Showing papers on "Benzopyran published in 2017"

Asymmetric Organocatalytic Synthesis of Benzopyran‐ and Benzofuran‐Fused Polycyclic Acetals

Abstract: An efficient organocatalytic method for the asymmetric preparation of benzopyran- and benzofuran-fused polycyclic acetals is described for the first time. This useful approach includes an interesting tunable Michael–acetalization of nitrostyrenes or α-aromatization–acetalization of quinones. Under mild conditions, simple cyclic hemiacetals could be stereoselectively converted into four different types of polyheterocycles that serve as scaffolds for a number of bioactive natural products.

Novel benzopyran derivatives and their therapeutic applications: a patent review (2009-2016).

Abstract: Introduction: The benzopyran derivatives present a wide variety of biological activity and behaviour. At the same time the benzopyran derivatives support their use as therapeutic agents for multiple diseases. Their structural characteristics correlated to physicochemical properties seem to define the extent of the biological activity.Areas covered: This review summarizes new patents published on new benzopyran derivatives from 2009 to 2016.Expert opinion: Many benzopyran derivatives have vivo/vitro biological responses. Their clinical evaluation will be critical to assess therapeutic utility. The compounds containing benzopyran moiety is well defined as lead compounds for design of new more promising molecules.

Design and synthesis of benzopyran-based inhibitors of the hypoxia-inducible factor-1 pathway with improved water solubility.

Abstract: While progress has been made in treating cancer, cytotoxic chemotherapeutic agents are still the most widely used drugs and are associated with severe side-effects. Drugs that target unique molecular signalling pathways are needed for treating cancer with low or no intrinsic toxicity to normal cells. Our goal is to target hypoxic tumours and specifically the hypoxia inducible factor (HIF) pathway for the development of new cancer therapies. To this end, we have previously developed benzopyran-based HIF-1 inhibitors such as arylsulfonamide KCN1. However, KCN1 and its earlier analogs have poor water solubility, which hamper their applications. Herein, we describe a series of KCN1 analogs that incorporate a morpholine moiety at various positions. We found that replacing the benzopyran group of KCN1 with a phenyl group with a morpholinomethyl moiety at the para positions had minimal effect on potency and improved the water solubility of two new compounds by more than 10-fold compared to KCN1, the lead compound.

Efficient synthesis and biological evaluation of new benzopyran-annulated pyrano[2,3-c]pyrazole derivatives.

Abstract: A one-pot method has been described to synthesize benzopyran-annulated pyrano[2,3-c]pyrazoles, effectively by combining O-alkenyloxy/alkynyloxy-acetophenones with various pyrazolones in triethylammonium acetate (TEAA) under microwave irradiation. While combination of O-allyloxy- or O-prenyloxy-acetophenones with pyrazolones occurred efficiently, that of O-propargyloxy-acetophenones was found effective in the presence of ZnO catalyst, via a domino Knoevenagel–hetero-Diels–Alder (DKHDA) reaction. Aminobenzopyran frameworks were also synthesized, after nitro-containing products were reduced in tandem with iron(II) in an acidic medium. The in vitro antiproliferative activity of these compounds was measured and discussed against gram-positive, gram-negative and M. tuberculosis bacteria, fungi, and various representative human solid tumor cell lines, in addition to their ferric reducing antioxidant capability.

Pteleifolols A–E, acetophenone di- C -glycosides and a benzopyran dimer from the leaves of Melicope pteleifolia

Abstract: Four new acetophenone di-C-glycosides, pteleifolols A–D (1–4) and a new dimeric benzopyran, pteleifolol E (5), were isolated from the leaves of Melicope pteleifolia. Seven known compounds, including 2,4,6-trihydroxyacetophenone-3,5-di-C-glucopyranoside (6), were also isolated. Structures of the new compounds (1–5) were established by using spectroscopic and spectrometric techniques, including 1D and 2D nuclear magnetic resonance (NMR), UV, and high-resolution electrospray ionization mass spectrometry (HR-ESI–MS) data. Pteleifolols A–D (1–4) were E-p-coumaroyl, Z-p-coumaroyl, E-feruloyl, and benzoyl esters of 6, respectively. Pteleifolol E (5) was a dichromene dimerized through a C2 unit.

