Streamlined Access to Novel Activators and Degraders of the Aryl Hydrocarbon Receptor through a Rewired Multicomponent Reaction DOI Creative Commons
Ouldouz Ghashghaei,

Frederick Hartung,

Marina Pedrola

и другие.

Опубликована: Окт. 19, 2022

A rewired Yonemitsu multicomponent reaction was designed to readily synthesize a family of 6-substituted indolocarbazoles. In this approach, indole 2-carboxaldehyde and nucleophilic species directly yield the final adducts through domino reaction. The scope new process analyzed, range aldehydes nucleophiles established. Comparative studies with analogous compounds reveal important details on mechanism. Experimental computational address conformational behavior representative adducts, determining their potential chirality. These novel structures are potent activating ligands human aryl hydrocarbon receptor, importantly being non-toxic. Furthermore, scaffold may be included in 2-step synthesis (homo)-PROTACs that efficiently specifically degrade receptor. Our approach allows control target biomedicine chemistry.

Язык: Английский

Highlighting multicomponent reactions as an efficient and facile alternative route in the chemical synthesis of organic-based molecules: a tremendous growth in the past 5 years DOI Creative Commons
Reagan L. Mohlala, Thompho Jason Rashamuse,

E. Mabel Coyanis

и другие.

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Сен. 18, 2024

Since Strecker’s discovery of multicomponent reactions (MCRs) in 1850, the strategy applying an MCR approach has been use for over a century. Due to their ability quickly develop molecular diversity and structural complexity interest, MCRs are considered efficient organic synthesis. Although such as Ugi, Passerini, Biginelli, Hantzsch widely studied, this review emphasizes significance selective elegantly produce compounds potential medicinal chemistry industrial material science applications, well sustainable methods. During synthesis, provide advantages atom economy, recyclable catalysts, moderate conditions, preventing waste, avoiding solvent use. also reduce number sequential multiple one step.

Язык: Английский

Процитировано

7

Polymer-Immobilized Dioxidotungsten(VI) Complex as a Highly Sustainable Catalyst in the One-Pot, Four-Component Synthesis of Bioactive Pyranopyrazole Molecules DOI
Mannar R. Maurya, Naveen Kumar,

Monojit Nandi

и другие.

Topics in Catalysis, Год журнала: 2025, Номер unknown

Опубликована: Янв. 27, 2025

Язык: Английский

Процитировано

0

A Multicomponent Reaction-Based Platform Opens New Avenues in Aryl Hydrocarbon Receptor Modulation DOI Creative Commons
Pau Nadal Rodríguez,

Frederick Hartung,

Marina Pedrola

и другие.

ACS Central Science, Год журнала: 2025, Номер unknown

Опубликована: Апрель 10, 2025

A multidisciplinary platform is presented to address aryl hydrocarbon receptor (AhR) modulation. rewired Yonemitsu multicomponent reaction with indole 2-carboxaldehydes and nucleophilic species was designed access a family of 6-substituted indolocarbazoles. The conformational behavior these compounds examined rationalize their axial chirality. In silico docking molecular simulations highlighted key features implicated in binding AhR. Furthermore, the synthesis linkable derivatives allowed direct development conjugated entities. Reporter gene target expression analyses identified novel structures as potent noncytotoxic activating AhR ligands, that can be extended bifunctional molecules. anti-inflammatory properties agonists were assessed interleukin-13 treated keratinocytes. Altogether, synergistic research synthetic computational chemistry integrated biological studies opens avenues toward understanding roles targeted therapeutics.

Язык: Английский

Процитировано

0

LiAl-LDH: a heterogeneous catalyst for the multicomponent synthesis of coumarin-3-carboxamide derivatives DOI Creative Commons

Rosalía Torralba,

Franchescoli D. Velázquez-Herrera, Manuel Velasco

и другие.

Research on Chemical Intermediates, Год журнала: 2025, Номер unknown

Опубликована: Май 2, 2025

Язык: Английский

Процитировано

0

Multicomponent Cross-Dehydrogenative Coupling of Imidazo[1,2-a]pyridine: Access to Abnormal Mannich and Mannich-Type Reaction DOI
S. M. Wahidur Rahaman,

Suhag Singh Sahay,

Annu Kumari

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(15), С. 10773 - 10784

Опубликована: Июль 17, 2024

This study showcases successfully switchable approaches to accomplish the C3-aryl methylation and C3- amino of privileged nitrogen-containing pharmaceutical compounds "imidazopyridines" with distinct amines, which surmounts long-standing requirement for a superfluous directing group. These two transformations manifest pronounced regio- chemo-divergent behavior, demonstrating unprecedented multicomponent "abnormal Mannich Mannich-type" reactions. The remarkable environmentally benign protocol has been efficiently extended concise synthesis late-stage derivatization.

