1930-56-9

Upstream product

• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 482-44-0 imperatorin 
• 2009-24-7 8-hydroxypsoralen 
• 87-66-1 2-hydroxyresorcinol 
• 29267-67-2 2-methoxyresorcinol 
• 485-90-5 hydrangetin 
• 1930-54-7 4-bromo-9-methoxy-7H-furo[3,2-g]chromen-7-one 

Downstream Products

• 49739-65-3 4-amino-9-methoxy-7H-furo<3,2-g><1>benzopyran-7-one 
• 1930-59-2 4',5'-Dihydro-5-amino-8-methoxypsoralen 
• 86885-06-5 5-hydroxy-4-methoxy-1,2,6,7-tetrahydro-9H-furo<2,3-h>quinolin-8-one 
• 75-07-0 acetaldehyde 
• 101884-35-9 4-(benzylideneamino)-9-methoxy-7H-furo[3,2-g]chromen-7-one 
• 102545-49-3 6-bibenzyl-α-yl-5-bromo-7,8-dihydroxy-coumarin 
• 7471-59-2 2-bromo-4,6-dihydroxy-5-methoxy-isophthalaldehyde 
• 7504-52-1 8-methoxy-5-bromo-thiopsoralen 
• 1930-54-7 4-bromo-9-methoxy-7H-furo[3,2-g]chromen-7-one 
• 7471-73-0 5-hydroxy-8-methoxypsoralen 
• 7471-72-9 5-Chloro-9-methoxy-7H-furo<3,2-g><1>benzopyran-7-one 

Relevant academic research and scientific papers

Electronic Finetuning of 8-Methoxy Psoralens by Palladium-Catalyzed Coupling: Acidochromicity and Solvatochromicity

Differently 5-substituted 8-methoxypsoralens can be synthesized by an efficient synthetic route with various cross-coupling methodologies, such as Suzuki, Sonogashira and Heck reaction. Compared to previously synthesized psoralens, thereby promising daylight absorbing compounds as potentially active agents against certain skin diseases can be readily accessed. Extensive investigations of all synthesized psoralen derivatives reveal fluorescence in the solid state as well as several distinctly emissive derivatives in solution. Donor-substituted psoralens exhibit remarkable photophysical properties, such as high fluorescence quantum yields and pronounced emission solvatochromicity and acidochromicity, which were scrutinized by Lippert–Mataga and Stern–Volmer plots. The results indicate that the compounds exceed the limit of visible light, a significant factor for potential applications as an active agent. In addition, (TD)DFT calculations were performed to elucidate the underlying electronic structure and to assign experimentally obtained data.

Structural modifier of 8-methoxypsoralen as well as preparation method and application of structural modifier

The invention discloses a structural modifier of 8-methoxypsoralen as well as a preparation method and application of the . The structural modifier of the 8-methoxypsoralen provided by the invention is a compound B20 shown as a formula 1 or a compound A10 shown as a formula 2. The bacteriostatic activity of the compound B20 for enterotoxigenic escherichia coli at the concentration of 64 mu g/mL is2.3 times of that of the 8-methoxypsoralen; the bacteriostatic activity of the compound A10 for enterotoxigenic escherichia coli at the concentration of 64 mu g/mL is 2.4 times of the 8-methoxypsoralen. The compound B20 and the compound A10 can be applied to the preparation of a medicament for treating and/or preventing piglet diarrhea. The formula 1 and the formula 2 are shown in the description.

Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents

A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 μM, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.

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.

Alkoxypsoralens, novel nonpeptide blockers of Shaker-type K+ channels: Synthesis and photoreactivity

A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8- Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

SYNTHESIS OF FUROCOUMARIN DERIVATIVES LIKELY TO POSSESS ANTIMICROBIAL ACTIVITY

The reaction of fuming nitric acid with bergapten (I) and xanthotoxin (II) afforded the corresponding nitro derivatives (IV and V respectively). With imperatorin (III) the reaction was found to be oxidation rather than nitration, and a nitrogen-free compound (VII) resulted. Molecular bromine reacted with bergapten (I) to afford three products (VIIIa - c) in a mixture, and with xanthotoxin (II) to produce the 5-bromo derivative (IX). Anomalously, molecular bromine reacted with imperatorin (III) to give the phenolic compound 5-bromo-9-hydroxy-furo(3,2-g)-coumarin (X). Structures of all products (VI - X) were confirmed by IR, 1H-NMR and mass spectral data.