55222-57-6Relevant articles and documents
Synthesis of 1-(3H)isobenzofuranone compounds by tin powder promoted cascade condensation reaction
Wang, Shangxian,Wang, Ke-Hu,Chang, Bo,Huang, Danfeng,Hu, Yulai
, (2021/03/31)
An efficient approach for the construction of phthalide compounds is developed through tin powder mediated cascade condensation reaction of 2-formylbenzoic acids with allyl bromides or α-bromoketone under mild reaction conditions. This method is easy to operate and can tolerate various functional groups to give the corresponding phthalides in good to excellent yields. The phthalides produced from α-bromoketone can be further transformed to 3,3a-dihydro-8H-pyrazolo[5, l-a]isoindol-8-one and 8H-pyrazolo[5, l-a]isoindol-8-one.
Synthesis, molecular properties prediction and cytotoxic screening of 3-(2-aryl-2-oxoethyl)isobenzofuran-1(3H)-ones
Da Silva Maia, Angélica Faleiros,Siqueira, Raoni Pais,De Oliveira, Fabrício Marques,Ferreira, Joana Gasperazzo,Da Silva, Silma Francielle,Caiuby, Clarice Alves Dale,De Oliveira, Leandro Licursi,De Paula, Sérgio Oliveira,Souza, Rafael Aparecido Carvalho,Guilardi, Silvana,Bressan, Gustavo Costa,Teixeira, Róbson Ricardo
supporting information, p. 2810 - 2816 (2016/06/08)
In the present investigation, a collection of nineteen 3-(2-aryl-2-oxoethyl)isobenzofuran-1(3H)-ones was synthesized and screened for their cytotoxic activity against a panel of three leukemia cancer cell lines. The compounds were prepared via ZrOCl2·8H2O catalyzed condensation reactions between phthalaldehydic acid and different acetophenones. The reactions were carried out free of solvent and the isobenzofuran-1(3H)-ones were obtained in good yields (80-92%). The identities of the synthesized compounds were confirmed upon IR and NMR (1H and 13C) spectroscopy as well as high resolution mass spectrometry analyses. Structures of compounds 1, 4 and 16 were also investigated by X-ray analysis. The synthesized compounds were submitted to in vitro bioassays against HL-60, K562 and NALM6 cancer cell lines using MTT cytotoxicity assay. After 48 h of treatment, twelve derivatives were able to reduce cell viability and presented IC50 values equal to or below 20 μmol L-1 against at least one of the evaluated lineages. The most active compound corresponded to 3-(3-methylphenyl-2-oxoethyl)isobenzofuran-1(3H)-one (18) (IC50 values obtained for HL-60, K562 and NALM6 were, respectively, 13.5 μmol L-1, 8.83 μmol L-1, and 5.24 μmol L-1). In addition, compound 18 was capable of triggering apoptosis on NALM6 cells. All isobenzofuranones herein evaluated did not present cytotoxicity on peripheral blood mononuclear cells (PBMC), suggesting selective cytotoxic effect on leukemic cells. A computational study allowed prediction of pharmacokinetics and drug-likeness properties of the synthesized compounds. DFT calculations were performed to obtain the energy values of HOMO, LUMO, and dipole moments of isobenzofuranones.
Practical route to a new class of LTD4 receptor antagonists
Larsen, Robert D.,Corley, Edward G.,King, Anthony O.,Carroll, James D.,Davis, Paul,Verhoeven, Thomas R.,Reider, Paul J.,Labelle, Marc,Gauthier, Jacques Y.,Xiang, Yi Bin,Zamboni, Robert J.
, p. 3398 - 3405 (2007/10/03)
A general approach to the synthesis of a new class of LTD4 antagonists is presented. The key diarylpropane framework was prepared by Claisen-Schmidt condensation and selective reduction of the enone. Depending on the bridge to the 7-chloroquinaldine moiety, alkylation or Heck coupling methodology was developed. The chiral sulfides were introduced by asymmetric reduction of the diarylpropanone intermediates and subsequent inversion of the chiral center.
