- Synthesis of 3-acylindoles by oxidative rearrangement of 2-aminochalcones using a hypervalent iodine reagent and cyclization sequence
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An efficient one-pot method was developed for the construction of 3-acylindoles via oxidative rearrangement of 2-aminochalcones followed by intramolecular cyclization. The reaction was used to convert a variety of 2-aminochalcones into 3-acylindoles in mo
- Nakamura, Akira,Tanaka, Satoshi,Imamiya, Akira,Takane, Reo,Ohta, Chiaki,Fujimura, Kazuma,Maegawa, Tomohiro,Miki, Yasuyoshi
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- Synthesis of 3-acylindoles: via copper-mediated oxidative decarbethoxylation of ethyl arylacetates
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An efficient regioselective C-3 acylation of free indoles (N-H) has been accomplished via oxidative decarbethoxylation of easily available ethyl arylacetates using Cu(OAc)2 and KOtBu in DMSO.
- Jaiswal, Anjali,Sharma, Anup Kumar,Singh, Krishna Nand
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supporting information
p. 1623 - 1628
(2020/03/06)
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- Decarboxylative acylation of: N -free indoles enabled by a catalytic amount of copper catalyst and liquid-assisted grinding
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A facile decarboxylative acylation of N-free indoles with α-ketonates via liquid-assisted grinding was reported. The reaction requires only a catalytic amount of Cu(OAc)2·H2O in combination with O2 as the terminal oxidant to give various 3-acylindoles with high efficiency. Additionally, this new methodology was applicable to a gram-scale synthesis.
- Yu, Jingbo,Zhang, Chao,Yang, Xinjie,Su, Weike
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supporting information
p. 4446 - 4451
(2019/05/16)
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- ARYL HYDROCARBON RECEPTOR MODULATORS AND USES THEREOF
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Provided are compounds of Formula (I), and pharmaceutically acceptable salts, solvates, hydrates, stereoisomers, tautomers, isotopically labeled derivatives, polymorphs, and prodrugs thereof, wherein X1-X4, RX, RC, RB, n, and Ring A are as defined herein. The compounds may be aryl hydrocarbon receptor agonists or partial aryl hydrocarbon receptor agonists. Also provided are pharmaceutical compositions comprising a compound of Formula (I) and methods of using such compounds for treating diseases and conditions related to the activity of an aryl hydrocarbon receptor, such as, for example, inflammatory diseases, autoimmune diseases, metabolic disorders, and proliferative diseases.
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Paragraph 00426; 00457
(2019/10/29)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
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supporting information
p. 869 - 872
(2018/02/09)
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- Decarboxylative/decarbonylative C3-acylation of indoles: Via photocatalysis: A simple and efficient route to 3-acylindoles
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A simple and efficient strategy for the preparation of 3-acylindoles via visible-light promoted C3-acylation of free (NH)- and N-substituted indoles with α-oxocarboxylic acids was developed. The reaction tolerates a wide range of functional groups, and the corresponding 3-acylindoles were obtained in high yields under mild conditions.
- Shi, Qing,Li, Pinhua,Zhu, Xianjin,Wang, Lei
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p. 4916 - 4923
(2016/11/04)
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- Hexafluoro-2-propanol-Promoted Intermolecular Friedel-Crafts Acylation Reaction
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The intermolecular Friedel-Crafts acylation was carried out in hexafluoro-2-propanol to yield aryl and heteroaryl ketones at room temperature without any additional reagents.
- Vekariya, Rakesh H.,Aubé, Jeffrey
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supporting information
p. 3534 - 3537
(2016/08/16)
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- Palladium catalyzed addition of arylboronic acid or indole to nitriles: Synthesis of aryl ketones
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Aryl ketones can be synthesized conveniently by a palladium catalyzed addition of arylboronic acid to nitriles in aqueous triflic acid. This catalytic system was extended to the addition of unprotected indoles to nitriles under a slightly modified condition to produce 3-acyl indoles in good yields.
- Das, Tuluma,Chakraborty, Amarnath,Sarkar, Amitabha
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supporting information
p. 7198 - 7202
(2015/01/09)
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- Synthesis of 3-acylindoles via decarboxylative cross-coupling reaction of free (NH) indoles with α-oxocarboxylic acids
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A convenient and general method for acylation of free (NH) indoles via palladium-catalyzed decarboxylative cross-coupling reaction was developed. This process provided a useful method for the preparation of diverse 3-acylindoles in high yields utilizing a reaction with readily accessible reactants under mild conditions.
