6H-Benzo[c]chromen-6-one derivatives as selective ERβ agonists

Sun, Wanying; Cama, L. D.; Birzin, Elizabeth T.; Warrier, Sudha; Locco, Louis; Mosley, Ralph T.; Hammond, Milton L.; Rohrer, Susan P.

doi:10.1016/j.bmcl.2005.12.057

Cited by 133 publications

(37 citation statements)

References 13 publications

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“…For applications of benzo[c]chromen-6-ones, see: Schmidt et al (2003); Pandey et al (2004); Matsumoto & Hanawalt (2000); Sun et al (2006). For the synthesis, see : Fan et al (2012).…”

Section: Related Literaturementioning

confidence: 99%

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3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

Cui

Fan

2013

Acta Cryst E

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Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.006 Å; R factor = 0.077; wR factor = 0.229; data-to-parameter ratio = 12.7.In the title compound, C 13 H 10 O 3 , the pyranone and benzene rings are almost coplanar, making a dihedral angle of 1.9 (1) . The cyclohexenone ring adopts an envelope conformation, with a methylene C atom located at the flap and displaced by 0.639 (3) Å from the mean plane of the other five atoms. In the crystal, pairs of weak C-HÁ Á Á interactions occur between inversion-related molecules. Related literature ExperimentalCrystal data Table 1 Hydrogen-bond geometry (Å , ).Cg is the centroid of the C1-C6 benzene ring. organic compounds o754 Cui et al.

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“…For applications of benzo[c]chromen-6-ones, see: Schmidt et al (2003); Pandey et al (2004); Matsumoto & Hanawalt (2000); Sun et al (2006). For the synthesis, see : Fan et al (2012).…”

Section: Related Literaturementioning

confidence: 99%

“…Benzo[c]chromen-6-ones constitute one of the major classes of pharmacologically relevant natural products and display a wide range of biological activities (Schmidt et al, 2003;Pandey et al, 2004;Matsumoto et al, 2000;Sun et al, 2006).…”

Section: S1 Commentmentioning

confidence: 99%

3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

Cui

Fan

2013

Acta Cryst E

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“…It is one of the privileged scaffolds with a medicinal pharmacophore such as antivascular, antimicrobial, antioxidant, anticoagulant, estrogenic, anti-helminthic, anticancer 1 , anti-HIV, anti-inflammatory 2 , analgesic, herbicidal 3 and anticonvulsant. Chromenes are an important natural occurring compound such as flavonoids, alkaloids, tocopherol and anthocyanin [4][5][6] . Benzo[g]chromene contains naphthoquinone structural motifs which also have a broad spectrum in biological activities, as molecular probes for biochemical research 7 , emitters in electroluminescence devices and as fluorescent whitening agents 8 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and In Vitro Antibacterial Effect of 4H-Benzo[g]chromene Derivatives using Nano-NiO

2017

Chem Sci Trans

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Abstract:The domino Knoevenagel cyclocondensation reactions via substituted aldehydes, activated methylene reagent and 2-hydroxy-1, 4-naphthoquinone gives benzo[g]chromenes in presence of nano-NiO using acetonitrile as a solvent at ambient temperature. This method gives the desired products from good to excellent yield. The salient features of this atom economical procedure are ease of manipulation, simpler workup, high yield processing, easy handling, inexpensiveness, reusability of catalyst and tolerance to a wide range of functional groups. The synthesized chromene derivatives are screened for antibacterial activity and antifungal activity using Kirby-Bauer method. The synthesized compounds 3a-3k exhibits significant inhibition to antibacterial and antifungal activity compared with the standard drug Ciprofloxacin and Flucanazole respectively.

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“…Sun and coworkers treated phenol 17 with o -benzoic acids 18, catalyzed by CuSO 4 in the presence of NaOH 19,20 as shown in Scheme 1, while in the alternative method o-benzoic acid ester (21) was coupled to aryl boronic acid using (Ph 3 P) 4 Pd as catalyst. The cyclization was achieved after deprotecting the methyl group of the biphenyl with BBr 20 3 as shown in Scheme 2.…”

Section: Metal-catalyzed Reactions Involving Phenolsmentioning

confidence: 99%

Synthetic protocols on 6$H$-benzo[$c$]chromen-6-ones: a review

Mazimba¹

2016

Turk J Chem

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6 H -Benzo[ c ]chromen-6-ones serve as core structures of secondary metabolites and are of considerable pharmacological importance. Natural sources produce limited quantities, hence the need for synthetic procedures for 6 H -benzo[ c ]chromen-6-ones, which are herein reviewed. The literature describes protocols such as the Suzuki coupling reactions for the synthesis of biaryl, which then undergoes lactonization, reactions of 3-formylcoumarin (chromenones) with 1,3-bis(silylenol ethers), radical mediated cyclization of arylbenzoates, metal or base catalyzed cyclization of phenyl-2-halobenzoates and 2-halobenzyloxyphenols, and benzoic acid coupling with benzoquinone using electrophilic metalbased catalyst. The efficient and simple procedures are those involving the reactions of Michael acceptor (chromenones and chalcones) with 1,3-and 1,5-dicarbonyl compounds.

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6H-Benzo[c]chromen-6-one derivatives as selective ERβ agonists

Cited by 133 publications

References 13 publications

3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

3,4-Dihydro-1H-benzo[c]chromene-1,6(2H)-dione

Synthesis, Characterization and In Vitro Antibacterial Effect of 4H-Benzo[g]chromene Derivatives using Nano-NiO

Synthetic protocols on 6$H$-benzo[$c$]chromen-6-ones: a review

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