71386-91-9Relevant academic research and scientific papers
Pd/pivalic acid mediated direct arylation of 2-pyrones and related heterocycles
Pardo, Leticia M.,Prendergast, Aisling M.,Nolan, Marie-T.,Muimhneachin, Eoin,McGlacken, Gerard P.
, p. 3540 - 3550 (2015)
Abstract Direct arylation represents a favourable alternative to traditional cross-coupling reactions and has found widespread use with simple aryls and robust heterocycles. Herein a direct arylation protocol has been optimised and applied to more delicat
Synthesis and cytotoxic activity of non-naturally substituted 4-oxycoumarin derivatives
Serra, Silvia,Delogu, Giovanna,Casu, Laura,Vazquez-Rodriguez, Saleta,Santana, Lourdes,Uriarte, Eugenio,Chicca, Andrea,Gertsch, Juerg
, p. 5791 - 5794,4 (2020/07/31)
Coumarins are a large family of natural and synthetic compounds exerting different pharmacological effects, including cytotoxic, anti-inflammatory or antimicrobial. In the present communication we report the synthesis of a series of 12 diversely substituted 4-oxycoumarin derivatives including methoxy substituted 4-hydroxycoumarins, methyl, methoxy or unsubstituted 3-aryl-4-hydroxycoumarins and 4-benzyloxycoumarins and their anti-proliferative effects on breast adenocarcinoma cells (MCF-7), human promyelocytic leukemia cells (HL-60), human histiocytic lymphoma cells (U937) and mouse neuroblastoma cells (Neuro2a). The most potent bioactive molecule was the 4-hydroxy-5,7- dimethoxycoumarin (compound 1) which showed similar potency (IC50 0.2-2 μM) in all cancer cell lines tested. This non-natural product reveals a simple bioactive scaffold which may be exploited in further studies.
The reactivity of 4-hydroxycoumarin under heterogeneous high-intensity sonochemical conditions
Cravotto, Giancarlo,Nano, Gian Mario,Palmisano, Giovanni,Tagliapietra, Silvia
, p. 1286 - 1291 (2007/10/03)
High-intensity ultrasounds have been employed in the synthesis of 4-hydroxycoumarin derivatives, using mainly water as reaction medium. Marked improvements of reaction rates, chemoselectivity and product yields have been observed on comparing sonochemical with ordinary conditions. In the alkylation of a series of allyl and benzyl bromides a pathway switch occured to yield 3-alkyl-4-hydroxycoumarin derivatives.
Phase-transfer catalysed alkylation of 4-hydroxycoumarin - Synthesis of α,α-disubstituted o-hydroxyacetophenones
Majumdar,Khan,Chattopadhyay
, p. 483 - 485 (2007/10/02)
Phase-transfer catalysed alkalyation of 4-hydroxycoumarin (1) with active halides give O-alkylated products, 2 (20-60%), C, O-dialkylated products, 3 (15-20%) and α,α-disubstituted-o-hydroxyacetophenones, 5 (20-75%). Only in one case C,C-dialkylated product, 4 (35%) has been obtained.