- Gu, Li-Jun,Liu, Ji-Yan,Zhang, Li-Zhu,Xiong, Yong,Wang, Rui
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- Facile access to 3-acylindoles through palladium-catalyzed addition of indoles to nitriles: The one-pot synthesis of indenoindolones
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A palladium-catalyzed addition of indoles to nitriles, leading to 3-acylindoles, was reported, and the scope of nitriles was investigated. The strategy described provides a more efficient and atom-economical alternative to indenoindolones. It was found that alkenyl, carbonyl, halogen, methoxy, and nitro groups on aryl nitriles, which could offer opportunities for further synthetic transformations, are all compatible with the conditions. N-unprotected indoles with electron-rich groups show excellent reactivity towards this addition reaction. Under the optimized conditions, an array of indenoindolones are obtained in synthetic useful yields from readily available indoles and nitriles in one pot. The results also show that both the electron-poor and electron-rich substituents could be introduced to indoles and nitriles and that the halogen atoms were compatible under the current conditions.
- Ma, Yuanhong,You, Jingsong,Song, Feijie
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supporting information
p. 1189 - 1193
(2013/02/25)
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- A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina
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A simple and efficient 3-acylation of indoles under microwave-heated and solvent-free conditions is developed. This general procedure uses neutral Al2O3 as a new, green and reusable catalyst giving good to high yields within short reaction times. Utilizing such an environmentally- benign methodology, a variety of indoles bearing electron-releasing or electron-withdrawing groups were conveniently acylated.
- Lai, Qiu Yu,Liao, Rong Su,Wu, Shao Yong,Zhang, Jia Xin,Duan, Xin Hong
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p. 4069 - 4076
(2013/12/04)
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- Iron powder promoted regio-selective friedel-crafts acylation of indole under solvent-free conditions
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A facile, efficient and environment-friendly protocol for the regioselective synthesis of 3-acyl indoles has been developed by one-pot catalytic Friedel-Crafts acylation of indole in presence of the iron powder as catalyst under solvent-free conditions at room temperature.
- Zhang, Lirong,Yi, Fengping,Zou, Jianzhong,Qu, Shaoyan
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p. 6117 - 6120
(2013/07/26)
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- Temperature-dependent product selectivity in the Vilsmeier-Haack reaction on bis(phenylhydrazones) of bis(aroylmethyl) sulfides (=1,1'-[thiobis(methylene) ]bis[arylmethanone] bis(2-phenylhydrazones)): Synthesis of 3-aroylindoles (=aryl(1H-indol-3-yl)methanones)
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The bis(phenylhydrazone) of substituted diphenacyl sulfides (=1,1'-[thiobis(methylene)]bis[arylmethanone] bis(2-phenylhydrazones)) 1 underwent a tandem sequence of reactions upon treatment with Vilsmeier reagent, ultimately yielding 3-aroylindoles (=aryl(1H-indol-3-yl)methanones) 3 (Scheme 1 and Table 1). The reaction seems to be product selective depending upon the reaction temperature. Copyright
- Paul, Nidhin,Muthusubramanian, Shanmugam
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p. 452 - 457
(2013/05/22)
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- ZrCl4-mediated regio- and chemoselective friedel-crafts acylation of indole
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An efficient method for regio- and chemoselective Friedel-Crafts acylation of indole using acyl chlorides in the presence of ZrCl4 has been discovered. It minimizes/eliminates common competing reactions that occur due to high and multiatom-nucleophilic character of indole. In this method, a wide range of aroyl, heteroaroyl alkenoyl, and alkanoyl chlorides undergo smooth acylation with various indoles without NH protection and afford 3-acylindoles in good to high yields.
- Guchhait, Sankar K.,Kashyap, Maneesh,Kamble, Harshad
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experimental part
p. 4753 - 4758
(2011/07/08)
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- COMPOUNDS AND METHODS FOR TREATING PROTEIN FOLDING DISORDERS
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The invention is directed to compounds and methods for treating protein folder disorders. In certain embodiments the invention provides compounds and methods for treating neurodegenerative diseases such as Alzheimer's disease, tauopathy, cerebral amyloid angiopathy, Lewy body disease, dementia, Huntington's disease and prion-based spongiform encelopathy. The invention further provides compounds, methods and pharmaceutical compositions for inhibiting tau protein, Aβ protein or α-synuclein protein aggregation.
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Page/Page column 94-95
(2008/12/05)
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- 3-Acylindoles via a one-pot, regioselective Friedel-Crafts reaction
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Within we report a general one-pot high-yielding Friedel-Crafts acylation of indole using acid chlorides and diethylaluminum chloride in gram scale quantities. This general synthesis affords products that are easily isolated and require no complex purification procedures.
- Wynne, James H.,Lloyd, Christopher T.,Jensen, Samuel D.,Boson, Sean,Stalick, Wayne M.
