19492-11-6Relevant articles and documents
Synthesis of 2-acylated and sulfonated 4-hydroxycoumarins: In vitro urease inhibition and molecular docking studies
Rashid, Umer,Rahim, Fazal,Taha, Muhammad,Arshad, Muhammad,Ullah, Hayat,Mahmood, Tariq,Ali, Muhammad
, p. 111 - 116 (2016)
Sixteen 4-hydroxycoumarin derivatives were synthesized, characterized through EI-MS and 1H NMR and screened for urease inhibitory potential. Three compounds exhibited better urease inhibition than the standard inhibitor thiourea (IC50 = 21 ± 0.11 μM) while other four compounds exhibited good to moderate inhibition with IC50 values between 29.45 ± 1.1 μM and 69.53 ± 0.9 μM. Structure activity relationship was established on the basis of molecular docking studies, which helped to predict the binding interactions of the most active compounds.
Synthesis and photooxygenation of furo[3,2-c]coumarin derivatives as antibacterial and DNA intercalating agent
Al-Sehemi, Abdullah G.,El-Gogary, Sameh R.
, p. 316 - 320 (2012/04/23)
Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2- c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Syntheses of 2,3-dimethyl-4H-furo[3,2-c]coumarin and 3-phenyl-4H-furo[3,2-c]coumarin as angular furocoumarins were carried out through Williamson reaction of 4-hydroxycoumarin with α-haloketones followed by cyclization. Photooxygenation of the synthesized furocoumarin derivatives was performed and the photoproducts were isolated and characterized. The affinity of 2,3-dimethyl-4H-furo[3,2-c]coumarin towards DNA and the antibacterial activity were evaluated and compared with 8-methoxypsoralen (8-MOP). Copyright
Functionalized 4-hydroxy coumarins: Novel synthesis, crystal structure and DFT calculations
Stefanou, Valentina,Matiadis, Dimitris,Melagraki, Georgia,Afantitis, Antreas,Athanasellis, Giorgos,Igglessi-Markopoulou, Olga,McKee, Vickie,Markopoulos, John
, p. 384 - 402 (2011/03/22)
A novel short-step methodology for the synthesis in good yields of functionalized coumarins has been developed starting from an activated precursor, the N-hydroxysuccinimide ester of O-acetylsalicylic acid. The procedure is based on a tandem C-acylation-c
Novel short-step synthesis of functionalized γ-phenyl-β- hydroxybutenoates and their cyclization to 4-hydroxycoumarins via the N-hydroxybenzotriazole methodology
Athanasellis, Giorgos,Melagraki, Georgia,Chatzidakis, Haralambos,Afantitis, Antreas,Detsi, Anastasia,Igglessi-Markopoulou, Olga,Markopoulos, John
, p. 1775 - 1782 (2007/10/03)
A novel method for the synthesis of functionalized 3-substituted 4-hydroxycoumarins is reported. C-Acylation compounds were derived from the reaction of the N-hydroxybenzotriazole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title compounds. The synthesis is simple and the compounds are produced in yields varying from 39 to 80%. The structure of the newly prepared C-acylation compounds was thoroughly studied through NMR spectroscopy for the first time in the literature.
Efficient synthesis of trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives from 4-hydroxycoumarin
Liao, Yuan-Xiu,Kuo, Pei-Yu,Yang, Ding-Yah
, p. 1599 - 1602 (2007/10/03)
Various trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives have been synthesized from 4-hydroxycoumarin with a 30-40% yield over six steps. The key step of the synthesis is a base-promoted intramolecular cyclization of enamines 5, followed by dehydration to generate the fused pyrrole ring.
Synthesis and reactions of 3-aroyl derivatives of 4-hydroxy-2-quinolones and 4-hydroxycoumarin
Kappe, Thomas,Schnell, Barbara
, p. 663 - 670 (2007/10/03)
3-Aroyl-4-hydroxy-2-quinolones 4 and 11 can be synthesized starting with 1 or 9 via Fries rearrangement of the corresponding esters 3 and 10, catalyzed by potassium cyanide and 18-crown-6. A one pot procedure is presented in which the esters do not need to be isolated. Reduction of the aryl ketones 4 and 11 with zinc dust leads to the benzyl derivatives 5 and 12. Reaction of the aryl ketones 4 and 11 with hydroxylamine and subsequent heating of the crude product leads via thermal Beckmann rearrangement and dehydration to oxazoloquinolones 7 and 14. 2-Aroyloxypyrido[1,2-a]pyrimidin-4-ones 17 and 20 could not be converted to the corresponding ketones by Fries rearrangement.
NOUVEAU MODE DE CYCLYSATION DE CETO-YLURES. APPLICATION A UNE SYNTHESE IGINALE D'ACYL-3 HYDROXY-4-COUMARINES ET DE L'HYDROXY-11 BENZO-(b) 12 XANTHONE-12
Babin, P.,Dunogues, J.,Petraud, M.
, p. 1131 - 1139 (2007/10/02)
The thermal decomposition of keto-ylides resulting from the reaction of m- and p-acetoxy benzoyl chlorides with Ph3P=CH-COOMe leads, after saponification to m- and p-phenylpropiolic acid respectively.Ortho substitution by an acyl group generally changes the orientation of the reaction.Thus o-acetoxy-, benzoyloxy- or phenylacetoxy benzoyl chlorides respectively afford: and (R=Me,Ph) in satisfactory yields.Saponification of the first and second ones gives: (R=Me, Ph).This constitutes a new, convenient route to 3-acyl 4-hydroxy cumarins and 11-hydroxy 12H-benzoxanthene 12-one.Formation of these last products involves the carbonyl of the acyloxy-substituent and not of the acyl chloride as previously observed in these series.
