On the Formation and Reactivity of 2-Alkylidene-benzopyrans and their 2-amino-5,6-benzo-2H-pyran precursors

Kanitz, Andreas; Hartmann, Horst; Czerney, Peter

doi:10.1002/prac.19983400106

Cited by 10 publications

(3 citation statements)

References 15 publications

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“…Inspired by these discoveries, we turned our attention to 3 , a low‐polarity fluorophore (Figure a) . Compound 3 has longer absorption wavelengths than many conventional fluorophores (such as coumarin, naphthalimide, acedan, BODIPY and rhodamine derivatives).…”

Section: Resultsmentioning

confidence: 99%

“…[15] Inspired by these discoveries, we turned our attention to 3, al ow-polarity fluorophore (Figure 1a). [16] Compound 3 has longer absorption wavelengthsthan many conventional fluorophores (such as coumarin, naphthalimide, acedan, BODIPY and rhodamine derivatives).S ynthesis of 3 is facile, and the availability of an amino group in this compound makes further chemicals ubstitution and functionalization straightforward. More importantly,o ur quantum chemical calculations show that the TP absorption cross-section( s)o f3 is about 4-20 times larger than those of popular naphthalimide, acedan, rhodamine, and Nile Red dyes (see the Supporting Information 2).…”

Section: Molecular Design Strategiesmentioning

confidence: 99%

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Rational Development of Near‐Infrared Fluorophores with Large Stokes Shifts, Bright One‐Photon, and Two‐Photon Emissions for Bioimaging and Biosensing Applications

Zhou

Wang

Tan

et al. 2017

Chemistry A European J

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Fluorophores with near-infrared emissions play a crucial role in numerous bioimaging and biosensing applications, owing to their deep penetration depths, low auto-fluorescence, and minimal tissue damages. Herein, the rational development of a new class of near-infrared fluorophores with bright one-photon and two-photon emissions at ≈740 nm, large Stokes shifts (≈80 nm), significant two-photon action absorption cross-section (≈185 GM at 820 nm), excellent water solubility, outstanding photostability, and low toxicity is reported. Their biological applications in mitochondrial labelling, deep tissue imaging, and H S detection in live cells and mice are also demonstrated. In addition, a rational design strategy for enlarging the Stokes shifts and enhancing two-photon emissions of these fluorophores is presented. These fluorophores will serve as a useful platform for developing novel imaging and sensing agents, and the design methodologies will inspire the molecular engineering of abundant high-performance near-infrared fluorophores.

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Section: Resultsmentioning

confidence: 99%

Section: Molecular Design Strategiesmentioning

confidence: 99%

Rational Development of Near‐Infrared Fluorophores with Large Stokes Shifts, Bright One‐Photon, and Two‐Photon Emissions for Bioimaging and Biosensing Applications

Zhou

Wang

Tan

et al. 2017

Chemistry A European J

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“…Two out of the five synthesized compounds are novel. The compounds PS-CP-SAL [6,11], PS-CP-4MO [11], and PS-CP-5Br [9] have already been reported previously though their biological activities have not been evaluated till date. The UV-vis spectra show three distinctive peaks, foremost in between 250 and 260 nm, followed by the subsequent peak in the range of 290 and 320 nm and the final peak between 400 and 530 nm.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Benzopyrylium salts as new anticancer, antibacterial, and antioxidant agents

et al. 2021

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Benzopyrylium salts are an unexplored class of compounds and as a first, this study reports them as potential therapeutic agents. In this effort we pursue the synthesis and in vitro anticancer, antibacterial and antioxidant properties of some novel benzopyrylium salts. The benzopyrylium salts were synthesized and further characterized via UV-vis, IR, 1 H-NMR, 13 C-NMR and mass spectrometry. The benzopyrylium salts were tested in vitro for anticancer activity across NCI 60 cell line panel. PS-CP-4MO showed the best activity against the MDA-MB-435 cell line of melanoma cancer in terms of the least GI 50 (1.78 μM), TGI (3.47 μM) and LC 50 (6.77 μM) values and showed selectivity against melanoma, colon cancer and leukemia. Mechanistic studies indicate that this compound inhibits MCF-7 cancer cells by inducing apoptosis and abrogates colony formation and wound healing in the cancer cells. Antibacterial studies show that some of the benzopyrylium salts are active on S. aureus (ATCC 29213) and the best active compound PS-CP-5Cl has a MIC of 8 μg/mL. Antioxidant studies indicate that they have good free radical scavenging properties (PS-CP-5Cl showed activity 1.48 times ascorbic acid). Fulfillment of the Lipinski's parameters of the benzopyrylium salts in silico showed tremendous drug likeness as potential pharmacophore leads.

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The Vilsmeier Reaction of Non‐Aromatic Compounds

Jones

Stanforth

2000

Organic Reactions

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This chapter extends the discussion to reactions between the Vilsmeier‐Haack reagent (subsequently referred to as the Vilsmeier reagent for brevity) and any other compounds in which a carbon‐carbon bond is formed. The discussion thus excludes reactions in which the Vilsmeier reagent acts as a chlorinating agent (for example in the preparation of acid chlorides), or in which it forms carbon‐oxygen or carbon‐nitrogen bonds, unless these are accompanied by formation of a carbon‐carbon bond. For a discussion of the nature of the reagent and of the mechanism of the reaction, the earlier chapter in vol. 49 should be consulted. There are also a number of reviews that deal at length with mechanisms of reactions involving the Vilsmeier reagent, notably those by Jutz and Marson, and hence this chapter will concentrate on applications, with brief mention of mechanisms when necessary. Wizinger has pointed out that alkenes could react with the Vilsmeier reagent, but his only examples were styrenes where the intermediate carbocation has considerable stability. Hydrolysis gives the cinnamaldehyde. In principle, any alkene which is not too sterically hindered can undergo this reaction, but the Vilsmeier reagent has low reactivity as an electrophile, and in practice activation is often necessary. The addition depends on the HOMO of the alkene, and anything increasing the HOMO energy will aid reaction, as for example further conjugation (dienes, trienes, etc.) or the presence of an electron‐donating substituent. Hence aldehydes and ketones are active in their enol forms, and enol ethers and enamines are good substrates. Indeed, all additions covered by this chapter can be regarded as alkene additions, even those on active methyl groups attached to electron‐deficient rings. As with any reaction involving carbocation intermediates, rearrangements are possible; the initial products are sometimes enamines, and this can give rise to polysubstitution. The substrates are grouped into eleven major subsections; references to reviews of particular relevance will be found in the appropriate subsection.

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On the Formation and Reactivity of 2-Alkylidene-benzopyrans and their 2-amino-5,6-benzo-2H-pyran precursors

Cited by 10 publications

References 15 publications

Rational Development of Near‐Infrared Fluorophores with Large Stokes Shifts, Bright One‐Photon, and Two‐Photon Emissions for Bioimaging and Biosensing Applications

Rational Development of Near‐Infrared Fluorophores with Large Stokes Shifts, Bright One‐Photon, and Two‐Photon Emissions for Bioimaging and Biosensing Applications

Benzopyrylium salts as new anticancer, antibacterial, and antioxidant agents

The Vilsmeier Reaction of Non‐Aromatic Compounds

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