Showing papers on "Benzopyran published in 2021"
TL;DR: In this article, six new metabolites, including two diphenolic derivatives (1 and 2), one pseurotin (3), one butenolide derivative (4), one benzopyran (5) and one isochromane lactone (6), together with ten known compounds (7, 16) were isolated from an endophytic fungus Aspergillus sp.
11 citations
10 citations
TL;DR: In this paper, the authors investigated the relationship between the structures of 1-aminoethyl-substituted chromenes and their antimalarial activities and found that 1-Benzopyran-5-ol 8b (IC50 = 10 nM), 1-benzopyrans-7-ol 9c (IC 50 = 38 nM) and aminoalcohol 19c (IWC) exhibited antiplasmodial activity with IC50 values below 50 nM.
Abstract: Herein, relationships between the structures of 1-aminoethyl-substituted chromenes and their antimalarial activities were thoroughly investigated. At first, the methyl moiety in the side chain was removed to eliminate chirality. The hydrogenation state of the benzopyran system, the position of the phenolic OH moiety, and the distance of the basic amino moiety toward both aromatic rings were varied systematically. 1-Benzopyran-5-ol 8b (IC50 = 10 nM), 1-benzopyran-7-ol 9c (IC50 = 38 nM), and the aminoalcohol 19c (IC50 = 17 nM) displayed antiplasmodial activity with IC50 values below 50 nM. To identify the mechanism of action, inhibition of three key enzymes by 9c was investigated. 9c was not able to reduce the number of Plasmodia in erythrocytes of mice. This low in vivo activity was explained by fast clearance from blood plasma combined with rapid biotransformation of 9c. Three main metabolites of 9c were identified by liquid chromatography-mass spectrometry (LC-MS) methods.
5 citations
3 citations
TL;DR: In this paper, the authors synthesized 38 coumarin derivatives by substituting carbon 8 of the benzopyran ring with some aromatic and aliphatically substituted piperidines and piperazines.
Abstract: Coumarins (2H-1-benzopyran-2-one), derivatives that can be isolated from several plants, have been reported for their anticoagulant, antimicrobial, anti-inflammatory, or anticancer activity. Some of these structures are currently approved for the treatment of cardiovascular diseases, as antibiotics or as an anticancer drug. Given the great potential of this structure and the limited number of studies that focus on molecules derived from carbon 8 of the benzopyranone heterocycle, we synthesized in this project 38 coumarin derivatives by substituting carbon 8 of the benzopyran ring with some aromatic and aliphatically substituted piperidines and piperazines. As a few of these structures were already shown to exhibit some carbonic anhydrase (CA) inhibition and as CA enzymes are reported to be closely related to inflammation, the synthesized derivatives were evaluated for their anti-inflammatory activity in vitro. The results indicated that compounds 20 and 31 revealed promising anti-inflammatory activity, as they demonstrated better activity than the reference drugs.
3 citations
2 citations
TL;DR: One new spirocyclic lactone, terreinlactone C, and one new benzopyran derivative, 2,2-dimethyl-3-hydroxychroman-6-aldehyde, were discovered from the fungus Aspergillus terreus by detailed analyzing NMR and HRESIMS data.
2 citations
TL;DR: In this paper, a series of substituted dihydro-1, 2-oxazole benzopyran-2-one (SR1-SR6) were synthesized through the intermediate substitutions of substituted benzoprin-1-one chalcones and were characterized using spectral analysis.
Abstract: A series of substituted dihydro-1, 2-oxazole benzopyran-2-one (SR1-SR6) were synthesized through the intermediate substituted benzopyran-2-one chalcones and were characterized using spectral analysis. Compounds were docked with receptor DNA Gyrase B (PDB code: 5L3J) to know its interaction and binding energy; ranges -3.38 to -2.15 kcal/mol. Further these compounds were tested for antibacterial activity using tube dilution method and MIC values were observed; ranges 3.12 to 25 µg/ml. Compound 3-(5-(m-tolyl)-4,5-dihydroisoxazol-3-yl)-2H-chromen-2-one (SR3) showed the best interaction with binding energy -3.38 kcal/mol and antimicrobial activity having MIC 3.12 µg/ml.
GRAPHICAL ABSTRACT
2 citations
TL;DR: Two new compounds, a rearranged limonoid and a benzopyran (harriforanone), were isolated from the leaves and stems of Harrisonia perforata (Blanco) Merr, together with three known limonoids and fourteen known chromones as discussed by the authors.