Язык: Английский

Процитировано

3

Recent trends for chemoselectivity modulation in one-pot organic transformations DOI Creative Commons

Hiren R. Chaudhary,

Divyang M. Patel

RSC Advances, Год журнала: 2024, Номер 14(42), С. 31072 - 31116

Опубликована: Янв. 1, 2024

This article describes recent advances in one-pot chemoselective reactions and their mechanism insights. Here, the substrate, catalyst, solvent, temperature play a vital role modulating chemoselectivity.

Язык: Английский

Процитировано

3

A new type of heterogeneous catalysis strategy for organic reactions: Ugi-3CR catalyzed by highly stable MOFs with exposed carboxyl groups DOI

Jinni Liu,

Yong-Shuang Li, Na Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(22), С. 6179 - 6186

Опубликована: Янв. 1, 2022

A mild and highly efficient Ugi-3CR using a novel Cu-COOH@MOF-6 as the catalyst has been developed, which provides facile access to α-amino amides. The recycling test XRD images showed that catalytic system good stability recyclability.

Язык: Английский

Процитировано

9

Iron‐Mediated C−H Functionalization of Unactivated Alkynes for the Synthesis of Derivatized Dihydropyrrolones: Regioselectivity Under Thermodynamic Control DOI

Austin C. Durham,

Cindy R. Liu,

Yiming Wang

и другие.

Chemistry - A European Journal, Год журнала: 2023, Номер 29(45)

Опубликована: Май 19, 2023

Cyclopentadienyliron dicarbonyl-based complexes present opportunities for underexplored disconnections in synthesis. Access to challenging dihydropyrrolone products is achieved by propargylic C-H functionalization of alkynes the formation cyclic organoiron species. Excellent regioselectivity unsymmetrical observed many cases. Notably, under these stoichiometric conditions diverges from those previously catalysis, occurring at more-substituted terminus alkyne, allowing methine and quaternary centers. Divergent demetallation intermediate gives access chemically diverse which are amenable further functionalization.

Язык: Английский

Процитировано

5

Multicomponent reactions as a privileged tool for multitarget-directed ligand strategies in Alzheimer’s disease therapy DOI
Sylvain Grosjean, Irène Pachón-Angona, Michella Dawra

и другие.

Future Medicinal Chemistry, Год журнала: 2022, Номер 14(21), С. 1583 - 1606

Опубликована: Окт. 20, 2022

Among neurodegenerative pathologies affecting the older population, Alzheimer's disease is most common type of dementia and leads to neurocognitive behavioral disorders. It a complex progressive age-related multifactorial characterized by series highly interconnected pathophysiological processes. Within last decade, multitarget-directed ligand strategy has emerged as viable approach developing molecules that exhibit several pharmacophores which can target different enzymes receptors involved in pathogenesis disease. Herein, we focus on using multicomponent reactions such Hantzsch, Biginelli Ugi develop these biologically active multitopic ligands.

Язык: Английский

Процитировано

4

Organocatalyst 1,4-diazabicyclo [2.2.2]octane (DABCO)-catalyzed Sustainable Synthesis of Bis-thiazolidinones Derivatives and their Spectral and DFT Analysis DOI
Saloni Sahal, Mamta Chahar, Har Lal Singh

и другие.

Current Organic Chemistry, Год журнала: 2024, Номер 28(9), С. 725 - 732

Опубликована: Апрель 17, 2024

Abstract: Organocatalyst 1,4-diazabicyclo [2.2.2]octane (DABCO) has proven to be an efficient and environmentally friendly catalyst in the multicomponent reaction involving aldehydes, ethylenediamine, thioglycolic acid under microwave conditions. DABCO stands out among other organic catalysts due its cost-effectiveness, non-toxic nature, conscious profile. The method employed this study exhibited exceptional attributes, such as high yields, swift times, atom economy, reusability, minimal loading. Additionally, there were excellent yields of products (90-94%). melting points, UV-Vis, IR, 1HNMR, 13CNMR, used analyze produced compounds. invitro antibacterial activity synthesized compounds was investigated against pathogenic strains E. coli Bacillus supstalis, results obtained further explained with help DFT molecular orbital calculations. Moreover, compound 4b found most potent agent amongst all tested

Язык: Английский

Процитировано

0