1463045-57-9Relevant academic research and scientific papers
Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-b]indole Core. Unusual Fragmentation with 1,2-Aryl Shift
Aksenov, Alexander V.,Aksenov, Dmitrii A.,Aksenov, Nicolai A.,Aksenova, Anna A.,Aleksandrova, Elena V.,Nobi, Mezvah A.,Rubin, Michael
, p. 1434 - 1444 (2022/01/27)
Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for N-alkyl derivatives of oxoindolines took the expected route by only providing 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles.
FeCl3-Catalyzed Allylation Reactions onto 3-Hydroxy-2-oxindoles: Formal Total Syntheses of Bis-cyclotryptamine Alkaloids, (±)-Chimonanthine, and (±)-Folicanthine
Kinthada, Lakshmana K.,Medisetty, Sai Raghavendra,Parida, Amarchand,Babu, K. Naresh,Bisai, Alakesh
, p. 8548 - 8567 (2017/08/23)
An FeCl3-catalyzed efficient strategy for the allylation reactions of 3-hydroxy-2-oxindoles with allyltrimethylsilane has been developed. The reaction affords a variety of 2-oxindoles having quaternary center at the pseudobenzylic position in an operationally simple and inexpensive procedure. Control experiments using enantioenriched 3-hydroxy-2-oxindole show that the reaction proceeds through in situ generated 2H-indol-2-one (8). The methodology presents an efficient and concise access to the pyrroloindoline alkaloids (±)-deoxyeseroline (1a), (±)-esermethole (1b), (±)-physostigmine (1c), (±)-phenserine (1d), and (±)-physovenine (1e). Eventually, we extrapolated the scope of this methodology to the formal total syntheses of dimeric cyclotyrptamine alkaloids (±)-chimonanthine (3a), (±)-folicanthine (3c), and (±)-calycanthine (4).
Highly chemoselective synthesis of dimeric 2-oxindoles with a C-3/C-5′ linkage via Friedel-Crafts alkylations of 2-oxindoles with 3-hydroxy-2-oxindoles
Babu, K. Naresh,Kinthada, Lakshmana K.,Ghosh, Santanu,Bisai, Alakesh
, p. 10641 - 10655 (2015/11/17)
Simple and convenient Lewis acid-catalyzed Friedel-Crafts alkylations of 2-oxindoles as electron rich aromatics with 3-hydroxy-2-oxindoles as electron deficient partners have been developed. The reaction afforded a variety of dimeric 2-oxindoles with a C-
3-3-DI-SUBSTITUTED-OXINDOLES AS INHIBITORS OF TRANSLATION INITIATION
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Page/Page column 65, (2014/04/04)
Compositions and methods for inhibiting translation are provided. Compositions, methods and kits for treating (1) cellular proliferative disorders, (2) non-proliferative, degenerative disorders, (3) viral infections, and/or (4) disorders associated with viral infections, using diaryloxindole compounds are described.
Acid-catalyzed reactions of 3-hydroxy-2-oxindoles with electron-rich substrates: Synthesis of 2-oxindoles with all-carbon quaternary center
Kinthada, Lakshmana K.,Ghosh, Santanu,De, Subhadip,Bhunia, Subhajit,Dey, Dhananjay,Bisai, Alakesh
, p. 6984 - 6993 (2013/10/08)
A Lewis acid catalyzed reaction of in situ generated 2H-indol-2-one (9) with various 2π and other electron-rich substrates has been developed. A variety of electron-rich substrates such as allyl/methallyltrimethylsilane, phenylacetylene, styrenes, acetophenone, and indoles have been used. The methodology provides a straightforward approach for the synthesis of 2-oxindoles with an all-carbon quaternary center at the pseudobenzylic position.
Synthesis and SAR study of novel 3,3-diphenyl-1,3-dihydroindol-2-one derivatives as potent eIF2·GTP·Met-tRNAiMet ternary complex inhibitors
Denoyelle, Séverine,Chen, Ting,Yang, Hongwei,Chen, Limo,Zhang, Yingzhen,Halperin, José A.,Aktas, Bertal H.,Chorev, Michael
, p. 537 - 553 (2013/10/22)
The growing recognition of inhibition of translation initiation as a new and promising paradigm for mechanism-based anti-cancer therapeutics is driving the development of potent, specific, and druggable inhibitors. The 3,3-diaryloxindoles were recently reported as potential inhibitors of the eIF2·GTP·Met-tRNAiMet ternary complex assembly and 3-{5-tert-butyl-2-hydroxyphenyl}-3-phenyl-1,3-dihydro-2H-indol-2- one #1181 was identified as the prototypic agent of this chemotype. Herein, we report our continuous effort to further develop this chemotype by exploring the structural latitude toward different polar and hydrophobic substitutions. Many of the novel compounds are more potent than the parent compound in the dual luciferase ternary complex reporter assay, activate downstream effectors of reduced ternary complex abundance, and inhibit cancer cell proliferation in the low μM range. Moreover, some of these compounds are decorated with substituents that are known to endow favorable physicochemical properties and as such are good candidates for evaluation in animal models of human cancer.
