- Cobalt-Catalyzed Dearomatization of Indoles via Transfer Hydrogenation to Afford Polycyclic Indolines
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A cobalt-catalyzed dearomatization of indoles via transfer hydrogenation with HBpin and H2O has been developed. This reaction offered a straightforward platform to access hexahydropyrido[1,2-a]indoles in high regio- and chemoselectivity. A preliminary reaction mechanism was proposed on the basis of deuterium-labeling experiments, and a cobalt hydride species was involved in the reaction.
- Chen, Siwei,Cai, Min,Huang, Junru,Yao, Hequan,Lin, Aijun
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supporting information
p. 2212 - 2216
(2021/04/05)
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- Cu-Catalyzed Oxidation of C2 and C3 Alkyl-Substituted Indole via Acyl Nitroso Reagents
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The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C-H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.
- Zhang, Jun,Torabi Kohlbouni, Saeedeh,Borhan, Babak
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supporting information
p. 14 - 17
(2019/01/08)
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- Method for preparing indole and derivatives thereof
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The invention discloses a method for preparing indole and derivatives of indole. The method for preparing indole and the derivatives of indole is characterized by comprising the following two steps that (1) a catalyst, a ligand and alkali are added in a reaction tube, under the protection of nitrogen, beta-hydroxy ketone or ester is reacted with a mixed solution of o-nitro aryl halides for 3 to 8h in an oil bath pan at the temperature of 90 to 120 DEG C, and then cooled to room temperature after reaction, and extracted, washed, dried and subjected to chromatography to obtain a product of o-nitro alpha-aryl ketone or ester; (2) o-nitro alpha-aryl ketone or ester obtained in the step (1), a reducing agent system and a solvent are added to the reaction tube, and reacted for 3 to 8h at the temperature of 60 to 100 DEG C, and then extracted, washed, dried and subjected to chromatography after being reacted to obtain a target product of indole and the derivatives of indole. Reaction raw materials, the catalyst, the ligand, the alkali and the solvent used in the invention are all industrial commodities, and simple and readily available, wide in sources, cheap in price, and further very stable in performances, and with no need for special storage conditions; in addition, the method for preparing indole and the derivatives of indole disclosed by the invention has the characteristics of low cost, high yield, simple process, less pollution and the like.
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- Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones by general Pd-catalyzed retro-aldol/α-arylation
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Divergent synthesis of indoles, oxindoles, isocoumarins and isoquinolinones is described in this report by using a general Pd-catalyzed tandem reaction of β-hydroxy carbonyl compounds with aryl halides bearing an ortho-nitro, -ester or -cyano substituent. A key retro-aldol/α-arylation reaction is involved that merges classic Pd cross-coupling chemistry with novel Pd-promoted retro-aldol C-C activation to produce α-arylated ketones or esters. Subsequent intramolecular condensation of the carbonyl with the ortho-synthon gives target heterocycles. The use of common, commercially available and cheap substrates and catalyst system adds additional synthetic advantages to the conceptual significance.
- Zhang, Song-Lin,Yu, Ze-Long
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p. 10511 - 10515
(2016/11/18)
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- Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)
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The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.
- Zhou, Han-Jie,Wang, Jinhai,Yao, Bing,Wong, Steve,Djakovic, Stevan,Kumar, Brajesh,Rice, Julie,Valle, Eduardo,Soriano, Ferdie,Menon, Mary-Kamala,Madriaga, Antonett,Kiss Von Soly, Szerenke,Kumar, Abhinav,Parlati, Francesco,Yakes, F. Michael,Shawver, Laura,Le Moigne, Ronan,Anderson, Daniel J.,Rolfe, Mark,Wustrow, David
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p. 9480 - 9497
(2016/01/12)
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- Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Carbon Monoxide as the Reductant
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An efficient catalytic cyclization of β-nitrostyrenes to indoles was developed. The reaction was applied to the synthesis of 3-arylindoles and 2-alkylindoles. Given that in the latter case the starting β-nitrostyrenes can be easily obtained by a Henry reaction, the present method allows indoles to be obtained in a two-step sequence starting from cheap reactants.
- Ferretti, Francesco,El-Atawy, Mohamed A.,Muto, Stefania,Hagar, Mohamed,Gallo, Emma,Ragaini, Fabio
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supporting information
p. 5712 - 5715
(2015/09/15)
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- PROTEASOME ACTIVITY ENHANCING COMPOUNDS
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The present invention is directed to compounds having the Formula (I), (II), (III), (IV), and (V), compositions thereof, the methods of synthesis of the compouds of interest, and to methods for the treatment of a condition associated with a dysfunction in proteostasis, such as cancer, inflammatory conditions, neurodegeneration, metabolic conditions, comprising administering an effective amount of a compound of the invention.
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Page/Page column 102
(2015/06/03)
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- Synthesis of 2,5-dihydroxy-3-(indol-3-yl)benzoquinones by acid-catalyzed condensation of indoles with 2,5-dichlorobenzoquinone
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Three methods for the conjugate addition of indoles to 2,5-dichlorobenzoquinone have been developed. A wide variety of indoles substituted with halogen, alkyl, alkoxy, and aryl groups participate in anaerobic condensation reactions promoted by HCl, H2SO4, or CH3CO2H. The hydroquinone product is partially oxidized by excess dichlorobenzoquinone and fully converted to the 2,5-dichloro-3-(indol-3-yl)benzoquinone targets by DDQ or Ag2CO3 oxidation. 2,5-Dihydroxy- 3-(indol-3-yl)benzoquinones can be obtained from the dichlorides by alkaline hydrolysis. The rotational characteristics of the biaryl bond created in these reactions have been examined by theoretical and spectroscopic methods.
- Pirrung, Michael C.,Deng, Liu,Li, Zhitao,Park, Kaapjoo
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p. 8374 - 8388
(2007/10/03)
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- Synthesis of 2,4-disubstituted indoles via thermal cyclization of N-trifluoroacetyl enehydrazines
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Synthesis of naturally occurring indoles, 2,4-dimethylindole and 4-hydroxymethyl-2-methylindole by applying thermal cyclization of N-trifluoroacetyl enehydrazines is described.
- Miyata, Okiko,Takeda, Norihiko,Naito, Takeaki
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p. 1101 - 1107
(2007/10/03)
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- 1H-INDOLE-3-ACETAMIDE SPLA2 INHIBITORS
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A class of novel 1-indole-3-acetamides represented by the formula; is disclosed together with the use of such indole compounds for inhibiting sPLA2 mediated release of fatty acids.
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- Indole Synthesis via SRN1 Reactions
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o-Haloanilines react with ketone enolate ions in ammonia under irradiation to form indoles in good yields.
- Bard, Raymond R.,Bunnett, Joseph F.
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p. 1546 - 1547
(2007/10/02)
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