58550-84-8Relevant academic research and scientific papers
Construction of pyrrole- and indole-fused CF3-piperazine derivatives
Tian, Yu-Ting,Zong, Yu-Wei,Nie, Jing,Zhang, Fa-Guang,Ma, Jun-An
, (2019/09/03)
A series of pyrrole- and indole-fused trifluoromethyl-functionalized piperazine derivatives were constructed in moderate to good yields with excellent chemoselectivities via a Pictet-Spengler reaction under mild and operationally simple conditions. The synthetic utility of this protocol was further extended by the facile preparation of indole-fused CF3-1,4-diazocane and enantioenriched CF3-piperazines via a vinylogous Pictet-Spengler reaction and an asymmetric Pictet-Spengler reaction, respectively.
Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate
Ding, Lu,Gao, Run-Duo,You, Shu-Li
supporting information, p. 4330 - 4334 (2019/02/25)
An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71–86 %) with excellent enantioselectivity (91–96 % ee) and chemoselectivity (3/4>19:1 in most cases).
Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators
Greig, Iain R.,Baillie, Gemma L.,Abdelrahman, Mostafa,Trembleau, Laurent,Ross, Ruth A.
, p. 4403 - 4407 (2016/08/25)
Existing CB1 negative allosteric modulators (NAMs) fall into a limited range of structural classes. In spite of the theoretical potential of CB1 NAMs, published in vivo studies have generally not been able to demonstrate the expected therapeutically-relevant CB1-mediated effects. Thus, a greater range of molecular tools are required to allow definitive elucidation of the effects of CB1 allosteric modulation. In this study, we show a novel series of indole sulfonamides. Compounds 5e and 6c (ABD1075) had potencies of 4 and 3?nM respectively, and showed good oral exposure and CNS penetration, making them highly versatile tools for investigating the therapeutic potential of allosteric modulation of the cannabinoid system.
Synthesis and Diels-Alder reactions of pyrrolo[3,4-b]indoles. A synthesis of 4-acetamidocarbazoles and an approach to the antiostatins
Pelkey, Erin T.,Jiang, Jun,Gribble, Gordon W.
, p. 1525 - 1536 (2014/01/17)
The Diels-Alder reaction of N-acetylpyrrolo[3,4-b]indoles with 4-acetamidocarbazoles affords cycloadducts that undergo ring opening with catalytic p-toluenesulfonic acid to give 4-aminocarbazoles. Application of this strategy to the synthesis of naturally occurring 4-amidocarbazole antiostatins has not been achieved.
N- (ARYLALKYL) - 1H- INDOLE- 2 - SULFONIC ACID AMIDE COMPOUNDS AND THEIR THERAPEUTIC USE AS CANNABINOID ALLOSTERIC MODULATORS
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Page/Page column 99, (2012/09/21)
The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain /V-(arylalkyl)-1 H-indole- 2-sulfonic acid amide compounds that, inter alia, inhibit cannabinoid receptor signalling. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit cannabinoid receptor signalling; to treat disorders that are ameliorated by the inhibition of cannabinoid receptor signalling; to treat metabolic syndrome, type-2 diabetes, dyslipidaemia, obesity, eating disorders, cardiovascular diseases and disorders, and other conditions as described herein.
A novel approach to 3-methylindoles by a heck/cyclization/isomerization process
Baxter, Carl A.,Cleator, Ed,Alam, Mahbub,Davies, Antony J.,Goodyear, Adrian,o'Hagan, Michael
supporting information; experimental part, p. 668 - 671 (2010/04/02)
Chemical Equation presented A novel synthesis of 3-methyllndoles from chlorotrlflates through a Heck reaction, carbamate/aryl chloride coupling, and Isomerlzatlon sequence Is presented. The three-step sequence Is highly efficient and general, enabling the
Pyridinophanes as two-centre phase-transfer catalyst for N-alkylation reaction
Rajakumar, Perumal,Dhanasekaran, Manickam
, p. 654 - 658 (2007/10/03)
The synthetic utility of water-soluble pyridinophanes 1 and 2 as an efficient two-centre phase-transfer catalyst for N-alkylation of indoles, imidazole, benzimidazole and benzotriazole has been explored. Application of such pyridinophanes for the synthesis of various precyclophanes involving bis-N alkylation is also described. Georg Thieme Verlag Stuttgart.
A convenient synthesis of 2-cyano-3-substituted indoles
Denison, Sophie,Hilton, Stephen T.
, p. 2806 - 2808 (2007/10/03)
A new and mild method for the synthesis of 2-cyano-3-substituted indoles is described which is effective on N-unsubstituted indoles.
Nucleophilic addition reactions of 2-nitro-1-(phenylsulfonyl)indole. A new synthesis of 3-substituted-2-nitroindoles
Pelkey, Erin T.,Barden, Timothy C.,Gribble, Gordon W.
, p. 7615 - 7619 (2007/10/03)
2-Nitro-1-(phenylsulfonyl)indole (1) undergoes nucleophilic addition reactions with the enolates of diethyl malonate and cyclohexanone, lithium dimethylcuprate, and indole anion to afford the corresponding 3-substituted-2-nitroindoles (4-6,8,9) in low to high yields. Reaction of 1-(phenylsulfonyl)-2-(trialkylstannyl)indoles 13 and 14 with tetranitromethane affords the novel isoxazolo[5,4-b]indole 15 via a 1,3-dipolar cycloaddition reaction with in situ generated nitro formonitrile oxide (19).
Heteroaromatic diphosphines as chiral ligands
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, (2008/06/13)
Chiral diphosphines constituted by an aromatic pentatomic biheterocyclic system, suitable to act as chiral ligands, complexes between said diphosophines and transition metals, and their utilization as chiral catalysts in sterocontrolled reactions, such as diastereo- and enantioselective reduction reactions. Process for the preparation of said chiral diphosophines and process for the preparation of said complexes and for their utilization as chiral catalysts in sterocontrolled reactions.
