Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts DOI Open Access

Chang‐Rui Nie,

Mingyao Pan,

Rong Deng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Abstract We describe a selective preparation of variety functionalized pyrrolo[2,3‐ c ]tetrahydroquinolines and indolo[3,2‐ in 40–82% 40–80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N ‐arylation, intramolecular [3+2] cycloaddition, [1.3] or [3,3]‐rearrangement N−O bond total three steps. Experimental studies revealed that EtOAc solvent copper(II)‐catalyst played crucial roles on the formation these two tetrahydroquinoline scaffolds. Moreover, scaffolds could be converted into various building blocks by further transformations.

Language: Английский

Biochemical and Computational Insights into the Therapeutic Potencies of Quinoline Appended Imidazole Compounds DOI
Nagarjuna Prakash Dalbanjan, Lokesh Bheemayya,

Karuna Korgaonkar

et al.

ChemistrySelect, Journal Year: 2025, Volume and Issue: 10(14)

Published: April 1, 2025

Abstract Diabetes is a complex metabolic disorder characterized by oxidative stress and chronic inflammation, necessitating the development of multifunctional therapeutic agents. This study evaluates in vitro silico antihyperglycemic, antioxidant, anti‐inflammatory activities four 3‐(4,5‐diaryl‐1 H ‐imidazol‐2‐yl)quinoline‐2‐amine derivatives (a–d) . Among them, compound (a) exhibited strong antihyperglycemic activity, with significant α‐amylase inhibition (IC 50 = 132.55 ± 4.12 µg/mL) enhanced glucose uptake yeast cells 126.32 3.48 µg/mL). Compound (d) showed superior antioxidant 42–44 properties. Molecular docking against PPAR‐γ confirmed binding interactions for all compounds, showing collectively better affinity (−10 kcal/mol −11.1 kcal/mol). Further, molecular dynamics normal mode analysis validated its stability functional potential. The ADMET predictions suggested favorable pharmacokinetics, especially compounds (b) findings suggest that has potential as lead molecule treatment moderate also shows promise, albeit slightly lower bioactivity. Despite these promising findings, none tested outperformed efficacy standard drugs any assays, indicating need further structural optimization to enhance their

Language: Английский

Citations

0
In-vitro and in-silico pharmacological profiling of 3-(4,5-diaryl-1H-imidazol-2-yl)quinoline-2-amine hybrids DOI Creative Commons
Nagarjuna Prakash Dalbanjan, Lokesh Bheemayya, Arihant Jayawant Kadapure

et al.

Published: April 1, 2025

Citations

0
One-Pot Synthesis of N-Fused Quinolone-4 Tetracyclic Scaffolds from 2,2-Disubstituted Indolin-3-ones DOI Creative Commons
Nikolai A. Arutiunov, Anna M. Zatsepilina, Anna A. Aksenova

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: 9(45), P. 45501 - 45517

Published: Oct. 29, 2024

A cascade transformation of C2-quaternary indoxyls leading to an efficient assembly complex (dihydro)indolo[1,2-a]quinolin-5-one ring systems is reported. The method involves the gram-scale preparation 2-(2-aryl-3-oxoindolin-2-yl)-2-phenylacetonitriles which are then converted with methyl ketones corresponding 2-(2-oxo-2-aryl(alkyl)ethyl)-2-phenylindolin-3-ones. latter can either be isolated good yields (75–96%) or, in case o-nitroacetophenone, used situ for further base-assisted intramolecular SNAr cyclization resulting indoxyl-fused quinolone-4 hybrids (up 95%).

Language: Английский

Citations

2
Photo- and Electro-chemical Strategies for Indazole Synthesis DOI Creative Commons
Binbin Huang

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: unknown, P. 100116 - 100116

Published: Dec. 1, 2024

The indazole core is prevalently found in the structures of bioactive molecules, demonstrating promising potential medicinal chemistry and drug discovery, which therefore has attracted sustained attention from synthetic community. Over recent decades, significant progress been achieved both organic photocatalysis electrosynthesis, offering novel approaches for efficient sustainable synthesis various functionalized indazoles. This mini-review highlights emerging methodological advancements photo-/electro-chemical two common forms indazole, namely 1H- 2H-indazoles, are classified by specific intramolecular bond formation patterns: (1) C-C formation, (2) C-N (3) N-N formation. reaction conditions, representative scopes, mechanistic understandings these protocols emphasized, to elucidate advantages limitations current strategies, with an aim inspire future innovations that may address challenges modern synthesis.Graphical abstractTo create your abstract, type over instructions template box below. Fonts or abstract dimensions should not be changed altered.

Language: Английский

Citations

2
Synthetic approaches for quinoline heterocycles fused at face b: A review DOI
Nada M. Mohamed, Najla A. Alshaye, Mai Mostafa

et al.

Synthetic Communications, Journal Year: 2024, Volume and Issue: 54(19), P. 1629 - 1651

Published: Aug. 19, 2024

Quinolines are very important materials in organic synthesis due to their wide range of biological activities as well representing one the most research area medicinal chemistry. have many applications design and multiple heterocyclic compounds with a variety significance. fused heterocycles at face b using different synthetic methodologies variable precursors reaction conditions were aim current review.

Language: Английский

Citations

1
Selective Preparation of Pyrrolo[2,3‐c]tetrahydroquinolines and Indolo[3,2‐c]tetrahydroquinolines through N‐Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl‐Tethered Oximes with Diaryliodonium Salts DOI Open Access

Chang‐Rui Nie,

Mingyao Pan,

Rong Deng

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 25, 2024

Abstract We describe a selective preparation of variety functionalized pyrrolo[2,3‐ c ]tetrahydroquinolines and indolo[3,2‐ in 40–82% 40–80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N ‐arylation, intramolecular [3+2] cycloaddition, [1.3] or [3,3]‐rearrangement N−O bond total three steps. Experimental studies revealed that EtOAc solvent copper(II)‐catalyst played crucial roles on the formation these two tetrahydroquinoline scaffolds. Moreover, scaffolds could be converted into various building blocks by further transformations.

Language: Английский

Citations

1