Benzopyran nitrile-based sulfite fluorescence probe and preparation method thereof

Abstract: The invention belongs to the technical field of anion detection and relates to a benzopyran nitrile-based sulfite fluorescence probe and a preparation method thereof. The preparation method comprises the following steps: reacting 2-methylbenzopyran malononitrile and p-hydroxy benzaldehyde to produce 2-(1-hydroxyvinyl phenyl) benzopyran malononitrile, and reacting with acetylpropionic acid to prepare the product. After sulfite ions are added, fluorescence appears at 710nm, the fluorescence peak is enhanced along with increase of the concentration of the sulfite ions, the fluorescence intensity presents a linear relation with the sulfite ion concentration in a range (0-8)*10 M of the concentration of the sulfite ions. The solution color is changed from yellow to blue so as to achieve a colorimetric detection effect. The probe molecule has the characteristic of high interference resistance in a coexistence system of the sulfite ions and other multiple negative ions, and the fluorescence probe is high in selectivity, high in sensitivity and fast in response and can be well applied to sulfite detection in the environment.

Trapping of Hexadehydro-Diels–Alder Benzynes with Exocyclic, Conjugated Enals as a Route to Fused Spirocyclic Benzopyran Motifs

Abstract: Exocyclic, conjugated enals react with benzynes generated by heating various triyne-containing substrates to produce spirocyclic benzopyran derivatives. These products are consistent with a mechanistic sequence that involves initial net [2+2] cycloaddition of the benzyne and aldehyde followed by 4π-electrocyclic ring opening and 6π ring closing.

Modified Coumarins. 40. Synthesis of Benzopyran-2-One Carbonyl Derivatives of 9-Nitrocytisine

Abstract: Derivatives of coumarins, furocoumarins, and dihydropyranocoumarins containing a 9-nitrocytisine moiety were synthesized

An Efficient and Concise Synthesis of N-3-Substituted 9-Methoxy-4H-[1]-benzopyrano[2,3-d]pyrimidine-4(5H)-imines and Form­amidine Derivatives from Methyl N-(3-Cyano-8-methoxy-4H-[1]-benzopyran-2-yl)methanimidate

Abstract: A four-step microwave-assisted reaction of N-3-susbstituted 4H-[1]-benzopyrano[2,3-d]pyrimidine-4(5H)-imines and formamidine derivatives was successfully developed from primary amines, cyclic secondary amines, and methyl N-(3-cyano-8-methoxy-4H-[1]-benzopyran-2-yl)methanimidate as key intermediate The simplicity of the microwave protocols gave facile possibilities of isolation of the desired products by simple filtration The synthesized compounds were obtained in good yields and purity, and characterized by 1H, 13C NMR, IR, and HRMS analyses

The pseudosymmetric crystal structure of 2-(2-naphthalenyl)-3-nitro-2H-1-benzopyran, C38H26N2O6

Abstract: Abstract C19H13NO3, triclinic, P1̅ (no. 2), a = 9.4457(6) Å, b = 11.0520(7) Å, c = 14.6746(9) Å, α = 100.779(1)°, β = 102.738(1)°, γ = 93.065(1)°, V = 1460.68(16) Å3, Z = 4, Rgt(F) = 0.0410, wRref(F2) = 0.0911, T = 291 K.

