Flavin mimetics: Synthesis and photophysical properties

Dora M. Răsădean; Takashi Machida; Kazuki Sada; Christopher R. Pudney; G. Dan Pantoș

doi:10.1016/j.tet.2021.131925

Flavin mimetics: Synthesis and photophysical properties

Dora M. Răsădean, Takashi Machida, Kazuki Sada, Christopher R. Pudney, G. Dan Pantoș

Research output: Contribution to journal › Article › peer-review

Abstract

We report the synthesis of new isoalloxazines using a microwave-assisted approach to make N-substituted-2-nitroanilines followed by one-pot reduction and condensation via Hemmerich's method. The influence of substituents on positions 7, 8, and 10 of flavin core on the optical properties is investigated. The aliphatic functionalities on N10 give rise to quantum yields of 0.7, while aromatic side-chains quench fluorescence. Relaxed geometries (DFT) of chiral and achiral derivatives have been used for TD-DFT calculations, which yielded good agreement with the experimental UV and CD data.

Original language	English
Article number	131925
Journal	Tetrahedron
Early online date	13 Jan 2021
DOIs	https://doi.org/10.1016/j.tet.2021.131925
Publication status	E-pub ahead of print - 13 Jan 2021

Keywords

Chirality
Flavin
Fluorescence
Isoalloxazine
Microwave synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2021.131925

Link to publication in Scopus

Cite this

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title = "Flavin mimetics: Synthesis and photophysical properties",

abstract = "We report the synthesis of new isoalloxazines using a microwave-assisted approach to make N-substituted-2-nitroanilines followed by one-pot reduction and condensation via Hemmerich's method. The influence of substituents on positions 7, 8, and 10 of flavin core on the optical properties is investigated. The aliphatic functionalities on N10 give rise to quantum yields of 0.7, while aromatic side-chains quench fluorescence. Relaxed geometries (DFT) of chiral and achiral derivatives have been used for TD-DFT calculations, which yielded good agreement with the experimental UV and CD data.",

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AU - Sada, Kazuki

AU - Pudney, Christopher R.

AU - Pantoș, G. Dan

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AB - We report the synthesis of new isoalloxazines using a microwave-assisted approach to make N-substituted-2-nitroanilines followed by one-pot reduction and condensation via Hemmerich's method. The influence of substituents on positions 7, 8, and 10 of flavin core on the optical properties is investigated. The aliphatic functionalities on N10 give rise to quantum yields of 0.7, while aromatic side-chains quench fluorescence. Relaxed geometries (DFT) of chiral and achiral derivatives have been used for TD-DFT calculations, which yielded good agreement with the experimental UV and CD data.

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