Benzopyran

About: Benzopyran is a research topic. Over the lifetime, 1889 publications have been published within this topic receiving 15235 citations.

Synthetic approaches toward spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexan]-2-one derivatives via radical reactions: total synthesis of (.+-.)-lycoramine

Abstract: Syntheses of spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexan]-2-one derivatives by reaction sequences including a radical reaction and a total synthesis of (±)-lycoramine (2) are described. Radical reactions (Bu 3 SnH, AIBN) of 1-[(1'-cyclohexenylmethyl)oxy]-2-halobenzenes 23b-d in boiling benzene gave the corresponding spiro[2,3-dihydrobenzofuran-3,1'-cyclohexanes] 26a,b in good yields, whereas the reaction of 1-(1'-cyclohexenylethoxy)-2-bromobenzene (25) under similar conditions afforded a mixture of spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane] 27 and benzoxepin 28. Furthermore, the radical reaction of ethyl 2-[(2'-bromoaryl)oxy]-1-cyclohexenylacetate 37a produced ethyl 2-spiro[2,3-dihydrobenzofuran-3,1'-cycloexane]carboxylate 38 in good yield. Compound 38 was converted to spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane]-2,4'-dione 40 by treatment with SmI 2 and then with 3 N HCl. Spiro[2,3-dihydro-4H-1-benzopyran-4,1'-cyclohexane]-2,4'-dione 40 was transformed to (±)-lycoramine (2) in four steps in 43% overall yield

One-step synthesis of substituted 2-amino-5,6,7,8-tetrahydro-4H-benzo[b]pyrans. Molecular and crystal structure of 2-amino-3-(2-methoxyethoxycarbonyl)-4-(2-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran

Abstract: Substituted 2-aminobenzo[b]pyrans were synthesized by three-component condensation of aromatic aldehydes, cyanoacetic acid derivatives, and cyclic 1,3-diketones. The molecular and crystal structure of 2-amino-3-(2-methoxyethoxycarbonyl)-4-(2-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-benzo[b]pyran was established by X-ray diffraction analysis.

3-amino-3,4-dihydro-2H-1-benzopyran derivatives as 5-HT1A receptor ligands and potential anxiolytic agents. 2. Synthesis and quantitative structure-activity relationship studies of spiro[pyrrolidine- and piperidine-2,3'(2'H)-benzopyrans].

Abstract: In continuation of our work on 3-amino-3,4-dihydro-2H-1-benzopyran derivatives with high affinity for 5-HT1A receptors, we have prepared rigid spirobenzopyran analogues designed from the pharmacophore models of Mellin and selected via a quantitative structure−activity relationship approach mainly based on similarity indices. A series of spiro[pyrrolidine- and piperidine-2,3‘(2‘H)-benzopyrans] with various substitutions on the aromatic ring as well as on the extracyclic spiranic nitrogen atom were then synthesized and evaluated for their serotonergic and dopaminergic activities. Good correlation between the predicted and the experimental binding values was observed with an average difference of 0.2 unit on log(IC50). Affinities for the 5-HT1A receptors were in the nanomolar range for the best compounds ((+)-11a, 23) with a high selectivity versus other 5-HT (5-HT1B, 5-HT2, 5-HT3) or dopamine (D1, D2) receptor subtypes. As for the 3-amino-3,4-dihydro-2H-1-benzopyran series, the dextrorotatory enantiomer (+)...

Benzopyran-containing compounds and method for their use

Abstract: Certain benzopyran antiestrogens are disclosed for treating estrogen sensitive diseases such as breast cancer. Prodrug forms provide ease of manufacturing, good shelf life, and bioavailibility, and preferred stereoisomers are shown to be more effective than racemic mixtures.