Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel–Crafts Alkylation Reaction DOI
Patamawadee Silalai, Rungnapha Saeeng

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4052 - 4065

Опубликована: Март 7, 2023

This paper reports the acid-controlled divergent synthesis of 3-pyrrolidin-2-yl-1H-indoles and symmetric unsymmetrical bis(indolyl)methanes (BIMs) through photocatalyzed decarboxylative coupling Friedel-Crafts alkylation reactions, respectively. The protocol involves C-H functionalization, switching formation two products, room-temperature conditions, low photocatalyst loadings, without strong oxidant, moderate to excellent yields. method has been applied for natural product vibrindole A 1,1-bis(1H-indol-3-yl)-2-phenylethane.

Язык: Английский

Tryptophan-specific modification and diversification of peptides and proteins DOI
S K Kundu, A. Bandyopadhyay, Rajib Sarkar

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

This review provides an account of the tryptophan-specific conjugation peptides and proteins its extensive application in imaging living cells, radiolabelling proteins, protein engineering, etc .

Язык: Английский

Процитировано

2

Unlocking Diversity: From Simple to Cutting-Edge Synthetic Methodologies of Bis(indolyl)methanes DOI
Pankaj Teli, Shivani Soni, Sunita Teli

и другие.

Topics in Current Chemistry, Год журнала: 2024, Номер 382(1)

Опубликована: Фев. 25, 2024

Язык: Английский

Процитировано

11

Metal-Free Late-Stage Alkylation of Tryptophan and Tryptophan-Containing Peptides with 1,3-Dithiane Derivatives DOI

Mingming Mao,

Jia Li,

Kang Dong

и другие.

Organic Letters, Год журнала: 2023, Номер 25(31), С. 5784 - 5789

Опубликована: Июль 28, 2023

Late-stage diversification of structurally complex peptides has enormous potential for drug discovery and molecular imaging. We report a simple, metal-free, late-stage reductive C2 alkylation tryptophan tryptophan-containing using readily available 1,3-dithianes. This protocol wide substrate scope an excellent tolerance reactive functional groups.

Язык: Английский

Процитировано

11

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

Divergent Synthesis of 3-Pyrrolidin-2-yl-1H-indoles, Symmetric and Unsymmetric Bis(Indolyl)Methanes (BIMs) through Photocatalyzed Decarboxylative Coupling/Friedel–Crafts Alkylation Reaction DOI
Patamawadee Silalai, Rungnapha Saeeng

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(7), С. 4052 - 4065

Опубликована: Март 7, 2023

This paper reports the acid-controlled divergent synthesis of 3-pyrrolidin-2-yl-1H-indoles and symmetric unsymmetrical bis(indolyl)methanes (BIMs) through photocatalyzed decarboxylative coupling Friedel-Crafts alkylation reactions, respectively. The protocol involves C-H functionalization, switching formation two products, room-temperature conditions, low photocatalyst loadings, without strong oxidant, moderate to excellent yields. method has been applied for natural product vibrindole A 1,1-bis(1H-indol-3-yl)-2-phenylethane.

Язык: Английский

Процитировано

5