1 citations
TL;DR: A photochromic supramolecular complex of benzopyran containing benzo-18-crown-6-ether 1 with 4-aminonaphthalimide 2 as a fluorophore is presented in this article.
Abstract: We present here design, preparation, characterization, and properties of a photochromic supramolecular complex of benzopyran containing benzo-18-crown-6-ether 1 with 4-aminonaphthalimide 2 as a fluorophore. Phototransformation of the supramolecular complex 1⋅2 is accompanied by the appearance of a predominantly open TC form, which is consistent with the monoexponential bleaching curve of an open form at room temperature. Compared with free benzopyran 1, the bleaching rate is increased by 5–6 times in the presence of 2. From a synthetic point of view, varying the components in the supramolecular complex is more preferable to obtain a system with the desired characteristics. Thus, this study demonstrates that the supramolecular approach is promising for systems that contain photochromic and fluorescent components that influence each other.
1 citations
TL;DR: In this article, photochromic spirobipyrans bearing benzoxazole group in the 3H-naphthopyran fragment have been synthesized.
Abstract: Novel photochromic spirobipyrans bearing benzoxazole group in the 3H-naphthopyran fragment have been synthesized. Spiro-conjugated benzopyran and naphthopyran fragments cause the observed dual photochromism of the molecules. In the presence of Cd2+, Mn2+, Co2+, Ni2+, Zn2+, Cu2+ metal ions thermal isomerization of the spirobipyrans is observed, followed by the formation of the intensely coloured complexes of the merocyanine form. The long-wavelength absorption band of the complexes is located at λ>600 nm.
04 Mar 2021
TL;DR: The main functions of σ 1 receptors include the modulation of release and reuptake of neurotransmitters, the regulation of ion channels and the influence on intracellular signaling through modulation of calcium levels.
Abstract: The main functions of σ1 receptors include the modulation of release and reuptake of neurotransmitters, the regulation of ion channels and the influence on intracellular signaling through modulation of calcium levels. Due to these properties, σ1 receptors are interesting drug targets for the treatment of various neurological disorders, pain and cancer. In order to modify the distance between the pharmacophoric elements (the benzene ring of 2-benzopyran and an amino moiety), a set of spiro[[2]benzopyran-1,1′-cyclohexan]-3′-amines was synthesized. The key step of the synthesis was a Parham cyclization of 1-bromo-2-(2-bromoethyl)benzene (6) with the mono ketal 7 of cyclohexane-1,3-dione, which led in a one-pot reaction to the spirocyclic framework 8. Reductive amination of ketone 9 stereoselectively provided secondary amines cis-4, which were methylated to afford tertiary amines cis-5. Whereas spirocyclic compounds cis-4a and cis-5a bearing a benzyl moiety at the exocyclic amino moiety showed rather low σ1 affinity, the corresponding cyclohexylmethyl derivatives cis-4b and cis-5b exhibited low nanomolar σ1 affinity. The secondary amine cis-4b displayed the highest σ1 receptor affinity (Ki = 5.4 nM) in this series. Methylation of the secondary amine cis-4b led to a slightly decreased σ1 receptor affinity of cis-5b (Ki = 15 nM).
Patent•
01 Apr 2021
TL;DR: A class of compounds that have a pyrazine structure, specifically disclosed is a compound represented by formula (VII), isomers or pharmaceutically acceptable salts thereof, and an application thereof in the preparation of CRAC inhibitors as mentioned in this paper.
Abstract: A class of compounds that have a pyrazine structure, specifically disclosed is a compound represented by formula (VII), isomers or pharmaceutically acceptable salts thereof, and an application thereof in the preparation of CRAC inhibitors.
Patent•
16 Mar 2021
TL;DR: In this paper, a benzopyran urea compound with a novel structure was obtained through multi-step reaction, so that the synthesis method is simple, and the reaction yield is very high.
Abstract: The invention discloses a preparation method and application of a benzopyran urea compound capable of being used for sterilization and disinfection, and belongs to the technical field of synthesis ofantibacterial drugs. According to the technical scheme, the benzopyran urea compound is characterized in that the benzopyran urea compound has a structure, wherein R1 is alkyl or olefin or aryl, benzyl or heterocyclic ring with different substituent groups; R2 is an oxygen or sulfur atom. Benzopyran-4-ketone is used as an initial raw material, and the benzopyran urea compound with a novel structure is obtained through multi-step reaction, so that the synthesis method is simple, and the reaction yield is very high. An antibacterial activity test is carried out through an oxford cup agar diffusion method, and it is found that the target compound has a certain inhibition effect on staphylococcus aureus and has the potential of serving as an antibacterial drug.