New synthetic routes to furocoumarins and their analogs: a review.

Many furocoumarins and their analogs possess a prominent photobiological activity. Some of them are successfully used as drugs in phototherapy of skin diseases. Fries rearrangement of acyloxyheteroarenes, condensation of acylhydroxyheteroarenes with alpha-carbonyl compounds under base catalysis and transformations of dihydrofurocoumarinones are new trends in synthesis of furocoumarins and their analogs.

• Publication year

  2004

• Venue

  Molecules

• Publication date

  2004-02-28

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.3390/90300050PMID 18007411PMCID PMC6147435
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• Fries rearrangement of acyloxyheteroarenes, base-catalyzed condensation of acylhydroxyheteroarenes with alpha-carbonyl compounds, and transformations of dihydrofurocoumarinones are highlighted as new trends in the synthesis of furocoumarins and their analogs.

  Confidence 0.96

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review

• acylhydroxyheteroarenes

  substrate classes

  Heteroaromatic compounds containing both acyl and hydroxy groups that serve as precursors in the condensation route.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• acyloxyheteroarenes

  substrate classes

  Heteroaromatic substrates bearing an acyloxy substituent that undergo the rearrangement route described in the abstract.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• alpha-carbonyl compounds

  substrate classes

  Carbonyl compounds with an activated alpha position that react in the base-catalyzed condensation route.

  Aliases: α-carbonyl compounds

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• base catalysis

  reaction conditions

  Base-promoted reaction conditions used to drive the condensation transformations mentioned in the abstract.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• dihydrofurocoumarinones

  compound classes

  Partially hydrogenated furocoumarinone derivatives that are transformed in one of the synthetic approaches discussed.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• fries rearrangement

  reactions

  An acyl migration rearrangement used here as one of the synthetic routes to furocoumarin-related compounds.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review
• furocoumarins

  compound classes

  A class of furan-fused coumarin compounds discussed as the main synthesis targets in the review.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewGahyoun (29ua5897xm) reviewAnonymous (12632b8b5f) review

• New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: synthesis, DNA interaction, and antiproliferative activity.

  1999cited by this paper
• CHOLESTERYL ESTERS OF FUROCOUMARIN AND COUMARIN CARHOXYLIC ACIDS

  1999cited by this paper
• THE FIRST PYRROLOFUROCOUMARINS

  1999cited by this paper
• Synthesis and biological activity of (hydroxymethyl)- and (diethylaminomethyl)benzopsoralens.

  1999cited by this paper
• A REGIOSELECTIVE SYNTHESIS OF 6-ARYLAZO-7-HYDROXYCOUMARINS AND 5'- ARYLAZOPSORALENS.

  1998cited by this paper
• UNUSUAL ONE-POT "SUBSTITUTION" OF 3- ACETYL AND 3- ETHOXYCARBONYL FUNCTIONS FOR CYANO GROUP IN COUMARINS

  1998cited by this paper
• The first synthesis of furocoumarin dimers

  1998cited by this paper
• Unusual transformation of 4-methyldihydrofuro[2,3-h]coumarin-9-one oxime in presence of Beckmann rearrangement catalysts

  1997cited by this paper
• THE BASE-CATALYZED CYCLIZATION OF ACYLMETHYL ETHERS OF 7-HYDROXYCOUMARINS

  1997cited by this paper
• A New Short Way to Furocoumarins

  1996cited by this paper
• Synthesis and antiproliferative activity of furocoumarin isosters.

  1995cited by this paper
• New Methods of Synthesis of 4-Methylangelicin

  1995cited by this paper
• Photosensitized cross-linking and cleavage of pBR322 and M13 DNA: comparison of 4,4',6-trimethylangelicin and 3-carbethoxypsoralen.

  1994cited by this paper
• Biophysical and biological properties of newly synthesized dioxinocoumarin derivatives. II. Dark and photoinduced effects on T7 phage, yeast and HeLa cells.

  1994cited by this paper
• 8-Azapsoralen derivatives: isolation and characterization of the furan-side cycloadducts with DNA.

