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: Experimental evidence is provided to support the hypothesis that a hetero Diels-Alder cycloaddition between an o-quinone methide intermediate with a simple, or activated tri-substituted olefin is involved in the biogenesis ofLucidene and alboatrin.
Abstract: Lucidene and alboatrin are complex benzopyran derived natural products. A key step in their biogenesis may involve a hetero Diels–Alder cycloaddition between an o-quinone methide intermediate with a simple, or activated tri-substituted olefin. Experimental evidence is provided to support this hypothesis, with the biomimetic synthesis of both (±)-lucidene and (±)-alboatrin successfully achieved using a new and efficient method for o-quinone methide generation.
48 citations
TL;DR: The synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed and the activity of 2a in the mouse capsaicin assay seems to indicate sigma 1 antagonistic activity.
Abstract: Herein, the synthesis and pharmacological evaluation of thiophene bioisosteres of the highly potent spirocyclic benzopyran 1 are detailed. The synthesis of 1-benzyl-6′-methoxy-6′,7′-dihydrospiro[piperidine-4,4′-thieno[3.2-c]pyran] (2a) was performed starting with 3-bromothiophene (3). After introduction of the acetaldehyde substructure (7), halogen metal exchange, addition of 1-benzylpiperidin-4-one, and cyclization led to the spirocyclic thienopyran 2a. The removal of the benzyl group afforded the secondary amine 2f, which was substituted with various residues. With respect to σ1 affinity the N-benzyl derivative 2a, the N-cyclohexylmethyl derivative 2d, and the N-p-fluorobenzyl derivative 2i represent the most potent compounds of this series binding with Ki values of 0.32, 0.29, and 0.62 nM, respectively. Electronic properties of the substituents have only little impact on σ1 affinity. The most potent σ1 ligands display high selectivity against σ2, 5-HT1A, 5-HT6, 5-HT7, α1A, α2, and NMDA receptors. The a...
48 citations
TL;DR: In this paper, 1-Benzopyran-4(4H)-one derivatives have been successfully employed as novel activated alkenes in the Baylis-Hillman coupling with heteroaromatic-aldehydes, nitrobenzaldehes and isatin-derivatives and the corresponding adducts, derived from pyridine-2-carboxaldehyde, have been transformed into a novel indolizine-fused-chromone framework.
48 citations
TL;DR: One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel
Abstract: A series of 4-amido-3,4-dihydro-2H-1-benzopyran-3-ols and 4-amido-2H-1-benzopyrans related to the potassium channel activator cromakalim have been prepared and evaluated for their relaxant activity in guinea pig isolated tracheal spirals. Several analogues show enhanced relaxant activity relative to cromakalim in this preparation and the rank order of potency for those substituents investigated at C-6 was CF3 greater than CN greater than C2H5 greater than aza greater than or equal to CH3. One compound, trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-7-(trifluor omethyl)-2H- 1-benzopyran-3-ol (24), was resolved into its two enantiomers and the activity was shown to reside essentially in the (+)-isomer, adding further support to the suggestion that the smooth muscle receptor for these potassium channel activators is stereoselective.
48 citations
47 citations