Synthesis method of dihydrochalcone 1-(5,7-dihydroxyl-2,2-dimethyl benzopyran-6-)-3-(2, 2-dimethyl benzopyran-6-)-1-acetone

Abstract: The invention discloses a synthesis method of dihydrochalcone 1-(5,7-dihydroxyl-2,2-dimethyl benzopyran-6-)-3-(2, 2-dimethyl benzopyran-6-)-1-acetone. The synthesis method comprises the following steps: S1, synthesizing 6-acetyl-5, 7-dihydroxyl-2, 2-dimethyl benzopyran; S2, synthesizing 6-acetyl-5, 7-dibenzyloxy-2, 2-dimethyl benzopyran; S3, synthesizing 2, 2-dimethyl-5-formoxyl benzopyran; S4, synthesizing 1-(5, 7dibenzyloxy-2, 2-dimethyl benzopyran)-3-(2, 2-dimethyl benzopyran) chalcone; and S5, synthesizing Dihydrochalcones 1.

6-(1,3-benzimidazo-2-yl)-7-hydroxy-substituted spiro[benzopyran-indolines] having fluorescence

Abstract: FIELD: chemistry.SUBSTANCE: invention relates to novel compounds in a series of spiro[benzopyran-indolines]. Described is a 6-(1,3-benzimidazo-2-yl)-7-hydroxy-substituted spiro[benzopyran-indoline] of general formula1, where Ris C-Calkyl, Ris H, halogen.EFFECT: obtaining a novel compound containing a spirocyclic fragment, having intense fluorescence with abnormally high Stokes shift and developing photochromic properties.1 cl, 1 tbl, 2 ex

Benzopyran compound and application thereof

Abstract: The invention relates to a benzopyran compound and application thereof. The benzopyran compound has a structure formula shown in a formula I. The application is the application of the compound in preparing a biological membrane medicine for resisting the staphylococcus aureus. The formula I is shown in the description, wherein R is 3-F, 4-F, 3,5-2F, 3,4,5-3F, 4-C1, 3,4-2C1, 3-Br, and 4-Br.

Method for preparing 4H-benzopyran compound

Abstract: The invention relates to a method for preparing a 4H-benzopyran compound. The structure of the 4H-benzopyran compound is shown in figure 1, in the formula, R1, R2, R3, R4, R5, R6, R7, R8 and R9 are hydrogen atoms, alkyl, aryl, halogen, alkoxy, amino, nitryl, hydroxyl and trifluoromethyl. The method comprises the following steps: adding an acetophenone compound, a phenol compound and trifluoromethanesulfonic acid iron into a reaction tube, adding an organic solvent, or under the condition that no solvent is added, performing reaction for 1-24 hours at the room temperature to 150 DEG C, after the reaction is completed, adding an extraction agent into a reaction system, and performing extraction, filtration, concentration and column chromatography purification, thereby obtaining the 4H-benzopyran compound. The yield of the 4H-benzopyran compound is 40-90%.

Structure-activity-relationship and crystallographic analysis of 9-hydroxy-2-(2-hydroxypropan-2-yl)-2,3 dihydro-7H-furo[3,2-g]benzopyran-7-one

Abstract: The title compound C14H14O5, is a furanocoumarin [systematic name: 9-hydroxy-2-(2-hydroxypropan2-yl)-2,3-dihydro-7H-furo[3,2-g]benzopyran-7-one], which was isolated from the seeds of Apiumgraveolens (Umbelliferae), a weed cultivated in several parts of India. The compound crystallizes into monoclinic space group C2 with unit cell parameters a = 24.616(8) Å, b = 8.186(3) Å, c = 6.632(2) Å, = 103.99(2)°, Z = 4. The structure was refined by full matrix least -squares to a final R value of 0.0356 for 2216 observed reflection. The molecules are linked by O-H...O hydrogen bonds into chains and these chains are linked into sheets by C-H...O hydrogen bonds. There are also π...π interactions among the molecules which links the sheet into supramolecular structure. Structure activity predictions have been identified on the basis of structural fragments. In this compound the value of Pa (Probability of activity) is very large as compared to Pi (Probability of inactivity) for Antioxidant, Antiinflammatory and Respiratory analeptic which shows the positive influence of these descriptions.