14159-13-8

Upstream product

• 24416-64-6 4',5'-dihydro-4-methyl psoralene 
• 1616-53-1 6-allyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 
• 100953-18-2 2-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]acetaldehyde 
• 13196-11-7 6-hydroxybenzofuran 
• 141-97-9 ethyl acetoacetate 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 91963-63-2 2-<(4-methyl-2-oxo-2H-7-chromenyl)oxy>ethanol 
• 96853-35-9 5-Hydroxy-2-(2-nitroethenyl)-phenol 
• 96853-42-8 4-(2-Nitroethyl)benzene-1,3-diol 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 74794-30-2 7-hydroxy-8-iodo-4-methyl-2H-1-benzopyran-2-one 
• 76463-90-6 7-allyloxy-8-iodo-4-methyl-2H-1-benzopyran-2-one 
• 85878-59-7 6-acetoxy-2,3-dihydrobenzofuran 
• 108-46-3 recorcinol 

Relevant academic research and scientific papers

Concise and efficient synthesis of linear furocoumarins: Psoralen and 4-methylpsoralen

A method for the rapid synthesis of psoralen and 4-methylpsoralen has been developed. The key intermediates, coumarinyloxyaldehydes, were obtained in only two steps from the easily available starting materials, 7-hydroxycoumarin derivatives, by an oxidative procedure. By using Swern oxidation, psoralen and 4-methylpsoralen were finally produced in the overall yields of 71% and 67%, respectively. Copyright Taylor & Francis Group, LLC.

Synthesis and Activity of New Schiff Bases of Furocoumarin

Furocoumarins, such as 8-MOP, are the most common medications used to relieve the symptoms of vitiligo clinically. Some furocoumarins also showed excellent performance in an anti-bacterial assay. This paper describes the synthesis of a series of novel Schiff bases (6a-6k), and their promotion in melanogenesis and anti-bacterial properties were studied in vitro. The pigment production of B16 cells and bacterial inhibition ring assay were applied for the bioactivity of 6a-6k. According to the results, a stronger promotion on pigment content was observed, when six compounds co-cultured with cells, compared with positive control (8-MOP). Significantly, compound 6k (237%) as the most active was found to increase the amount of melanin more than 1.7 times compared with 8-MOP activation rate (136%). All the compounds could moderately retard C. albicans growth. Interestingly, aldehyde 5, which possessed a broader antibacterial spectrum, showed the highest inhibition against C. albicans as well and much better than the positive control (Amphotericin B). Studies of 6k in animal models of vitiligo and related molecular mechanism are presently under way, with the aim of discovering an anti-vitiligo leading compound.

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.

Psoralen schiff base derivatives and application

The invention relates to psoralen schiff base derivatives and an application. The compounds are 4-methyl-7-hydroxycoumarin (which is an intermediate 1), 4-methyl-7-hydroxyethoxycoumarin (which is an intermediate 2), 4-methyl-7-formylmethoxycoumarin (which is an intermediate 3), 5-methyl-7H-furan[3,2-g]benzopyran-7-one (which is a compound 4), 7-oxo-7H-furan[3,2-g]benzopyran-5-formaldehyde (which is a compound 5), and a compound 6a-6k. The fact that the 11 psoralen schiff base derivatives affect generation of melanin in mouse B16 cells and inhibit candida albicans, escherichia coli, and staphylococcus aureus is studied. The resultant compounds 6a-6b, 6d-6f and 6j-6k can be applied to prepare medicines for treating vitiligo in the clinic. The obtained psoralen schiff base derivatives can be used for preparing medicines for treating candida albicans infection in the clinic, and the compounds 6b-6c, 6e-6h and 6h-6k can be used for preparing medicines for treating staphylococcus aureus infection in the clinic.

Psoralen ester derivatives and applications thereof

The invention relates to psoralen ester derivatives and applications thereof; the compounds comprise 4-methyl-7-hydroxy coumarin (an intermediate 1), 4-methyl-7-hydroxyethoxy coumarin (an intermediate 2), 4-methyl-7-formyl methoxy coumarin (an intermediate 3), 5-methyl-7H-furan[3,2-g]benzopyran-7-one (a compound 4), 7-oxo-7H-furan[3,2-g] benzopyran-5-formaldehyde (a compound 5), 5-hydroxymethyl-7H-furan[3,2-g]benzopyran-7-one (a compound 6), (7-oxo-7H-furan[3,2-g]benzopyran-5-yl)methyl acetate (a compound 7) and compounds 8a-8p. The 20 psoralen ester derivatives have influence on generation of melanin in mouse B16 cells and have the inhibitory effect on candida albicans, escherichia coli and staphylococcus aureus. The compounds 4-7, the compounds 8a-8d and the compounds 8k-8o are used for preparation of drugs for treating leucoderma. The obtained psoralen Schiff base derivatives are used for preparation of drugs for treatment of candida albicans infection, and the compound 5 and the compound 7 are also used for preparation of drugs for treatment of staphylococcus aureus infection.

Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study

Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of 1a were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 μg/mL) than 1a (MIC = 6.25 μg/mL), and is even potent than the positive control metronidazole (MIC = 0.50 μg/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of 1a have also led to an outline of structure-activity relationship.

A new efficient method for the total synthesis of linear furocoumarins

A new efficient method for the synthesis of linear furocoumarins by a Nef reaction and intramolecular cyclocondensation in one pot results in the construction of a benzofuran ring. This method provides a new strategy to furnish the benzofuran framework easily, and also allows the convenient synthesis of furocoumarin derivatives with different substituents on the coumarin ring by a subsequent Pechmann reaction. This strategy has also been applied to the preparation of four additional benzofuran derivatives. Georg Thieme Verlag Stuttgart.

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.

Treatment methods for lymes disease and associated debilitating conditions

A method is provided for treating human patients who have Lymes disease by using a psoralen compound, preferably administered in a dosage of 0.3 to 0.7 mg/kg, and activating same either in vitro or in vivo using electromagnetic radiation of a prescribed activating wavelength. The activation of the psoralen compound in the presence of a blood fraction from a patient suffering from Lymes disease produces a composition which will stimulate an effective immune response to the Lymes disease on the part of the patient.

Treatment methods and vaccines for stimulating an immunological response against retroviruses

Human Immunodeficiency Virus infections, particularly AIDS, are treated by administering a psoralen compound which is subsequently activated by exposure to electromagnetic radiation (e.g. UVA light) whereby the activated psoralen compound attacks free virus and/or virus infected cells in the blood of the patient. The treated blood when presented to the patient's immune system engenders an effective immune response against the infection. The method has particular utility in the treatment of ARC patients who have depressed immune function.