94964-56-4Relevant academic research and scientific papers
Oxidative Dearomatization of 4,5,6,7-Tetrahydro-1H-indoles Obtained by Metal- and Solvent-Free Thermal 5-endo-dig Cyclization: The Route to Erythrina and Lycorine Alkaloids
Andreev, Ivan A.,Ratmanova, Nina K.,Novoselov, Anton M.,Belov, Dmitry S.,Seregina, Irina F.,Kurkin, Alexander V.
supporting information, p. 7262 - 7267 (2016/05/19)
A facile one-pot approach based on a thermally induced metal- and solvent-free 5-endo-dig cyclization reaction of the amino propargylic alcohols in combination with Dess-Martin periodinane-promoted oxidative dearomatization of 4,5,6,7-tetrahydroindole intermediates provides an efficient and robust access to 5,6-dihydro-1H-indol-2(4H)ones. Green, relatively mild and operationally simple characteristics of the synthetic sequence are the major advantages, which greatly amplify the developed methodology. The utility of obtained indolones as unified key precursors is demonstrated by the application of these products to the formal total syntheses of a whole pleiad of Erythrina- and Lycorine-type alkaloids, namely (±)-erysotramidine, (±)-erysotrine, (±)-erythravine, (±)-γ-lycorane, and abnormal erythrinanes (±)-coccoline and (±)-coccuvinine.
Discovery of the 2-phenyl-4,5,6,7-Tetrahydro-1 H -indole as a novel anti-hepatitis C virus targeting scaffold
Andreev, Ivan A.,Manvar, Dinesh,Barreca, Maria Letizia,Belov, Dmitry S.,Basu, Amartya,Sweeney, Noreena L.,Ratmanova, Nina K.,Lukyanenko, Evgeny R.,Manfroni, Giuseppe,Cecchetti, Violetta,Frick, David N.,Altieri, Andrea,Kaushik-Basu, Neerja,Kurkin, Alexander V.
supporting information, p. 250 - 258 (2015/04/27)
Although all-oral direct-acting antiviral (DAA) therapy for hepatitis C virus (HCV) treatment is now a reality, today's HCV drugs are expensive, and more affordable drugs are still urgently needed. In this work, we report the identification of the 2-phenyl-4,5,6,7-Tetrahydro-1H-indole chemical scaffold that inhibits cellular replication of HCV genotype 1b and 2a subgenomic replicons. The anti-HCV genotype 1b and 2a profiling and effects on cell viability of a selected representative set of derivatives as well as their chemical synthesis are described herein. The most potent compound 39 displayed EC50 values of 7.9 and 2.6 μM in genotype 1b and 2a, respectively. Biochemical assays showed that derivative 39 had no effect on HCV NS5B polymerase, NS3 helicase, IRES mediated translation and selected host factors. Thus, future work will involve both the chemical optimization and target identification of 2-phenyl-4,5,6,7-Tetrahydro-1H-indoles as new anti-HCV agents.
Synthesis of 4,5,6,7-tetrahydro-1H-indole derivatives through successive sonogashira coupling/Pd-mediated 5-endo-dig cyclization
Andreev, Ivan A.,Belov, Dmitry S.,Kurkin, Alexander V.,Yurovskaya, Marina A.
supporting information, p. 649 - 652 (2013/03/13)
A one-pot Sonogashira cross-coupling/5-endo-dig cyclization procedure leading to 2-aryl-4,5,6,7-tetrahydroindoles was developed. This short (only two steps from commercially available compounds) sequence avoids harsh conditions and expensive catalysts. Our procedure is highly tolerant to a range of functional groups (amino, nitro, carboxy, cyano, hydroxy, and bromo). A family of 21 tetrahydroindoles was synthesized on a gram scale in a good to excellent yields, which is indicative of the general character and scalability of this reaction. This methodology allows access to indoles bearing miscellaneous substituents at the C2 position (by variation of ArI) and at the nitrogen atom (by variation of RNH2, including chiral moieties). A one-pot sequence based on Sonogashira cross-coupling/Pd-mediated 5-endo-dig cyclization was developed and applied to the gram-scale synthesis of 2-aryl-4,5,6,7- tetrahydroindoles (21 examples). Copyright
Highly stereoselective and scalable synthesis of trans -fused octahydrocyclohepta[ b ]pyrrol-4(1 H)-ones via the aza-Cope-Mannich rearrangement in racemic and enantiopure forms
Belov, Dmitry S.,Lukyanenko, Evgeny R.,Kurkin, Alexander V.,Yurovskaya, Marina A.
, p. 10125 - 10134 (2013/01/15)
We have developed an efficient and stereoselective route to trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones. The key features of our synthesis include the regioselective epoxide ring-opening of alkynyl oxiranes and a stereoselective aza-Cope-Mannich r
Synthesis of (3RS,3aSR,8aSR)-3-phenyloctahydrocyclohepta[b]pyrrol-4(1H)-one via the aza-Cope-Mannich rearrangement
Belov, Dmitry S.,Lukyanenko, Evgeny R.,Kurkin, Alexander V.,Yurovskaya, Marina A.
scheme or table, p. 9214 - 9218 (2011/12/01)
A convenient and scalable method for the preparation of (3RS,3aSR,8aSR)-phenyloctahydrocyclohepta[b]pyrrol-4(1H)-one based on the aza-Cope-Mannich rearrangement is described. This approach allows us to synthesize the target compound in nine steps in a high overall yield (42%) with complete stereocontrol and up to 100 g scale.
