523-50-2 Usage
Uses
Used in Antifungal Applications:
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran is used as an antifungal agent for its ability to inhibit the growth and proliferation of various fungi, which can be beneficial in treating fungal infections and controlling the spread of fungal pathogens.
Used in Pharmaceutical Industry:
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran is used as a pharmaceutical compound for its antibacterial properties, as it can help combat a number of Gram (+) and Gram (-) bacteria. This makes it a potential candidate for the development of new antibiotics to address the growing issue of antibiotic resistance.
Used in Hepatoprotective Applications:
In the pharmaceutical industry, 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran is also used as a hepatoprotective agent, as it has been shown to prevent tacrine-induced cytotoxicity in human liver-derived HepG2 cells. This property could be harnessed to develop treatments for liver diseases and conditions where hepatoprotection is necessary.
Used in Cardiovascular Applications:
2-Oxo-(2H)-furo(2,3-h)-1-benzopyran is used as a cardiovascular agent for its ability to induce vascular relaxation in phenylephrine-precontracted rat aorta. This characteristic suggests potential applications in the development of drugs targeting hypertension and other cardiovascular conditions.
Used in Anticancer Research:
In the field of oncology, 2-Oxo-(2H)-furo(2,3-h)-1-benzopyran is used as a compound for further research and development, due to its weak inhibition of topoisomerase II. This property may lead to the discovery of new anticancer drugs or contribute to the understanding of cancer cell mechanisms.
Synthesis
Iodination of commercially available umbelliferone (7-hydroxycoumarin) yields 7-hydroxy-8-iodocoumarin. Acetoxy group can be introduced into hydroxyl of 7-hydroxy-8-iodocoumarin, which is used to create vaginol or vaginidiol with an isopropyl Grignard reagent and commercially available epoxy aldehydes. Subsequent acid-catalysed fragmentation of vaginol with dichloromethane in trifluoroacetic acid yields angelicin.
Toxicity
The LD50 of angelicin is 322 mg/kg which shows acute toxicity if orally administered to rats. The possible consequences are alteration in circadian rhythm and righting reflex, ataxia and analgesia.
Synthesis Reference(s)
Tetrahedron, 51, p. 3087, 1995 DOI: 10.1016/0040-4020(95)00070-O
Clinical Use
Angelicin derivatives are used to treat psoriasis and cancer. One way of treating these diseases is by photochemotherapy (PUVA) which combines UV irradiation with photosensitizing chemical. Also, it was shown that it is actively inhibits the synthesis of nucleic acids in tumor cells thereby decreasing their growth.
Check Digit Verification of cas no
The CAS Registry Mumber 523-50-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 3 respectively; the second part has 2 digits, 5 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 523-50:
(5*5)+(4*2)+(3*3)+(2*5)+(1*0)=52
52 % 10 = 2
So 523-50-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
523-50-2Relevant academic research and scientific papers
Synthesis of 2,3-dihydro-3-hydroxy-2-hydroxylalkylbenzofurans from epoxy aldehydes. One-step syntheses of brosimacutin G, vaginidiol, vaginol, smyrindiol, xanthoarnol, and avicenol A. Biomimetic syntheses of angelicin and psoralen
Zou, Yefen,Lobera, Mercedes,Snider, Barry B.
, p. 1761 - 1770 (2007/10/03)
(Chemical Equation Presented) We have developed two practical one-step syntheses of 2,3-dihydro-3-hydroxy-2-hydroxyalkylbenzofurans from readily available optically pure α,β-epoxy aldehydes. Electron-deficient resorcinols react with epoxy aldehydes using either Cs2CO3 in DMF or KOH/CaCl2 in MeOH to give adducts 13, 16, 18, 20, 21, and brosimacutin G (6t). Grignard reagents prepared by low-temperature halogen-metal exchange of acetoxy iodocoumarins 35d and 40 and acetoxy bromonaphthalene 41 add to epoxy aldehyde (S)-26 to complete the first syntheses of vaginidiol (7c), vaginol (7t), smyrindiol (8c), xanthoarnol (8t), and avicenol A (9t). Acid-catalyzed fragmentation of vaginidiol or vaginol provides angelicin, while that of smyrindiol or xanthoarnol affords psoralen. In both cases, the trans isomers fragment only twice as fast as the cis isomers, possibly through the intermediacy of a common benzylic cation. This may have implications for the biosynthesis of angelicin and psoralen.
A convenient synthesis of psoralens
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Viola, Giampietro,Vedaldi, Daniela,Dall'Acqua, Francesco
, p. 4859 - 4863 (2007/10/03)
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.
