Fluorofuroxans: Synthesis and Application as Photoinduced Nitric Oxide Donors

Andõ, Akira; Matsubara, Ryosuke; Takazawa, Saori; Shimada, Toshiyuki; Hayashi, Masahiko

doi:10.1002/ajoc.201600149

Cited by 19 publications

(29 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In all cases, no significant byproduct formation is observed. In contrast to the photo-isomerization of 4fluorofuroxans, where the proportion of the post-isomerization isomer (3-fluorofuroxan) reached 90% at the PS, [6] the photoisomerization of 4-alkoxy furoxans affords a lower proportion of the post-isomerization isomer, 3-alkoxy furoxans (<1-85%). Generally, as the alkoxy substituent (OR 2 ) becomes more electron-withdrawing and the aryl-substituent (R 1 ) becomes more electron-donating, 3-alkoxy furoxan 4 becomes more favored than 4-alkoxy furoxan 3.…”

Section: Photo-induced No-releasing Ability Of 4-alkoxy Furoxansmentioning

confidence: 80%

“…[4] Some furoxans have shown thiol-mediated NO-releasing abilities under physiological conditions. [5] We recently [6] established a synthetic route for both fluorofuroxan regioisomers and found that 3-fluoro-substituted isomer 2 generates a greater amount of NO in the presence of a thiol mediator than the 4-fluorosubstituted isomer 1 (Scheme 1). Furthermore, 3-fluorofuroxan 2 is generated from 4-fluorofuroxan 1 by photochemical isomerization.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Study on the Photoinduced Nitric‐Oxide‐Releasing Ability of 4‐Alkoxy Furoxans

et al. 2017

Self Cite

View full text Add to dashboard Cite

Nitric oxide (NO) has a range of biological activities in living systems. Because NO is a gaseous and short-lived molecule, the development of methods to enable a temporally and spatially resolved NO supply has been a challenging task. In this report, 3-aryl 4-alkoxy furoxan is revealed as a potent photo-induced NO-donor. While negligible levels of NO release were observed under ambient fluorescent light, a significant amount of NO was released under UV irradiation ( = 300-400 nm). The thiol mediator bearing a pendant amino group proved indispensable for the NO release from aryl alkoxy furoxans. Analysis of the NO-releasing reaction of aryl alkoxy furoxan revealed that the main coproduct is the corresponding aryl nitrile derived from furoxan ring-fragmentation. From these results, a plausible photo-induced NO-releasing mechanism was proposed, in which the key steps are nucleophilic attack by the thiol at the 3position of furoxan leading to the furoxan ring-fragmentation, and the formation of tetrahydrothiazole bearing a C-nitroso group. Comparison between fluorofuroxan and alkoxy furoxan is also discussed.

show abstract

Section: Photo-induced No-releasing Ability Of 4-alkoxy Furoxansmentioning

confidence: 80%

Section: Introductionmentioning

confidence: 99%

Study on the Photoinduced Nitric‐Oxide‐Releasing Ability of 4‐Alkoxy Furoxans

et al. 2017

Self Cite

View full text Add to dashboard Cite

show abstract

“…Previously we have shown that sensitised NO release of anthraquinone-tethered fluorofuroxans under visible light irradiation generates comparable quantities of NO as the lone fluorofuroxan moiety does under UV irradiation. 21,23 Therefore, we assumed this may be the case for an NDI-furoxan molecule as well. We screened potential furoxans by irradiating them with 300-400 nm light in 50 mM pH 7.4 phosphate buffer and compared the NO release after 2 hours of irradiation (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Recently our research group have made use of the NO donor furoxan and synthesised a series of PINODs. 21,22 4-Fluoroand 4-alkoxy-substituted furoxan derivatives displayed isomerization and photoswitchable release of NO under UV irradiation (Scheme 1a). Constrained with the short UV wavelengths required we consolidated on the furoxan PINOD chemistry by tethering a fluorofuroxan to a visible light absorbing water-soluble anthraquinone molecule 5 (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

A Fluorescent Naphthalenediimide-Alkoxyfuroxan Photoinduced Nitric Oxide Donor

Seymour

Nakata

Tsubaki

et al. 2018

Bulletin of the Chemical Society of Japan

Self Cite

View full text Add to dashboard Cite

We describe the design and facile synthesis of a fluorescent alkoxyfuroxan naphthalenediimide (NDI) hybrid nitric oxide (NO) donor molecule which releases NO under spatiotemporal control when irradiated with visible light (420-600 nm). The hybrid also demonstrates cellular uptake made possible by its fluorescence capability. This research consolidates on our recent work into visible light absorbing photosensitised furoxan NO release by addressing the limitations of previous designs. Key points of photoinduced nitric oxide donors are highlighted such as water solubility, NO release, cellular uptake, fluorescence, and longer absorption wavelengths.

show abstract

“…2 Thus, furoxan has been applied as a building block in hybrid pharmaceutical candidates 3 and switchable NO donors. 4 Most biologically active furoxans reported to date bear one or two carbon substituents on the furoxan ring ( Figure 1). 5 Conventionally, carbon-substituted furoxans were synthesized via the pre-installation of the required carbon substituent on the precursor (e.g.…”

mentioning

confidence: 99%

Synthesis of alkynyl furoxans. Rare carbon–carbon bond-forming reaction on a furoxan ring

et al. 2017

Self Cite

View full text Add to dashboard Cite

A rare carbon-carbon-bond forming reaction on a furoxan ring has been developed. The nucleophilic aromatic substitution (SAr) reaction of 4-nitrofuroxans with alkynyl lithium proceeded with high yields, which enabled the first practical synthesis of both alkynyl furoxan regioisomers. Due to the versatility of the alkyne functional group, various derivatizations of the carbon-carbon triple bond in the afforded products were possible. Thus, this developed method is a convergent approach to a wide spectrum of carbon-substituted furoxans.

show abstract

Fluorofuroxans: Synthesis and Application as Photoinduced Nitric Oxide Donors

Cited by 19 publications

References 47 publications

Study on the Photoinduced Nitric‐Oxide‐Releasing Ability of 4‐Alkoxy Furoxans

Study on the Photoinduced Nitric‐Oxide‐Releasing Ability of 4‐Alkoxy Furoxans

A Fluorescent Naphthalenediimide-Alkoxyfuroxan Photoinduced Nitric Oxide Donor

Synthesis of alkynyl furoxans. Rare carbon–carbon bond-forming reaction on a furoxan ring

Contact Info

Product

Resources

About