3779-03-1

Usage

Uses

Used in Insect Control:
9-METHOXY-2,3-DIHYDROFURO[3,2-G]COUMARIN is used as an insect antifeeding agent for its ability to deter insects from feeding on treated plants. This property makes it a valuable tool in agriculture for protecting crops from insect damage.
Used in Pharmaceutical Industry:
9-METHOXY-2,3-DIHYDROFURO[3,2-G]COUMARIN is used as a dihydro impurity and a metabolite of 8-Methoxypsoralen (M260795), also known as Methoxsalen. 9-METHOXY-2,3-DIHYDROFURO[3,2-G]COUMARIN has potential applications in the development of new drugs, particularly in the treatment of various medical conditions.
Used in Research and Development:
Due to its unique chemical structure and biological activities, 9-METHOXY-2,3-DIHYDROFURO[3,2-G]COUMARIN can be used as a research compound for studying the properties and potential applications of furocoumarin derivatives in various fields, including pharmaceuticals, agriculture, and materials science.

InChI:InChI=1/C12H10O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-3,6H,4-5H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 68123-30-8 Dihydro-8-hydroxypsoralen 
• 298-81-7 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one 
• 6272-27-1 6,7-dihydroxybenzofuran-3[2H]-one 
• 42484-95-7 2,3-dihydro-benzofuran-6,7-diol 

Downstream Products

• 1930-59-2 4',5'-Dihydro-5-amino-8-methoxypsoralen 

Relevant academic research and scientific papers

Synthetic models related to methoxalen and menthofuran-cytochrome P450 (CYP) 2A6 interactions. Benzofuran and coumarin derivatives as potent and selective inhibitors of CYP2A6

Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 μM and 1.27 μM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 μM) and coumarin (5-methoxycoumarin: IC50=0.13 μM and 6-methoxycoumarin: IC50=0.64 μM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

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.

Reduced and quaternized psoralens as photo-activated therapeutics

The invention features phototherapeutic compositions comprising Type 1, Type 2, or Type 3 psoralens and methods of using such compounds for treatment of proliferative diseases of skin, blood and bone marrow.

7-alkoxycoumarins, dihydropsoralens, and benzodipyranones as photo-activated therapeutic agents and inhibitors of epidermal growth factor

A photochemotherapeutic compound of the formula STR1 wherein (i) n is zero, W is a (C1-16) alkyl, alkenyl, or alkynyl linear or branched chain hydrocarbon, having no more than four O, N, or S atoms in or attached to the chain; or (ii) n is 1, W is CR or CR2, and R, R', and R" are independently H or CH3 ; or (iii) N is 2, W is CR or CR2, and R, R', and R" are independently H or CH3 ; and A, B, C, and D are independently selected from hydrogen, alkyl, aryl, halogen, amino, aminoalkyl, nitro, alkoxy, aryloxy, hydroxy, carboxy, haloalkyl, or haloalkoxy, particularly compounds of the foregoing structure in which W is a charged substiuent and n=0 or 1.