  1994cited by this paper
• Crosslinking and cleavage of pBR322 DNA photosensitized by 7-methylpyrido[3,4-c]psoralen.

  1994cited by this paper
• A New Synthesis of 3-Phenyl-5,6-Dihydropyridin-2(1 H)-ones

  1993cited by this paper
• Photopheresis: present and future aspects.

  1991cited by this paper
• Deprotonation of 1,2,3,4,5-Pentamethylrhodocenium; a New Route to 1-Substituted-2,3,4,5-tetramethylcyclopentadienylrhodium Complexes

  1991cited by this paper
• Methylangelicins: structure activity studies on the role of methyl groups present in 3,4 and 4',5' photoreactive sites.

  1991cited by this paper
• Molecular mechanics and dynamics of DNA-furocoumarin complexes: effect of the aromatization of the pyrone ring on the intercalation geometry.

  1990cited by this paper
• 6-Methylangelicins: a new series of potential photochemotherapeutic agents for the treatment of psoriasis.

  1984cited by this paper
• 4'-Methylangelicins: new potential agents for the photochemotherapy of psoriasis.

  1983cited by this paper
• The Natural Coumarins : Occurrence

  1982cited by this paper
• The natural coumarins : occurrence, chemistry, and biochemistry

  1982cited by this paper
• New monofunctional reagents for DNA as possible agents for the photochemotherapy of psoriasis: derivatives of 4,5'-dimethylangelicin.

  1981cited by this paper
• Methylangelicins: new potential agents for the photochemotherapy of psoriasis. Structure-activity study on the dark and photochemical interactions with DNA.

  1981cited by this paper
• 4,5‘‐DIMETHYLANGELICIN: A NEW DNA‐PHOTOBINDING MONOFUNCTIONAL AGENT *

  1979cited by this paper
• Zh. Obshch. Khim.

  1975cited by this paper

• Synthesis of new condensed naphthoquinone, pyran and pyrimidine furancarboxylates

  2025cites this paper
• Recent Advances on Sustainable Synthesis of Furocoumarins

  2024cites this paper
• Heraclenin promotes the osteogenic differentiation of bone marrow stromal cells by activating the RhoA/ROCK pathway.

  2024cites this paper
• Research Progress on the Synthesis and Biological Activity of Coumestan Natural Products

  2024cites this paper
• Recent advances in the synthesis and applications of furocoumarin derivatives

  2023cites this paper
• A convenient synthesis of furo[3,2-c]pyran-3-carboxylates from 3-bromo-3-nitroacrylates

  2022cites this paper
• Experimental studies on the corrosion inhibition performance of chalcone derivative for mild steel in acid and alkaline solution

  2022cites this paper
• Metal-catalyzed routes for the synthesis of furocoumarins and coumestans

  2021cites this paper
• 2-(2-(4-Methoxyphenyl)-4,9-dimethyl-7-oxo-7H-furo[2,3-f]chromen-3-yl)acetic Acid

  2021cites this paper
• Synthesis of 8-carbo substituted 2-(trifluoromethyl)-4H-furo[2,3-h]chromen-4-ones and their thienoangelicin derivatives

  2020cites this paper
• Organocatalytic 1,4-Addition of Azadienes with 3-Homoacyl Coumarins toward Highly Enantioenriched Benzofuran Coumarin Skeletons.

  2020cites this paper
• Imperatorin as a Promising Chemotherapeutic Agent against Human Larynx Cancer and Rhabdomyosarcoma Cells

  2020cites this paper
• Furanocoumarins in anticancer therapy - For and against.

  2020cites this paper
• Synthesis of Some Hybrid 7-Hydroxy Quinolinone Derivatives As Anti Breast Cancer Drugs

  2019cites this paper
• Coumarins from Creston Apple Seeds: Isolation, Chemical Modification, and Cytotoxicity Study

  2018cites this paper
• FeCl3 or MeSO3H-promoted multicomponent reactions for facile synthesis of structurally diverse furan analogues.

