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Keywords = β-Fluoro-β-nitrostyrene

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23 pages, 8658 KiB  
Article
Efficient Synthesis of Core-Fluorinated BODIPY-3,5-Diamides
by Victoria E. Shambalova, Sofiya R. Mikheeva, Alexander S. Aldoshin, Anna A. Moiseeva, Evgeniya A. Safonova, Yulia G. Gorbunova and Valentine G. Nenajdenko
Int. J. Mol. Sci. 2025, 26(10), 4484; https://doi.org/10.3390/ijms26104484 - 8 May 2025
Viewed by 592
Abstract
A modular synthesis of a new family of core-fluorinated BODIPYs was elaborated. β-Fluoro-β-nitrostyrenes were used as starting materials to prepare a set of mono-fluorinated pyrrole-2-amides using the Barton-Zard reaction with 2-isocyanoacetamides. The prepared monofluorinated building blocks were successively transformed into [...] Read more.
A modular synthesis of a new family of core-fluorinated BODIPYs was elaborated. β-Fluoro-β-nitrostyrenes were used as starting materials to prepare a set of mono-fluorinated pyrrole-2-amides using the Barton-Zard reaction with 2-isocyanoacetamides. The prepared monofluorinated building blocks were successively transformed into the corresponding dipyrromethanes and 1,7-difluoro-BODIPY-3,5-diamides. As a result, a new family of luminophores with a combination of fluorescence and photosensitizing properties was obtained. The photophysical properties of novel BODIPYs were studied by UV-vis and fluorescence spectroscopy, cyclic voltammetry and DFT calculations. In addition, their ability to generate singlet oxygen was assessed. The properties of 1,7-difluoro-BODIPY-3,5-diamides were compared with their analogues to reveal the substituent effect at the 3,5-positions. The fluorescent properties of the obtained dyes were significantly improved in comparison to their 3,5-diester analogous. Full article
(This article belongs to the Special Issue Heterocyclic Compounds: Synthesis, Design, and Biological Activity)
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28 pages, 5620 KiB  
Article
An Easy Synthesis of Monofluorinated Derivatives of Pyrroles from β-Fluoro-β-Nitrostyrenes
by Alexander S. Aldoshin, Andrey A. Tabolin, Sema L. Ioffe and Valentine G. Nenajdenko
Molecules 2021, 26(12), 3515; https://doi.org/10.3390/molecules26123515 - 9 Jun 2021
Cited by 5 | Viewed by 2699
Abstract
The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1H-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a [...] Read more.
The catalyst-free conjugate addition of pyrroles to β-Fluoro-β-nitrostyrenes was investigated. The reaction was found to proceed under solvent-free conditions to form 2-(2-Fluoro-2-nitro-1-arylethyl)-1H-pyrroles. The effectiveness of this approach was demonstrated through the preparation of a series of the target products in a quantitative yield. The kinetics of a conjugate addition of pyrrole was studied in detail to reveal the substituent effect and activation parameters of the reaction. The subsequent base-induced elimination of nitrous acid afforded a series of novel 2-(2-Fluoro-1-arylvinyl)-1H-pyrroles prepared in up to an 85% isolated yield. The two-step sequence herein proposed is an indispensable alternative to a direct reaction with elusive and unstable 1-Fluoroacetylenes. Full article
(This article belongs to the Special Issue Organofluorine Chemistry and Beyond)
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15 pages, 391 KiB  
Article
A Study of Fluorinated β-Nitrostyrenes as Antimicrobial Agents
by King Lo, Hugh Cornell, Gina Nicoletti, Neale Jackson and Helmut Hügel
Appl. Sci. 2012, 2(1), 114-128; https://doi.org/10.3390/app2010114 - 23 Feb 2012
Cited by 18 | Viewed by 7542
Abstract
The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was [...] Read more.
The effect of variously fluorine-substituted β-methyl-β-nitrostyrenes on their antimicrobial activity was investigated. Their efficacy was determined by minimum inhibition concentration (MIC) in cultures of Gram positive and Gram negative bacteria and a fungus. Highest activity against the Gram negative bacterium, E.coli, was achieved with 4-fluorine-aryl substituted β-methyl-β-nitrostyrenes, while most compounds gave excellent results against gram positive bacteria. Importantly, the addition of the β-methyl group profoundly enhanced the antibacterial activity of the compounds tested. The comparative KD values for the most potent compounds against E.coli were much lower than those required for the gram positive and fungus counterparts. This investigation illustrated that fluorine substituted nitropropenylarenes have enhanced antimicrobial activity suitable for antibiotic applications. Full article
(This article belongs to the Special Issue Organo-Fluorine Chemical Science)
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