing the nucleophilicity of a phenolic hydroxyl group and the electrophilicity of an aldehyde group in the raw material, performing intermolecular cyclization reaction with a beta-dicarbonyl type compound or a carbonyl type compound with an electron withdrawing group in the beta-position in the presence of Lewis acid; and further constructing the heterocyclic compound with a 4H-benzopyran ring mother nucleus through one step. The method has the advantages of simple reaction, high yield, capability of realizing fast synthesis of a large number of various substituted 4H-benzopyran ring heterocyclic compound libraries, and capability of accelerating the discovery of lead compounds of medicaments. In the formula 1, R1, R2, R3, R4, R5 and R6 are respectively and independently selected from one of hydrogen, C1-C6 alkyl, C5-C10 aromatic ring or C5-10 aromatic ring-substituted C1-C6 alkyl, and at least two are different.

GREEN ONE-POT SYNTHESES of 1H- AND 4H-CHROMENES DERIVATIVES USING SiO2-Pr-SO3H AS CATALYST

Abstract: The chromene or benzopyran substructure is frequently found in naturally occurring heterocycles that exhibit biological activity such as spasmolytic, diuretic, anticoagulant, anticancer and anti anaphylactic activity. They can be used for the treatment of neurodegenerative diseases, including Alzheimer’s disease, amyotrophic lateral sclerosis, Huntington’s disease, Parkinson’s disease, AIDS connected dementia and Down’s syndrome, and then treatment of schizophrenia and myoclonus. A few methods for the synthesis of chromene derivatives have been reported in literature such as employing aluminum oxide, H14[NaP5W30O110], methan sulfonic acid and ammonium cerium (IV) nitrate as catalyst. In recent years, much attention was afforded to the heterogeneous catalysts due to economic and environmental considerations. These acid

Synhtesis, Characterization and Cytotoxic Activity of Analogues of 3- Methyl Flavone

Abstract: The flavonoids are polyphenolic compounds and universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chroman (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C 6 -C 3 -C 6 ), composed of a chroman (C 6 -C 3 ) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B), substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. Various analogues of 3-methylflavones were synthesised, purified and characterised by UV, IR,1HNMR and mass spectrometry. All the synthesised compounds were evaluated for their cytotoxic activityby MTT assay against HeLa cell line. Most of the compounds show moderate activity,whereas thecompounds like FA-04, FA-20, FA-10 and FA-13 have shown good activity having IC 50 value 22.00, 25.49.26.24 and 26.35 µg/ ml respectively, in comparison to standard molecule Cisplastin had IC 50 value 6- 12.5µg/ml. Thus it appears the presence of 3-methyl group in the flavone nucleus significantly influences the log ‘P’ value of all the twenty test compounds. The prominent activity the of above compounds is probably because of 3-methyl and N, N-dimethyl amino substitution on 4 ’ -positionof flavonoid nucleus.

Cyclotrimerization of Unsymmetrically Bromo-Substituted Diynes: Toward the Synthesis of Potential Selective Inhibitors of Tyrosine Kinase 2.

Abstract: The process is examined in the presence of Rh- and Ru-catalysts concerning the formation of benzopyran and benzofuran derivatives.

Schiff base compound containing benzopyran, preparation method and use thereof

Abstract: The invention discloses a Schiff base compound containing benzopyran having a structure as shown in formula I, and a pharmaceutically acceptable salt thereof, wherein R represents one of hydrogen and C1-C4 alkyls; X represents S or SO2; R1 represents H, halogen, alkyl of C1-C4 or alkoxy; and R2 represents H, halogen, alkyl of C1-C4 or alkoxy. The invention also discloses a preparation method of the compound, and simultaneously, a pharmaceutical composition with the compound or the pharmaceutically acceptable salt thereof as an active effective constituent, as well as an application thereof as an antitumor drug, especially application in the aspect of preparing drugs for treating breast cancer, lung cancer and stomach cancer.

3- (1' -adamantyl) - 1 - aminomethyl - 3, 4 - dihydro - 5, 6 - dihydroxy - 1h - 2 - benzopyran for use in the treatment of a disease associated with beta-amyloid induced toxicity

Abstract: The present invention relates to the new use of the compound 3-(1′-adamantyl)-1-aminomethyl-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyran for the treatment of diseases or conditions that are associated with β-amyloid induced toxicity, such as Alzheimer's disease.

