92646-98-5Relevant academic research and scientific papers
Mannich bases of hydroxycoumarins: Synthesis, DFT/QTAIM computational study and assessment of biological activity
Castro, María Eugenia,Durand-Niconoff, J. Sergio,Fernández-Pomares, Cynthia,Guerrero, Tomás,Juárez-Aguilar, Enrique,Melendez, Francisco J.,Montoya-Hernández, Eva Luz,Olivares-Romero, José L.,Ortiz-Blanco, Erik,Sosa-Ortiz, Gabriela,Tovar-Miranda, Ricardo
, p. 31260 - 31271 (2021/11/30)
The synthesis of six Mannich bases derived from hydroxycoumarins was carried out in moderate yields, two of these derivatives were described for the first time. Conformational analysis was performed through DFT theoretical calculations explaining the formation of stable six membered rings based on intramolecular hydrogen bonds within the structure. These findings were correlated with the antiproliferative activity. The biological activity of the Mannich bases through their antiproliferative activity in the HeLa cancer cell line is described for the first time, showing that the compounds were able to inhibit proliferation in cervical cancer by more than 60%. Likewise, the theoretical modeling of the photophysical properties was realized with promising results, showing that the HOMO-LUMO energies of the new compounds present the lowest electronic gap values for those with donor groups in their structure, which makes them potential fluorophores. This journal is
Establishing a flow process to coumarin-8-carbaldehydes as important synthetic scaffolds
Zak, Jaroslav,Ron, David,Riva, Elena,Harding, Heather P.,Cross, Benedict C. S.,Baxendale, Ian R.
supporting information; experimental part, p. 9901 - 9910 (2012/09/07)
Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin-8-carbaldehydes are lacking. We describe here a high-yielding continuous flow synthesis that requires no manual intermediate purification or work-up, giving access to multigram quantities of the aldehyde product. Aldehyde on tap: Despite their usefulness as fluorophores and synthetic precursors, efficient and reliable routes to coumarin-8- carbaldehydes are lacking. A high-yielding continuous flow synthesis that requires no manual intermediate purification or work-up is described, giving access to multigram quantities of aldehyde product (see scheme). Copyright
Claisen rearrangement of 3-bromo-, 3,6-dibromo-, 3,8-dibromo- and 8- iodo/aminomethyl/acetyl-7-allyloxy-4-methylcoumarins
Ghantwal,Samant
, p. 1242 - 1247 (2007/10/03)
7-Hydroxy-4-methylcoumarin 1 has been brominated under different conditions to obtain the corresponding 3-bromo-2; 3,6-dibromo- 4; 3,8- dibromo- 3; and 3,6,8-tribromo- 8 derivatives. The 24 are allylated and subjected to Claisen rearrangement in N,N-DMA when only 8-allyl-7-hydroxy-4- methylcoumarin 13 is obtained. The Claisen rearrangement of 8-iodo and 8- aminomethyl coumarins also give 13. In all these rearrangements the 8- substituent is removed and the migration takes place at the 8-position. The N,N-DMA serves as the scavenger for the substituent lost. The Claisen rearrangement of 8-acetyl-7-allyloxy-4-methylcoumarin gives 8-acetyl-6-allyl- 7-hydroxy-4-methylcoumarin, in which the acetyl group remains intact.
