Topic
Benzopyran
About: Benzopyran is a research topic. Over the lifetime, 1889 publications have been published within this topic receiving 15235 citations.
Papers published on a yearly basis
Papers
More filters
TL;DR: New potent and selective lead compounds with improved metabolic properties were identified and binding free energies predicted by free energy perturbation theory yielded good agreement with experimental results.
11 citations
TL;DR: A novel class of 1'-cyclobutyl-6-(4-piperidyloxy)spiro[benzopyran-2,4'-piperidine] derivatives with low nanomolar affinity for the human and rat histamine-3 receptors (H(3)Rs) are described.
11 citations
TL;DR: In this paper, the synthesis of carbon-phosphorus-containing precursors of cannabinoids has been reported, which are the first reported in this family of carbonophosphorus heterocycles, and a single-crystal X-ray diffraction analysis of the pentyl derivative confirmed the structure.
Abstract: The syntheses of l,2,3,4-tetrahydro-10-hydroxy-8-methyland l,2,3,4-tetrahydro-10-hydroxy-8-w-pentyl-3phenyl-5#-phosphorino[3,4-c] [l]benzopyran-5-one 3-oxide have been achieved. These precursors of cannabinoid analogues are the first reported in this family of carbon-phosphorus heterocycles. A single-crystal X-ray diffraction analysis of the pentyl derivative confirmed the structure. H, C, and P NMR analyses are also supportive of the basic assignments for both compounds. An intermediate synthon methyl 4-oxo-l-phenyl-3-phosphorinanecarboxylate was analyzed via H, C, and P NMR spectroscopy and was found to exist primarily in an enol form in solution and had different properties than previously reported. Considerable activity in the chemistry of cannabinoids, in particular heteroatom-substituted derivatives, in recent years and our interest in carbon-phosphorus heterocycles which are analogues of natural products prompt us to reveal our results on certain phosphorus-containing precursors of cannabinoids. We report herein the synthesis of l,2,3,4-tetrahydro-10-hydroxy-8methyl(1) and l,2,3,4-tetrahydro-10-hydroxy-8-n-pentyl-3phenyl-5#-phosphorino[3,4-c][l]benzopyran-5-one 3-oxide (2). analysis (KBr pellet) showed a broad band at 3350 cm assigned to an 0 H stretching frequency of an enol. A small peak at 1725 cm also inferred the presence of a carbonyl group. The band at 1639 cm\" was of medium intensity and was supportive of the conjugated double bond present in the enol form. H NMR analysis of 4b was complex (see Table I) although the protons of the methyl group appeared at 5 3.78. Indeed, the C NMR spectrum of 4b was not simple and the interpretation was best in accord with a very high population of the enol form 5. In Table I, there are two signals for sp-hybridized carbons C(3) and C(4) located at 92.78 ppm ( 2 / r c = 3.90 Hz) and 172.07 ppm (/pc = 9.62 Hz), respectively. The other resonances seem reasonable. The C NMR signal pattern did not change for a solution of 4b in DCCl3 at room temperature down to -70 C. CHo CHoCH oCHoCH'a A 2 B C D Z . 3 Bis(2-(carbomethoxy)ethyl)phenylphosphine (3) was converted
11 citations
TL;DR: Five new benzopyran derivatives and a new natural product isolated from endophytic Daldinia eschscholzii in Dendrobium chrysotoxum and evaluated for their antimicrobial activity, anti-acetylcholinesterase, nitric oxide inhibition, anticoagulant, photodynamic antimicrobial activities and glucose uptake of adipocytes.
11 citations
TL;DR: In this paper, structural information on the influence of substitution of intracyclic and glycosidic oxygen atoms by sulfur atoms, as well as on influence of aromatic rings and of sulfoxide groups on the carbohydrate moiety is provided.
11 citations