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

3 Citations (SciVal)

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
Volume	82
Early online date	13 Jan 2021
DOIs	https://doi.org/10.1016/j.tet.2021.131925
Publication status	Published - 26 Feb 2021

Bibliographical note

Funding Information:
This paper is a contribution to special issue in memory of Prof. Jon Williams. An excellent colleague and chemist, he was a strong presence in our department who is sorely missed. The authors gratefully acknowledge an EPSRC DTP (to D.M.R.) and the University of Bath for a visiting PhD researcher position (T.M.) which was also supported by Japan Student Services Organization (JASSO).

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

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.",

keywords = "Chirality, Flavin, Fluorescence, Isoalloxazine, Microwave synthesis",

author = "R{\u a}s{\u a}dean, {Dora M.} and Takashi Machida and Kazuki Sada and Pudney, {Christopher R.} and Pantoș, {G. Dan}",

note = "Funding Information: This paper is a contribution to special issue in memory of Prof. Jon Williams. An excellent colleague and chemist, he was a strong presence in our department who is sorely missed. The authors gratefully acknowledge an EPSRC DTP (to D.M.R.) and the University of Bath for a visiting PhD researcher position (T.M.) which was also supported by Japan Student Services Organization (JASSO). ",

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language = "English",

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T2 - Synthesis and photophysical properties

AU - Răsădean, Dora M.

AU - Machida, Takashi

AU - Sada, Kazuki

AU - Pudney, Christopher R.

AU - Pantoș, G. Dan

N1 - Funding Information: This paper is a contribution to special issue in memory of Prof. Jon Williams. An excellent colleague and chemist, he was a strong presence in our department who is sorely missed. The authors gratefully acknowledge an EPSRC DTP (to D.M.R.) and the University of Bath for a visiting PhD researcher position (T.M.) which was also supported by Japan Student Services Organization (JASSO).

PY - 2021/2/26

Y1 - 2021/2/26

N2 - 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.

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.

KW - Chirality

KW - Flavin

KW - Fluorescence

KW - Isoalloxazine

KW - Microwave synthesis

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U2 - 10.1016/j.tet.2021.131925

DO - 10.1016/j.tet.2021.131925

M3 - Article

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SN - 0040-4020

VL - 82

JO - Tetrahedron

JF - Tetrahedron

M1 - 131925

ER -

Flavin mimetics: Synthesis and photophysical properties

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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Fingerprint

Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Walk-up Liquid Chromatography Electrospray quadrupole Time-of-Flight Mass Spectrometer (LC-ESI-QTOF MS)

Cite this

Flavin mimetics: Synthesis and photophysical properties

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Equipment

Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Walk-up Liquid Chromatography Electrospray quadrupole Time-of-Flight Mass Spectrometer (LC-ESI-QTOF MS)

Cite this