8,8-Dimethyl-8,9-dihydro-7H-chromeno[2,3-b]quinoline-10,12-dione.

Abstract: In the title compound, C18H15NO3, the fused benzopyran and pyridine rings are essentially coplanar [r.m.s. deviation = 0.0533 A with a maximum deviation of 0.080 (1) A for a benzene C atom]. The cyclo­hexa­none ring adopts an envelope conformation with the dimethyl-substituted C atom 0.660 (2) A out of the plane formed by the remaining ring atoms (r.m.s. deviation = 0.0305 A). The dihedral angle between the mean planes of the pyran and cyclo­hexa­none rings is 12.95 (6)°. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, leading to chains running along [011].

(6′R*,7′R*)-7′-(1,3,-Diphenyl-1H-pyrazol-4-yl)-1,2,5′,6′,7′,7a',3′′,4′′-octa­hydro-1′H,2′′H-dispiro­[acenaphthyl­ene-1,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,3′′-[1]benzopyran]-2,4′′-dione

Abstract: In the title compound, C40H29N3O3S, the pyran ring adopts a sofa conformation, the thia­zolidine ring adopts a twisted conformation and the pyrrolidine ring adopts an envelope conformation with the N atom as the flap. The pyrazole ring is essentially planar [maximum deviation = 0.002 (2) A] and forms dihedral angles of 4.8 (1) and 39.0 (1)°, respectively, with the benzene rings attached to the N and C atoms. The acenapthylene ring system is approximately planar [maximum deviation = 0.058 (2) A] and forms dihedral angles of 85.9 (1) and 48.5 (1)°, respectively, with the pyrollothia­zole and chromene ring systems. The mol­ecular conformation is stabilized by three weak intra­molecular C—H⋯O hydrogen bonds, which generate one S(8) and two S(6) ring motifs. In the crystal, pairs of C—H⋯O hydrogen bonds link centrosymmetrically related mol­ecules into dimers, generating R22(14) ring motifs. The crystal packing also features pairs of C—H⋯π inter­actions, which link the dimers into a supra­molecular chain along the b axis.

Benzopyran derivative, its preparation method and application

Abstract: The invention provides a benzopyran derivative and a preparation method of the benzopyran derivative Under sunlight or ultraviolet irradiation, the benzopyran derivative provided in the invention can change from colorless to yellow or orange red, thus being a compound with excellent photochromic performance Also, relative to naphthopyran derivatives, the benzopyran derivative involved in the invention has a simple synthesis method and low-cost raw materials, thus being suitable for large-scale industrial production The invention also provides application of the benzopyran derivative

New simple method for synthesizing 2H-benzopyrano (2, 3-b) 2H-benzopyran ring heterocyclic compound

Abstract: The invention relates to a new simple method for synthesizing a 2H-benzopyrano (2, 3-b) 2H-benzopyran ring heterocyclic compound. The 2H-benzopyrano (2, 3-b) 2H-benzopyran ring heterocyclic compound is prepared by the following steps of: taking salicylic aldehyde or a salicylic aldehyde derivative as a raw material; by utilizing the nucleophilicity of a phenolic hydroxyl group and the electrophilicity of an aldehyde group in the raw material, performing intermolecular cyclization reaction with a beta-carbonyl type compound or a carbonyl type compound with an electron withdrawing group in the beta-position in the presence of Lewis acid; and further constructing the heterocyclic compound with a 4H-benzopyran ring mother nucleus through one step. The method has the advantages of simple reaction, high yield, capability of realizing fast synthesis of a large number of various substituted 2H-benzopyrano (2, 3-b) 2H-benzopyran ring heterocyclic compound libraries, and capability of accelerating the discovery of lead compounds of medicaments. In the formula 1, R1, R2, R3, R4, R5 and R6 are respectively and independently selected from one of hydrogen, C1-C6 alkyl, C5-C10 aromatic ring or C5-10 aromatic ring-substituted C1-C6 alkyl, and at least two are different.