- Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones
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An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20?mol?% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.
- Meraz, Kevin,Gnanasekaran, Krishna Kumar,Thing, Rup,Bunce, Richard A.
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supporting information
p. 5057 - 5061
(2016/11/02)
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- TRPV1 ANTAGONISTS
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Disclosed herein are compounds of Formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.
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Page/Page column 52
(2010/04/30)
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- TRPV1 ANTAGONISTS
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Disclosed herein are compounds of formula (I), or pharmaceutically acceptable salts, solvates, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, R4, and m are defined in the specification. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.
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Page/Page column 50-51
(2010/04/30)
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- Discovery of novel benzopyranyl tetracycles that act as inhibitors of osteoclastogenesis induced by receptor activator of NF-κB ligand
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A novel benzopyran-fused molecular framework 7ai was discovered as a specific inhibitor of RANKL-induced osteoclastogenesis using a cell-based TRAP activity assay from drug-like small-molecule libraries constructed by diversity-oriented synthesis. Its inhibitory activity was confirmed by in vitro evaluations including specific inhibition of RANKL-induced ERK phosphorylation and NF-κB transcriptional activation. 7ai can serve as a specific small-molecule modulator for mechanistic studies of RANKL-induced osteoclast differentiation as well as a potential lead for the development of antiresorptive drugs.
- Zhu, Mingyan,Kim, Myung Hee,Lee, Sanghee,Bae, Su Jung,Kim, Seong Hwan,Park, Seung Bum
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supporting information; experimental part
p. 8760 - 8764
(2011/02/23)
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- Antidiabetic and antiobesity effects of ampkinone (6f), a novel small molecule activator of AMP-activated protein kinase
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Adenosine 5'-monophosphate (AMP) activated protein kinase (AMPK) has emerged as an attractive target molecule for the treatment of metabolic disorders, including obesity and type 2 diabetes. In this study, we identified a novel small molecule, ampkinone (
- Oh, Sangmi,Kim, Sung Jin,Hwang, Jung Hwan,Lee, Hyang Yeon,Ryu, Min Jeong,Park, Jongmin,Kim, Soung Jung,Jo, Young Suk,Kim, Yong Kyung,Lee, Chul-Ho,Kweon, Ki Ryang,Shong, Minho,Park, Seung Bum
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supporting information; experimental part
p. 7405 - 7413
(2011/01/12)
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- 6-SUBSTITUTED PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES
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Compounds of Formula (I): in which A1, A2, W, L, G, R7a, R7b, R8, R9 and R10 have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.
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Page/Page column 73
(2010/01/30)
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- Prodrugs of compounds that inhibit TRPV1 receptor
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Compounds of formula (I) wherein A, R1, R2, and R3 are defined in the specification, and which are useful as therapeutic compounds particularly for treating disorders or conditions associated with inflammation, pain, bladd
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Page/Page column 31
(2010/11/27)
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- Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
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Compounds that are antagonists of the VR1 receptor, having formula (I) [image] or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A1, A2, A3, A4, R7, R8, R9, X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.
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Page/Page column 42
(2008/06/13)
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- CHROMAN DERIVATIVES AND THEIR USE AS 5-HT RECEPTOR LIGANDS
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Compounds of the formula (I) or pharmaceutically acceptable salts thereof, wherein m, p, q, Ar, R1, R2, R3 and R4 are as defined herein. Also provided are methods for preparing, compositions comprising, and methods for using compounds of formula (I).
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Page/Page column 32
(2008/06/13)
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- CHROMAN DERIVATIVES AND USES THEREOF IN THE TREATMENT OF CNS DISORDERS
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Compounds of the formula (I): or pharmaceutically acceptable salts thereof, wherein m, p, q, Ar, R1, R2, R3 and R4 are as defined herein. Also provided are methods for preparing, compositions comprising, and met
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Page/Page column 26
(2008/06/13)
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- Cyclization of 3-Fluorophenol and 3,3-Dimethylacrylic Acid: A Structure Correction
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Reaction of 3-fluorophenol and 3,3-dimethylacrylic acid in methanesulfonic acid at 90 deg C gives predominantly 5-fluoro-2,2-dimethylchroman-4-one, not the 7-fluoro isomer as reported.
- Shawcross, Frances,Sard, Howard
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p. 1393 - 1396
(2007/10/03)
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