- The total synthesis of (?)-indolactam I
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The first total synthesis of (?)-indolactam I (1) is reported. An efficient synthetic route was established to furnish the natural product in 8 steps. This strategy employed a copper-catalyzed amino acid arylation, peptide coupling, and Lewis acid-mediate
- Mendoza, Manuel,Rao, Niveda,Tran, UyenPhuong,Castaneda, Catherine,Billingsley, Kelvin L.
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Read Online
- COMPOUNDS AND USES THEREOF
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The present disclosure features compounds useful for the treatment of BAF complex-related disorders.
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Page/Page column 71; 106
(2021/08/06)
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- Rhodium(II)-Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)-Aurantioclavine
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An efficient rhodium(II)-catalyzed [4+3] cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed. Azepino[5,4,3- cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good
- Duan, Shengguo,Xue, Bing,Meng, Hui,Ye, Zihang,Xu, Ze-Feng,Li, Chuan-Ying
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supporting information
p. 1145 - 1152
(2021/04/26)
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- Iodine-Mediated Electrochemical C(sp2)-H Amination: Switchable Synthesis of Indolines and Indoles
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A metal-free electrochemical intramolecular C(sp2)-H amination using iodine as a mediator was developed. This method enables a switchable synthesis of indoline and indole derivatives, respectively, from easily available 2-vinyl anilines.
- Hu, Kangfei,Zhang, Yan,Zhou, Zhenghong,Yang, Yu,Zha, Zhenggen,Wang, Zhiyong
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supporting information
p. 5773 - 5777
(2020/08/05)
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- The Synthesis and Biological Evaluation of Indolactam Alkaloids
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In this work, we execute a general synthetic strategy to access novel indolactam alkaloids, which are agonists of protein kinase C. This protocol allowed for the most efficient reported syntheses of indolactam V (ILV) stereoisomers, while also affording t
- Billingsley, Kelvin L.,Eom, Ryan,Haynes-Smith, Jeremy,Mendoza, Manuel,Salas, Celeste
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p. 4443 - 4451
(2019/11/21)
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- ISOXAZOLE DERIVATIVE AS MUTATED ISOCITRATE DEHYDROGENASE 1 INHIBITOR
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It has been found that a compound of the general formula (I) having an isoxazole skeleton has excellent inhibitory activity against mutant IDH1 protein and inhibits the production of 2-HG by this protein, while the compound is also capable of effectively inhibiting the growth of various tumors expressing the protein. In the formula, R1, R2, R3, Y, and Z are as defined in claim 1.
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Paragraph 0305; 0306
(2018/02/06)
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- Modular Total Synthesis of Protein Kinase C Activator (-)-Indolactam v
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A concise, eight-step total synthesis of (-)-indolactam V, a nanomolar agonist of protein kinase C, is reported. The synthesis relies upon an efficient copper-catalyzed amino acid arylation to establish the indole C4-nitrogen bond. This cross-coupling met
- Haynes-Smith, Jeremy,Diaz, Italia,Billingsley, Kelvin L.
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supporting information
p. 2008 - 2011
(2016/06/01)
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- Preparation of No-Carrier-Added 6-[18F]Fluoro-l-tryptophan via Cu-Mediated Radiofluorination
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18F-Labeled aromatic amino acids exhibit great potential for diagnostic applications using positron emission tomography. However, the introduction of18F into aromatic compounds remains challenging, and novel fluorination methods facilitating easy access to18F-labeled arenes are highly sought after. In recent years, novel metal-mediated fluorination methods have been reported and transferred into radiochemistry. Based on Cu-mediated radiofluorination, a two-step synthesis of no-carrier-added (n.c.a.) 6-[18F]fluoro-l-tryptophan was developed. 6-[18F]Fluoro-l-tryptophan was synthesized with an overall radochemical yield of 16 ± 4% within 110 min and a specific activity of 280 GBq μmol–1. The radiochemical purity was more than 99 %. The developed method allowed access to radiofluorinated tryptophan derivatives in high radiochemical yields and opens new ways to provide radiofluorinated amino acids. Furthermore, the reaction conditions were optimized to facilitate automation.
- Sch?fer, Dominique,Wei?, Philipp,Ermert, Johannes,Castillo Meleán, Johnny,Zarrad, Fadi,Neumaier, Bernd
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p. 4621 - 4628
(2016/09/28)
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- Room-Temperature Gold-Catalysed Arylation of Heteroarenes: Complementarity to Palladium Catalysis
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Tailoring of the pre-catalyst, the oxidant and the arylsilane enables the first room-temperature, gold-catalysed, innate C?H arylation of heteroarenes. Regioselectivity is consistently high and, in some cases, distinct from that reported with palladium ca
- Cresswell, Alexander J.,Lloyd-Jones, Guy C.
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supporting information
p. 12641 - 12645
(2016/08/30)
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- Novel Aza-analogous ergoline derived scaffolds as potent serotonin 5-HT6 and dopamine D2 receptor ligands.
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By introducing distal substituents on a tetracyclic scaffold resembling the ergoline structure, two series of analogues were achieved exhibiting subnanomolar receptor binding affinities for the dopamine D2 and serotonin 5-HT6 receptor subtype, respectively. While the 5-HT 6 ligands were antagonists, the D2 ligands displayed intrinsic activities ranging from full agonism to partial agonism with low intrinsic activity. These structures could potentially be interesting for treatment of neurological diseases such as schizophrenia, Parkinson's disease, and cognitive deficits.
