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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: Significant potentiation of growth inhibitory activity was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP 1A1 bioactivation.
Abstract: A new series of fluoro-, methoxyl-, and amino-substituted isoflavones have been synthesized as potential antitumor agents based on structural similarities to known flavones and isoflavones (quercetin and genistein respectively) and antitumor 2-phenylbenzothiazoles Target compounds were synthesized using palladium-catalyzed coupling methodologies to construct the central aryl carbon-carbon single bond The new isoflavone derivatives were tested for in vitro activity in human breast (MDA-MB-468 and MCF-7) and colon (HT29 and HCT-116) cancer cell lines Low micromolar GI50 values were obtained in a number of cases, with the MDA-MB-468 cell line being the most sensitive overall Notably, significant potentiation of growth inhibitory activity (GI50<1 microM for 12d, 12f, 12h, 12k, 12l, 12o but not the methylene-bridged derivative 12i) was observed when MDA-MB-468 cells were co-incubated with TBDD, a powerful inducer of cytochrome P450 (CYP)-1A1 activity, suggesting that isoflavone derivatives can act as substrates for CYP1A1 bioactivation
76 citations
TL;DR: Various aliphatic aldehydes and substituted (E)-2-(2-nitrovinyl)phenols were proven to be well tolerated in this tandem reaction and could be conveniently transformed to synthetically and biologically significant chiral dihydrocoumarin, chroman, and 4H-chromene derivatives.
Abstract: Asymmetric tandem Michael addition−hemiacetalization between aliphatic aldehydes and (E)-2-(2-nitrovinyl)phenols was investigated for constructing benzopyran backbones. Interestingly, the diastereo- and enantioselectivities changed markedly when the reaction was mediated by different types of secondary amine catalysts. The diphenylprolinol silyl ether 7 promoted the reaction with excellent enantioselectivities (up to 99% ee) but with moderate diastereoselectivities (2.8:1 to 10:1). Prolylprolinols are another type of efficient catalyst. Among them, l,l-prolylprolinol 5c is identified as the optimal species, showing high catalytic activity, good enantioselectivities (up to 89% ee), and excellent diasereoselectivities (up to 50:1 dr). Various aliphatic aldehydes and substituted (E)-2-(2-nitrovinyl)phenols were proven to be well tolerated in this tandem reaction. In addition, the chroman-2-ols 3 yielded in the above reactions could be conveniently transformed to synthetically and biologically significant chi...
72 citations
TL;DR: The ortho-iodoaryl allyl ethers derived from 1 via the aromatic directed metalation protocol, undergo tributyl tin hydride-induced heteroring annelation to lead to unusually substituted benzofuran (3) and benzopyran, and furopyridine derivatives (Table).
69 citations
TL;DR: A metal-free reaction has an excellent functional group tolerance and high chemoselectivity and displays a broad scope with respect to both benzopyran and nucleophile partners, efficiently affording a collection of Benzopyrans bearing diverse skeletons and α-functionalities in one step.
69 citations
TL;DR: A number of carbonyl and phenolic compounds efficiently couple with o-dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds.
Abstract: A number of carbonyl and phenolic compounds efficiently couple with o-dibromobenzenes in the presence of a palladium catalyst and a base to give the corresponding oxygen-containing heterocycles or carbocyclic compounds. Thus, from the reactions of benzyl phenyl ketones, 1-naphthols, and α,β-unsaturated aldehydes and ketones, benzofuran, benzopyran, benzocyclobutane, and indene derivatives, respectively, are produced selectively via the successive formation of C–C and C–O bonds or of two C–C bonds.
66 citations