Photochemistry of 1,<i>n</i>-Dibenzyloxy-9,10-anthraquinones

Sarma, Saurav J.; Jones, Paul B.

doi:10.1021/jo100650u

Cited by 21 publications

(10 citation statements)

References 52 publications

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“…35 Various alkylations (Schemes 2–4) at the hydroxyl group were accomplished using standard conditions, namely benzyl ( 6 ), isopropyl ( 9 ), and methyl ( 11 ) protection in order to probe the S4 pocket. 36, 37 …”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, biochemical studies, cellular characterization, and structure-based computational studies of small molecules targeting the urokinase receptor

Wang

Knabe

et al. 2012

Bioorganic & Medicinal Chemistry

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The urokinase receptor (uPAR) serves as a docking site to the serine protease urokinase-type plasminogen activator (uPA) to promote extracellular matrix (ECM) degradation and tumor invasion and metastasis. Previously, we had reported a small molecule inhibitor of the uPAR•uPA interaction that emerged from structure-based virtual screening. Here, we measure the affinity of a large number of derivatives from commercial sources. Synthesis of additional compounds was carried out to probe the role of various groups on the parent compound. Extensive structure-based computational studies suggested a binding mode for these compounds that led to a structure-activity relationship study. Cellular studies in non-small cell lung cancer (NSCLC) cell lines that include A549, H460 and H1299 showed that compounds blocked invasion, migration and adhesion. The effects on invasion of active compounds were consistent with their inhibition of uPA and MMP proteolytic activity. These compounds showed weak cytotoxicity consistent with the confined role of uPAR to metastasis.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, biochemical studies, cellular characterization, and structure-based computational studies of small molecules targeting the urokinase receptor

Wang

Knabe

et al. 2012

Bioorganic & Medicinal Chemistry

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“…BP and its derivatives are also important chromophores that, after absorption of a photon of light, may give rise to a wide range of reactions in biological systems such as electron transfer, hydrogen abstraction, triplet–triplet energy transfer, and photosensitization reactions that in some cases can cause damage to DNA and/or other biological molecules . The photochemistry of anthraquinone (AQ) derivatives in aqueous solutions has also received increasing interest as a platform for developing photoremovable protecting groups …”

Section: Introductionmentioning

confidence: 99%

Ketyl Radical Formation via Proton-Coupled Electron Transfer in an Aqueous Solution versus Hydrogen Atom Transfer in Isopropanol after Photoexcitation of Aromatic Carbonyl Compounds

Zhang

et al. 2016

J. Org. Chem.

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The excited nπ* and ππ* triplets of two benzophenone (BP) and two anthraquinone (AQ) derivatives have been observed in acetonitrile, isopropanol, and mixed aqueous solutions using time-resolved resonance Raman spectroscopic and nanosecond transient absorption experiments. These experimental results, combined with results from density functional theory calculations, reveal the effects of solvent and substituents on the properties, relative energies, and chemical reactivities of the nπ* and ππ* triplets. The triplet nπ* configuration was found to act as the reactive species for a subsequent hydrogen atom transfer reaction to produce a ketyl radical intermediate in the isopropanol solvent, while the triplet ππ* undergoes a proton-coupled electron transfer (PCET) in aqueous solutions to produce a ketyl radical intermediate. This PCET reaction, which occurs via a concerted proton transfer (to the excited carbonyl group) and electron transfer (to the excited phenyl ring), can account for the experimental observation by several different research groups over the past 40 years of the formation of ketyl radicals after photolysis of a number of BP and AQ derivatives in aqueous solutions, although water is considered to be a relatively "inert" hydrogen-donor solvent.

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“…Photochemistry of 1-benzyloxy-9,10-anthraquinones 108 was described by Sharma and Jones (2010). This compound also undergoes intramolecular d H-abstraction which further leads to the oxidative cleavage of the 1-alkoxy group as an aldehyde (Blankespoor et al, 1991(Blankespoor et al, , 1995(Blankespoor et al, , 2002Smart et al, 1997).…”

Section: Synthesis Of 1-hydroxy-910-anthraquinonesmentioning

confidence: 99%

Photochemical studies: Chromones, bischromones and anthraquinone derivatives

Yusuf

Solanki

Jain

et al. 2019

Arabian Journal of Chemistry

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Photochemical reaction is a chemical reaction initiated by the absorption of energy in the form of light resulting in different types of reaction. Chromones, bischromones and anthraquinones are the bichromophoric molecules which contain the carbonyl group and double bond in conjugation. Photochemical reactions of these compounds result in the formation of such molecules which are not obtained via conventional methods. This review article describes the photochemical transformations of chromones, bischromones and anthraquinone derivatives and here main emphasis has been laid upon the intramolecular photochemical H-abstraction reactions that provide many exotic heterocyclics as the final photoproducts. ª 2014 Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/3.0/).

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Photochemistry of 1,n-Dibenzyloxy-9,10-anthraquinones

Cited by 21 publications

References 52 publications

Design, synthesis, biochemical studies, cellular characterization, and structure-based computational studies of small molecules targeting the urokinase receptor

Design, synthesis, biochemical studies, cellular characterization, and structure-based computational studies of small molecules targeting the urokinase receptor

Ketyl Radical Formation via Proton-Coupled Electron Transfer in an Aqueous Solution versus Hydrogen Atom Transfer in Isopropanol after Photoexcitation of Aromatic Carbonyl Compounds

Photochemical studies: Chromones, bischromones and anthraquinone derivatives

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