6457-92-7

Usage

InChI:InChI=1/C12H8O3/c1-7-6-11(13)15-12-8(7)2-3-10-9(12)4-5-14-10/h2-6H,1H3

Upstream product

• 95372-68-2 4-methyl-2-oxo-2H-furo[2,3-h]chromene-8-carboxylic acid ethyl ester 
• 1616-54-2 8-allyl-7-hydroxy-4-methylcoumarin 
• 35722-51-1 4-hydroxy-8-methyl-2,6-dioxo-2H,6H-pyrano<2,3-f>benzopyran 
• 480-97-7 4-hydroxybenzofuran 
• 1361944-39-9 4-benzofuranyl but-2-ynoate 
• 91963-63-2 2-<(4-methyl-2-oxo-2H-7-chromenyl)oxy>ethanol 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 108-46-3 recorcinol 
• 111475-34-4 (8-formyl-4-methyl-2-oxo-2H-chromen-7-yloxy)-acetic acid ethyl ester 
• 14003-96-4 8-formyl-4-methyl-7-hydroxycoumarin 
• 129110-45-8 4-chloro-8-methyl-2,6-dioxo-2H,6H-pyrano<2,3-f>benzopyran 
• 2555-29-5 8-acetyl-7-hydroxy-4-methyl-2H-chromen-2-one 
• 3993-57-5 7-allyloxy-4-methyl-2H-chromen-2-one 
• 100953-18-2 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde 

Relevant academic research and scientific papers

Novel furocoumarin derivatives stimulate melanogenesis in b16 melanoma cells by up-regulation of mitf and tyr family via Akt/GSK3β/β-catenin signaling pathways

The extracts of Ficuscarica L. and Psoralen corylifolia L. are traditional Uygur medicines for the treatment of vitiligo, and its active ingredients furocoumarins, were are found to be the most effective agents against this skin disorder nowadays. Therefore, a series of novel easter derivatives (8a–8p) of furocoumarin were designed and synthesized based on our previous research to improve this activity in the present study. The synthesized derivatives were biologically evaluated for melanin synthesis in murine B16 cells and the SAR (structure-activity relationship) was summarized. Eight derivatives were more potent than positive control (8-MOP, 8-methoxypsoralan), especially compounds 8n (200%) and 8o (197%), which were nearly 1.5-fold potency when compared with 8-MOP (136%). Furthermore, the signaling pathway by which 8n activates the melanin biosynthesis was defined. Our results showed that it not only elevated the melanin content, but also stimulated the activity of tyrosinasein a concentration-dependent manner. Increasing of phosphorylation of Akt (also named PKB, protein kinase B) and non-activated GSK3β (glycogen synthase kinase 3 beta), which inhibited the degradation of β-catenin were observed through Western blot analysis. The accumulation of β-catenin probably led to the activation of transcription of MITF (microphthalmia-associated transcription factor) and TYR (tyrosinase) family, as well as the subsequent induction of melanin synthesis.

Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins

8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/ cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing ole

Palladium-catalyzed intramolecular hydroarylation of 4-benzofuranyl alkynoates. Approach to angelicin derivatives

Intramolecular hydroarylation of 4-benzofuranyl alkynoates using Pd(OAc)2 as catalyst took place selectively and efficiently, giving angular furocoumarin derivatives in high yields. The parent angelicin was obtained in 80% yield by this method.

A convenient synthesis of psoralens

An efficient synthesis (yields >70%) of linear 7H-furo[3,2-g]chromen-7-one derivatives (psoralens or furocoumarins) has been carried out starting from ring-substituted 2-(coumarin-7-yl)oxyaldehydes; moreover, the phototoxicity of these compounds has been tested on a cultured cell line of murine fibroblast.

Method of preparing photochemotherapic alkylangelicin compounds

The alkylangelicins according to the invention are obtained starting from an umbelliferone, in which the 6-position is already substituted by an alkyl group; in such a way the 7-allyloxy or 7-acyloxy umbelliferone intermediates can form by transposition of the allyl or acyl group only the 8-allyl and 8-acyl derivatives, and therefore the presence, even in traces, of psoralens is absolutely excluded in the subsequent synthetic steps. The 6-alkylangelicins thus obtained are particularly usable for the photochemotherapy of psoriasys and of other skin diseases characterized by cellular hyperproliferation, as well as for the photochemotherapy of vitiligo and of alopecia aerata.

Photochemotherapic method of treating psoriasis by using methylangelicin compounds

The alkylangelicins according to the invention are obtained starting from an umbelliferone, in which the 6-position is already substituted by an alkyl group; in such a way the 7-allyloxy or 7-acyloxy umbelliferone intermediates can form by transposition of the allyl or acyl group only the 8-allyl and 8-acyl derivatives, and therefore the presence, even in traces, of psoralens is absolutely excluded in the subsequent synthetic steps. The 6-alkylangelicins thus obtained are particularly usable for the photochemotherapy of psoriasys and of other skin diseases characterized by cellular hyperproliferation, as well as for the photochemotherapy of vitiligo and of alopecia aerata.

Synthesis of some photosensitizing methylangelicins, as monofunctional reagents for DNA

angelicins methylated angelicans were synthesized for obtaining monofunctional reagents for DNA; these compounds may present some interest with regard to the development of useful drugs in photochemotheapy. The new derivatives photobind covalently to DNA, however, they are unable to produce inter-strand, cross-linkages in the macromolecule. Thephotobiological activity was tested on phage T2 and was higher for the methylated derivatives than for angelicin.