1354630-82-2Relevant academic research and scientific papers
Synthesis of indolyl pyrazole scaffolds as potential anti-cancer agents and their molecular modelling studies
Gaddam, Ganga Reddy,Dubey, Pramod Kumar,Chittireddy, Venkata Ramana Reddy
, p. 828 - 839 (2020/07/10)
Background: Indole and pyrazoles are one of the prime structural units in the field of medicinal chemistry and have been reported to exhibit a variety of biological activities specifically anti-cancer. In view of their medicinal significance, we synthesized a conjugate of the two moieties to get access to newer and potential anti-cancer agents. Methods: Indolyl pyrazoles [3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-(1-methyl-1H-indole-3-carbon yl)acrylonitriles] (4a-l) were synthesized by adopting simple and greener protocol and all the synthesized derivatives were docked against Bcl-2 protein and the selected chemical moieties were screened for their cytotoxicity by using the MTT assay. Results: All the synthesized compounds were docked against BCL-2 protein in order to understand their binding pattern. Among the 12 compounds docked, 4d, 4f, 4h, 4j, and 4l compounds exhibited better protein binding interactions and the same were screened for their anti-cancer activity against A549 (lung) cancer cell lines at a concentration of 100 μM using Doxorubicin as standard. Substitutions such as N-benzyl, N-ethyl groups and halogen groups such as Br, Cl on indole ring showed moderate activity against A-549 cell lines. Conclusion: Among the 5 indolyl pyrazole derivatives screened, compounds 4h and 4j showed significantly better activity with an IC50 of 33.12 and 34.24 μM, respectively. Further, structural tweaking of the synthesized new chemical entities may lead to potential hit/lead-like molecules.
Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence
Adepu, Raju,Dhanaji, Jadhav Rahul,Samatha, Polasani,Mainkar, Prathama S.,Chandrasekhar, Srivari
supporting information, p. 8224 - 8228 (2020/11/18)
A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
EPAC1 ACTIVATORS AS HIV LATENCY REVERSAL AGENTS (LRA)
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, (2019/04/14)
The invention relates generally to novel EPAC1 activators, such as Formula I and the preparation thereof as well as the use of EPAC1 activators as human immunodeficiency virus (HIV) latency reversal agents (LRAs).
Design, synthesis and crystallographic study of novel indole-based cyano derivatives as key building blocks for heteropolycyclic compounds of major complexity
García, Andrés C.,Abonía, Rodrigo,Jaramillo-Gómez, Luz M.,Cobo, Justo,Glidewell, Christopher
, p. 1040 - 1049 (2017/12/12)
A four-stage reaction sequence has been designed and developed for the synthesis of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds of potential pharmaceutical value. The sequence starts with simple commercially available indoles and proceeds via 3-(indol-3-yl)-3-oxopropanenitriles, which react with 2-bromobenzaldehyde to form the corresponding chalcones; these are readily reduced to dihydrochalcones, which are in turn acylated to form the enolate esters. The compounds in this sequence have been characterized by IR and 1H and 13C NMR spectroscopy, by mass spectrometry and by elemental analysis. The molecular and supramolecular structures are reported for representative examples, namely (E)-3-(2-bromophenyl)-2-(1-methyl-1H-indole-3-carbonyl)acrylonitrile, C19H13BrN2O, (Ib), (2RS)-2-(2-bromobenzyl)-3-(1-methyl-1H-indol-3-yl)-3-oxopropanenitrile, C19H15BrN2O, (IIb), and (2RS)-3-(1-benzyl-1H-indol-3-yl)-2-(2-bromobenzyl)-3-oxopropanenitrile, C25H19BrN2O, (IIc), the latter two of which crystallize with Z′ = 2, and (E)-1-(1-acetyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl acetate, C22H17BrN2O, (III), and (E)-1-(1-benzyl-1H-indol-3-yl)-3-(2-bromophenyl)-2-cyanoprop-1-en-1-yl benzoate, C32H23BrN2O, (IV). The structure of the related chalcone (E)-2-benzoyl-3-(2-bromophenyl)prop-2-enenitrile, (V), has been redetermined at 100 K, where it is monoclinic, as opposed to the triclinic form reported at ambient temperature.Crystal structures have been determined for representative compounds along a four-stage synthetic sequence newly developed for the production from simple indoles of highly functionalized enolate esters as key building blocks for the synthesis of novel heteropolycyclic compounds.
N-Bromosuccinimide (NBS)-Catalyzed C-H Bond Functionalization: An Annulation of Alkynes with Electron Withdrawing Group (EWG)-Substituted Acetyl Indoles for the Synthesis of Carbazoles
Wang, Han,Wang, Zhen,Wang, Yi-Long,Zhou, Rui-Rui,Wu, Guang-Chuan,Yin, Si-Yao,Yan, Xu,Wang, Bin
supporting information, p. 6140 - 6143 (2017/11/24)
An N-bromosuccinimide-catalyzed intermolecular annulation of acetyl indoles with alkynes was developed, allowing for regioselective formation of valuable carbazoles through direct C-H bond functionalization. The readily available catalyst, wide substrate scope, gram scale synthesis, and mild conditions make this method practical. Mechanistic investigations indicate that the bromination of acetyl indole takes place to generate a bromide intermediate, followed by coupling with an alkyne and intramolecular cycloaromatization to furnish carbazole products.