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p. 2277 - 2282
(2007/10/03)
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- 4-(Benzoylindolizinyl)butyric acids; novel nonsteroidal inhibitors of steroid 5α-reductase. III
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A novel series of indolizinebutyric acids with various benzoyl substituents was synthesized to develop nonsteroidal inhibitors of steroid 5α-reductase, and the structure-activity relationships in this series were studied. We previously reported the structure-activity relationships in a series of indolebutyric acids as well as the discovery of the novel nonsteroidal 5α-reductase inhibitor, FK143. We have now made other modifications to this compound to improve in vivo inhibitory activity. By altering the heterocyclic nucleus and changing the benzoyl substituent we have succeeded in identifying the strongly active compound, FK687, (S)-4-[1-[4-[[1-(4-isobutylphenyl)butyl]oxy]benzoyl]indolizin-3-yllbutyric acid, which displays strong in vitro inhibitory activity against the human enzyme and in vivo inhibitory activity against the castrated young rat model. This compound should be a useful agent for the treatment of benign prostatic hyperplasia.
- Sawada,Okada,Kuroda,Watanabe,Sawada,Tanaka
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p. 799 - 813
(2007/10/03)
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- C-attached aminoalkylindoles: Potent cannabinoid mimetics
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Aminoalkylindoles (AAIs) with potent cannabinoid agonist activity have been synthesized where the aminoalkyl chain is attached to the indole ring via a carbon atom of the cyclic amine.
- D'Ambra, Thomas E.,Eissenstat, Michael A.,Abt, Jeffrey,Ackerman, James H.,Bacon, Edward R.,Bell, Malcolm R.,Carabateas, Philip M.,Josef, Kurt A.,Kumar, Virendra,Weaver III, John D.,Arnold, Renee,Casiano, Frances M.,Chippari, Susan M.,Haycock, Dean A.,Kuster, Joan E.,Luttinger, Daniel A.,Stevenson, Joan I.,Ward, Susan J.,Hill, W. Adam,Khanolkar, Atmaram,Makriyannis, Alexandros
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- INDOLE DERIVATIVES AND THEIR USE FOR TESTOSTERONE 5-ALPHA-REDUCTASE-MEDIATED DISEASES
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Indole derivatives of the formula and pharmaceutical compositions thereof. They are useful for treating or preventing testosterone 5-alpha-reductase-mediated diseases, such as alopecia, acnes and prostatism
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- Antinociceptive (Aminoalkyl)indoles
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The (aminoalkyl)indole (AAI) derivative pravadoline (1a) inhibited prostaglandin (PG) synthesis in mouse brain microsomes in vitro and ex vivo and exhibited antinociceptive activity in several rodent assays.In vitro structure-activity relationship studies of this new class of PG synthesis inhibitors revealed a correspondence in three respects to those reported for the arylacetic acids: (1) "α-methylation" caused an increase in PG inhibitory potency, (2) the (R)-α-methyl isomer was more active than the S isomer, (3) the hypothesized aroyl group conformation of the 2-methyl derivatives corresponded to the proposed and reported "active" conformations of the aroyl and related aromatic acetic acid derivatives.The 1H NMR chemical shift of the C-4 hydrogen of pravadoline in comparison to the deshielding seen with 50, which lacks a substituent at C-2, suggested that the carbonyl group of pravadoline is located near C-2 but is located near C-4 in 50.Associated with this conformational change of the carbonyl group of 1a is a diminution of PG synthetase inhibitory activity.The results of UV and difference nuclear Overhauser studies of the two compounds were consistent with these conformational assignments.The low eudismic ratios of the α-methyl derivatives and the observation that the side chain may be extended by three methylene groups without significant loss of PG inhibitory potency suggests that this class of inhibitors bound less strongly and less selectively to the active site of PG synthetase than do the arylacetic acids.Two AAIs, 1a and 30, were found to be metabolized to the corresponding acetic acid derivatives, both of which inhibited PG synthesis.An exception to the observation that the antinociceptive activity of the AAIs was associated with PG synthetase inhibitory activity was the 1-naphthoyl derivative 67 since neither it nor its acetic acid metabolite 74 inhibited PG synthesis.Yet 67 was antinociceptive in four different rodent assays.This naphthoyl derivative, like opioids, also inhibited electrically stimulated contractions in the mouse vas deferens (MVD) preparation.Unlike opioids, however, the inhibition was not antagonized by naloxone.A subseries of AAIs was identified, of which 67 was prototypic.These compounds lacked PG synthetase inhibitory activity, but their inhibitory potency in MVD preparations correlated roughly with their antinociceptive potency in vivo.Pravadoline was also inhibitory in MVD.Is antinociceptive activity, therefore, may be a consequence of both its PG synthease inhibitory potency and another antinociceptive mechanism, the latter associated with its inhibitory potency in the MVD.The evidence is summarized which suggests that this second antinociceptive mechanism is associated with binding to the recently characterized cannabinoid receptor.
- Bell, Malcolm R.,D'Ambra, Thomas E.,Kumar, Virendra,Eissenstat, Michael A.,Herrmann, John L.,et al.
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p. 1099 - 1110
(2007/10/02)
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- Acylindole derivatives and their use in pharmaceutical compositions
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The present invention is concerned with novel acylindole derivatives of the formula (I) and platelet-aggregation inhibiting agents containing them as an active ingredient. STR1 In the formula (I), either R1 and R2 is hydrogen, an alk
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