- Krogsgaard-Larsen, Niels,Jensen, Anders A.,Schr?der, Tenna J.,Christoffersen, Claus. T.,Kehler, Jan
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supporting information
p. 5823 - 5828
(2014/08/05)
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- Syntheses of aza-analogous iso-ergoline scaffolds using carbene mediated C-H insertion
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A novel direct, flexible, and robust approach to the iso-ergoline tetracyclic system in which a five or six-membered ring is established by intramolecular carbene C-H insertion is reported. The protocol involves a two step conversion of an aromatic aldehyde to the corresponding hydrazone and without purification further conversion to the diazo-compound followed by thermal carbene formation and C-H insertion α to a nitrogen.
- Krogsgaard-Larsen, Niels,Begtrup, Mikael,Frydenvang, Karla,Kehler, Jan
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experimental part
p. 9297 - 9303
(2011/01/12)
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- COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
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Provided herein are compounds and methods of synthesis thereof. The compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, psychiatric disorders, neuromuscular disorders, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds provided herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
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Page/Page column 216-217
(2010/11/03)
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- Enantioselective organo-SOMO cascade cycloadditions: A rapid approach to molecular complexity from simple aldehydes and olefins
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A highly selective, radical-mediated (4 + 2) coupling reaction of aldehydes and conjugated olefins has been achieved through asymmetric SOMO-catalysis. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnishes a cation which is vulnerable to nucleophilic addition. A range of aromatic aldehydes are shown to couple with styrenes and dienes to provide cyclic products with high chemical efficiency, regioselectivity, and stereoselectivity.
- Jui, Nathan T.,Lee, Esther C. Y.,MacMillan, David W. C.
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supporting information; experimental part
p. 10015 - 10017
(2010/10/03)
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- INDOLES AS 5-HT6 MODULATORS
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The present invention relates to novel compounds of formula (I) wherein m, n, R0, R1, R2, R3 and R4 are as described herein, to pharmaceutical compositions comprising the compounds, to processes for t
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Page/Page column 65
(2008/06/13)
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- Towards the syntheses of N-H and N-alkylated derivatives of meridianins
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(Chemical Equation Presented) Novel N-H and N-alkylated derivatives of meridianins have been synthesized as potential antitumor agents by a two-step conversion of N-tosyl-3-acetylindoles or N-alkyl-3-acetylindoles to the corresponding enaminones using DMF-DMA, with or without added pyrrolidine. Further cyclization with guanidine gave the corresponding 2-aminopyrimidines. The structures of the compounds, thus obtained, were proved by 1H and 13C NMR spectroscopy, NOE experiments and X-ray analysis.
- Simon, Ga?lle,Couthon-Gourves, Hélène,Haelters, Jean-Pierre,Corbel, Bernard,Kervarec, Nelly,Michaud, Fran?ois,Meijer, Laurent
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p. 793 - 801
(2008/03/29)
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- Novel entry to the Ergot alkaloids via ring closing metathesis
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A novel entry the Ergot alkaloids has been developed. It features a Heck reaction followed by hydride capture to generate the key tricyclic intermediate 12 and a ring closing metathesis reaction to give the tetracyclic ergoline ring system 3.
- Lee, Katherine L.,Goh, Jane Betty,Martin, Stephen F.
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p. 1635 - 1638
(2007/10/03)
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- Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles
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4-Bromo-1-tosylindole (1) was converted to tricyclic indole enone 11, a potential intermediate in the synthesis of tetracyclic ergot alkaloids, by a series of palladium-catalyzed processes.Attempts to construct the ergot D ring by the hetero-Diels-Alder reaction of enone 11 and 1-azabutadiene 12 produced not the expected adduct 13 but the benzindoline derivative 14 resulting from attack of the aza diene at the indole 2-position.The thermodynamic stability of the naphthol nucleus makes enone 11 generally susceptible to attack at the indole 2-position,as evidenced by the attack of hydride and methyl cuprate nucleophiles at this position forming indolines 16 and 17, respectively.
- Hegedus, Louis S.,Sestrick, Michael R.,Michaelson, Eric T.,Harrington, Peter J.
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p. 4141 - 4146
(2007/10/02)
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- A FACILE ONE STEP SYNTHESIS OF 4-AMINOINDOLES FROM 5-HALO-4-OXO-4,5,6,7-TETRAHYDROINDOLES
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Reaction of 5-halo-4-oxo-4,5,6,7-tetrahydroindoles with amines initiates the amination of the carbonyl function and ensuing dehydrohalogenation leads to a successful formation of 4-aminoindoles.
- Matsumoto, Masakatsu,Ishida, Yasuko,Hatanaka, Naoto
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p. 1667 - 1674
(2007/10/02)
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- Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. Approaches to Ergot Alkaloids
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An efficient synthesis of 4-bromo-1-tosylindole (10) based on the Pd(II)-catalyzed cyclization of an o-ethenylaniline p-toluenesulfonamide has been developed.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted 10 to a number of 4-substituted 1-tosylindoles.Selective electrophilic substitutions at the 3-position of 10 provided access to the 3-(chloromercurio)- (18) and 3-iodo-1-tosylindoles (22).Transmetalation to palladium and allyl chloride insertion converted 18 to 3-allyl-4-bromo-1-tosylindole (20) which could be cyclized to the benzindoline 21.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted the 3-iodo compound 22 to a number of 4-bromo-3-substituted 1-tosylindoles including 24, a potential precursor to optically active tryptophans.
- Harrington, Peter J.,Hegedus, Louis S.
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p. 2658 - 2662
(2007/10/02)
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