A Photochemical Synthesis of 3-Arylcoumarins

Meng, Jiayuan; Shen, M; Fu, De-chao; Gao, Zhen-heng; Wang, Ru‐Ji; Wang, Honggen; Matsuura, Teruo

doi:10.1055/s-1990-26993

Cited by 21 publications

(5 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The natural coumarins gleinene and gleinadiene have been synthesized using 5,7-dimethoxy-8-iodocoumarin as building block [9]. A number of fluorescent 3-arylcoumarins have been synthesised by the photo-coupling of 3-bromocoumarin with aromatic and heteroaromatic compounds [231]. The synthesis of a coumarin, analogue of retinal, that was used for study of the bacteriorhodopsin chromophore binding site, was done via a Wittig olefination of a 3-chloromethylcoumarin (Scheme15) [232].…”

Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

View full text Add to dashboard Cite

Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

show abstract

Section: From Arylcoumarinsmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

890

458

View full text Add to dashboard Cite

show abstract

“…49, 60, 62, 63, and 67), may arise from the well-known photo-homolytic cleavage of these labile carbon-halogen bonds [46]. Not only is there a synthetically useful photo-radical cleavage which uses the 3-brominated/iodinated coumarins as starting materials for a coupling reaction [47] but also such 3bromo/iodo species have demonstrated potent photo-viricidal properties [48]. Park and colleagues advanced a theory in which 3-bromoumbelliferone -with a 7-alkoxy side chain to provide affinity to a viral nucleic acid strand -was photolyzed to a free radical at C 3 which subsequently effected a cleavage of that strand [48].…”

Section: Resultsmentioning

confidence: 99%

Phototoxicity of 7-oxycoumarins with keratinocytes in culture

Guillon

Jan

Heck

et al. 2019

Bioorganic Chemistry

View full text Add to dashboard Cite

Seventy-one 7-oxycoumarins, 66 synthesized and 5 commercially sourced, were tested for their ability to inhibit growth in murine PAM212 keratinocytes. Forty-nine compounds from the library demonstrated light-induced lethality. None was toxic in the absence of UVA light. Structure-activity correlations indicate that the ability of the compounds to inhibit cell growth was dependent not only on their physiochemical characteristics, but also on their ability to absorb UVA light. Relative lipophilicity was an important factor as was electron density in the pyrone ring. Coumarins with electron withdrawing moieties-cyano and fluoro at C 3-were considerably less active while those with bromines or iodine at that location displayed enhanced activity. Coumarins that were found to inhibit keratinocyte growth were also tested for photo-induced DNA plasmid nicking. A concentrationdependent alteration in migration on neutral gels caused by nicking was observed.

show abstract

“…Brominated coumarins have immense synthetic, biological and industrial importance due to their occurance in nature [ 1 ] and applications in pharmaceuticals. They are used for the synthesis of formyl [ 2 ] and aryl derivatives [ 3 ] and serve as important synthetic precursors of furocoumarins and dihydrofurocoumarins, which are widely used as photosensitizers and chemotherapeutic agents to combat skin diseases [ 4 ]. Halocoumarins also exhibit insecticidal and fungicidal properties [ 5 ].…”

Section: Introductionmentioning

confidence: 99%