Topic
Benzopyran
About: Benzopyran is a research topic. Over the lifetime, 1889 publications have been published within this topic receiving 15235 citations.
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TL;DR: In this article, the authors showed that the marked influence of an electron withdrawing 3-substituent in 5 is demonstrated by the fluorescence spectra of 7a,b (synthesized from 2d,e and ethyl 3-oxobutyrate), whose maxima are sharply shifted to the blue as compared with compounds 21-r.
54 citations
TL;DR: The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim are described, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus.
Abstract: The synthesis and antihypertensive activity in the spontaneously hypertensive rat of two new series of analogues related to cromakalim (1) are described. In the first series, where the benzopyran nucleus has been replaced by a pyranopyridine nucleus, the position of the nitrogen atom has been found to be critical for activity, and the most potent compounds are the pyrano[3,2-c]pyridines. In the second series, where the powerful electron-withdrawing cyano group of compound 1 has been replaced by alkyl and phenyl groups, the order of antihypertensive potency is ethyl, isopropyl, tert-butyl greater than propyl, cyclopentyl greater than methyl greater than phenyl.
54 citations
TL;DR: In this article, benzo-fused heterocycles such as indoles, benzofurans, and a benzopyran were obtained using an intramolecular cross-coupling of vinyl halides with phenols.
54 citations
TL;DR: The results suggest that the resorcinol series represent a novel template for the development of CB( 2)-selective cannabinoid agonists that have the potential to offer insights into similarities and differences between structural requirements for receptor recognition at CB(1) and CB(2) receptors.
Abstract: The role of the oxygen of the benzopyran substituent of Δ9-tetrahydrocannabinol in defining affinity for brain cannabinoid (CB1) receptors is not well understood; however, it is known that opening the pyran ring can result in either increased potency and affinity, as in CP 55,940 [(−)- cis- 3-[2-hydroxy-4(1,1- dimethyl-heptyl)phenyl]- trans- 4-(3-hydroxy-propyl)cyclohexanol], or in an inactive cannabinoid, as in cannabidiol. In the present study, a series of bicyclic resorcinols that resemble cannabidiol were synthesized and tested in vitro and in vivo. Analysis of the structure-activity relationships of these analogs revealed several structural features that were important for maintaining CB1receptor recognition and in vivo activity, including the presence of a branched lipophilic side chain and free phenols as well as substitution of a cyclohexane as the second ring of these bicyclic cannabinoids. Many of these analogs exhibited CB2 selectivity, particularly the dimethoxyresorcinol analogs, and this selectivity was enhanced by longer side chain lengths. Hence, unlike cannabidiol, these resorcinol derivatives had good affinity for CB1 and/or CB2 receptors as well as potent in vivo activity. These results suggest that the resorcinol series represent a novel template for the development of CB2-selective cannabinoid agonists that have the potential to offer insights into similarities and differences between structural requirements for receptor recognition at CB1 and CB2 receptors.
54 citations
TL;DR: Synthese a partir d'hydraxy-3 phtolides and de nitro-1 alcanes via des acides nitro 2' alkyl-2 benzoiques as mentioned in this paper.
Abstract: Synthese a partir d'hydraxy-3 phtolides et de nitro-1 alcanes via des acides nitro-2' alkyl-2 benzoiques
53 citations