  2018cites this paper
• Identification of a Pyranocoumarin Photosensitizer that is a Potent Inhibitor of Keratinocyte Growth

  2018cites this paper
• SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL COUMARIN DERIVATIVES AS POTENTIAL ANTIMICROBIAL AGENTS

  2016cites this paper
• DESIGN, SYNTHESIS AND BIOLOGICAL EVALUATION OF SOME NEW SUCCINIMIDE, 2-IMINOTHIAZOLINE AND OXAZINE DERIVATIVES BASED BENZOPYRONE AS ANTICONVULSANT AGENTS

  2016cites this paper
• SYNTHESIS AND BIOLOGICAL EVALUATION OF NOVEL COUMARIN DERIVATIVES AS POTENTIAL ANTIMICROBIALs AGENTS Original Article

  2016cites this paper
• DMSO and iodine mediated reaction of 4-hydroxycoumarins and aldehydes/aryl methyl ketones: synthesis of furo[3,2-c]coumarins

  2016cites this paper
• Organobase catalysis using 1-(2-pyrimidyl)piperazine in micellar medium: an approach for better performance and reusability of organobase

  2016cites this paper
• Recent advances and perspectives in the synthesis of bioactive coumarins

  2016cites this paper
• Synthesis and Characterization of New heterocycles compounds derived from coumarin

  2016cites this paper
• Coumarin heterocyclic derivatives: chemical synthesis and biological activity.

  2015cites this paper
• Crystal structure of 4-methoxyphenyl 2-oxo-2H-chromene-3-carboxylate

  2015cites this paper
• New insights into the chemistry and antioxidant activity of coumarins.

  2014cites this paper
• Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents.

  2013cites this paper
• Synthesis and biological evaluation of novel formyl-pyrazoles bearing coumarin moiety as potent antimicrobial and antioxidant agents.

  2013cites this paper
• The Reaction of Ethyl 2-oxo-2H-chromene-3-carboxylate with Hydrazine Hydrate

  2013cites this paper
• Novel synthesis of substituted furo[3,2-c]chromen-4-ones via four-component reaction from substituted nitrostyrenes, aromatic aldehydes, coumarins, and ammonium acetate.

  2013cites this paper
• Total syntheses of the coumarin-containing natural products pimpinellin and fraxetin using Au(I)-catalyzed intramolecular hydroarylation (IMHA) chemistry.

  2013cites this paper
• Palladium-catalyzed intramolecular hydroarylation of 4-benzofuranyl alkynoates. Approach to angelicin derivatives.

  2012cites this paper
• PALLADIUM-CATALYZED INTRAMOLECULAR HYDROARYLATION OF 6-BENZOFURANYL ALKYNOATES (Dedicated to Professor Dr. Ei-ichi Negishi on the occasion of his 77th birthday)

  2012cites this paper
• An efficient, mild and scalable synthesis of bioactive compounds containing the angelicin scaffold

  2012cites this paper
• Expeditious Entry to Novel 2-Methylene-2,3-dihydrofuro[3,2-c]chromen-2-ones from 6-Chloro-4-hydroxychromen-2-one and Propargylic Alcohols

  2011cites this paper
• Discrimination analysis of human lung cancer cells associated with histological type and malignancy using Raman spectroscopy.

  2010cites this paper
• Prognostic value of aspartyl (asparaginyl)-beta-hydroxylase/humbug expression in non-small cell lung carcinoma.

  2009cites this paper
• Formulation and evaluation of epoxides derived from oxygen heterocyclic compounds and indane-1, 3-diones as possible specific targeting agents for cytotoxic activity.

  2008cites this paper
• Tricyclic Systems: Central Carbocyclic Ring with Fused Five- and Six-membered Rings

  2008cites this paper
• Study of acyl group migration by femtosecond transient absorption spectroscopy and computational chemistry.

  2007cites this paper
• Synthesis and reactions of some new allyl furobenzopyranone derivatives

  2007cites this paper
• New Synthetic Routes to Furocoumarins and Their Analogues

  2004cites this paper