- Natural product inspired library synthesis - Identification of 2,3-diarylbenzofuran and 2,3-dihydrobenzofuran based inhibitors of Chlamydia trachomatis
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A natural product inspired library was synthesized based on 2,3-diarylbenzofuran and 2,3-diaryl-2,3-dihydrobenzofuran scaffolds. The library of forty-eight compounds was prepared by utilizing Pd-catalyzed one-pot multicomponent reactions and ruthenium-catalyzed intramolecular carbenoid C-H insertions. The compounds were evaluated for antibacterial activity in a panel of test systems including phenotypic, biochemical and image-based screening assays. We identified several potent inhibitors that block intracellular replication of pathogenic Chlamydia trachomatis with IC50 ≤ 3 μM. These new C. trachomatis inhibitors can serve as starting points for the development of specific treatments that reduces the global burden of C. trachomatis infections.
- Saleeb, Michael,Mojica, Sergio,Eriksson, Anna U.,Andersson, C. David,Gylfe, ?sa,Elofsson, Mikael
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supporting information
p. 1077 - 1089
(2017/12/15)
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- One-pot synthesis of 2,3-disubstituted benzofurans from 2-chlorophenols using palladium–dihydroxyterphenylphosphine catalyst
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2,3-Disubstituted benzofurans possessing 2-hydroxyphenyl moiety at the C-3 position were synthesized from readily available 2-chlorophenols and terminal alkynes by hydroxy-directed ortho-Sonogashira coupling and subsequent oxypalladation/reductive elimina
- Yamaguchi, Miyuki,Ozawa, Hayato,Katsumata, Haruka,Akiyama, Tomoyo,Manabe, Kei
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supporting information
p. 3175 - 3178
(2018/07/15)
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- Fluorination of 2-substituted benzo[b]furans with Selectfluor
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An efficient protocol was developed to access 3-fluoro-2-hydroxy-2-substituted benzo[b]furans with Selectfluor as the fluorinating reagent in MeCN and water. By utilizing SOCl2/Py as the dehydrating agent, the compounds above were readily conve
- Wang, Mingliang,Liu, Xixi,Zhou, Lu,Zhu, Jidong,Sun, Xun
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supporting information
p. 3190 - 3193
(2015/03/18)
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- N-Heterocyclic Carbene-Palladium(II)-1-Methylimidazole Complex Catalyzed Direct C-H Bond Arylation of Benzo[b]furans with Aryl Chlorides
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The first example of sole direct C-H bond arylation of benzo[b]furans with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the suitable conditions, all reactions involving kinds of benzo[b]furans and (hetero)aryl chlor
- Yin, Shun-Chao,Zhou, Quan,Zhao, Xiao-Yun,Shao, Li-Xiong
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p. 8916 - 8921
(2015/09/15)
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- Highly asymmetric synthesis of (+)-corsifuran A. Elucidation of the electronic requirements in the Ruthenium-NHC catalyzed hydrogenation of benzofurans
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A short and efficient synthesis of ent-corsifuran A by a highly asymmetric hydrogenation of a benzofuran precursor is reported. In addition, the electronic influence of the substituents on the asymmetric hydrogenation of benzofurans is provided. Whereas the hydrogenation of electron-deficient benzofurans was achieved under very mild conditions, the presence of electron-donating groups in the benzofuran required harsher reaction conditions for achieving full conversion to the 2,3-dihydrobenzofuran.
- Ortega, Nuria,Beiring, Bernhard,Urban, Slawomir,Glorius, Frank
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p. 5185 - 5192
(2012/07/31)
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- PHARMACEUTICAL COMPOSITIONS AND METHODS OF PREVENTING, TREATING, OR INHIBITING INFLAMMATORY DISEASES, DISORDERS, OR CONDITIONS OF THE SKIN, AND DISEASES, DISORDERS, OR CONDITIONS ASSOCIATED WITH COLLAGEN DEPLETION
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The present invention provides compositions and methods for preventing, treating, or inhibiting inflammatory diseases, disorders, or conditions of the skin, and diseases, disorders, or conditions associated with collagen depletion using one or more estrogenic agents.
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- Substituted 2-phenyl benzofurans as estrogenic agents
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This invention provides estrogen receptor modulators of formula I, having the structure wherein R, R′, A, A′, X, Y, and Y are as defined in the specification, or a pharmaceutically acceptable salt thereof.
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- Synthesis of 2-substituted benzofurans and indoles using functionalized titanium benzylidene reagents on solid phase
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Titanium(IV) benzylidenes bearing a masked oxygen or nitrogen nucleophile in the ortho position were generated from thioacetals, using low-valent titanocene complex, Cp2Ti[P(OEt)3]2. Methylene acetal, alkyl ether, silyl ether, fluoro, tertiary amino, and N-alkyl, N-benzyl, N-prenyl, and N-silyl tert-butyl carbamate groups were tolerated in the titanium alkylidene reagents (Schrock carbenes). Aryl-chlorine bonds were stable to the titanium benzylidene functionality, but there was poor chemoselectivity for the reduction of the thioacetal in the presence of an aryl chloride. The titanium benzylidenes converted Merrifield and Wang resin-bound esters into enol ethers. The oxygen nucleophile was masked as a TMS ether, and when the resin-bound enol ethers bearing this ortho substituent were treated with 1% TFA in dichloromethane, benzofurans were released from resin in high yields. The chameleon catch strategy ensured excellent purity. In a similar way, N-alkylated and N-silylated tert-butyl carbamates were used for the synthesis of N-alkyl and N-Boc indoles, respectively. These traceless solid-phase syntheses of heterocycles are believed to involve post-cleavage modification rather than cyclative termination.
- Macleod, Calum,McKiernan, Gordon J.,Guthrie, Emma J.,Farrugia, Louis J.,Hamprecht, Dieter W.,Macritchie, Jackie,Hartley, Richard C.
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p. 387 - 401
(2007/10/03)
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