55222-45-2Relevant articles and documents
Microwave-assisted solid acid-catalyzed one-pot synthesis of isobenzofuran-1(3H)-ones
Landge, Shainaz M.,Berryman, Martin,T?r?k, Béla
, p. 4505 - 4508 (2008)
A new, solid acid-catalyzed microwave-assisted environmentally benign synthesis of isobenzofuran-1(3H)-ones is described. Montmorillonite K-10 appeared to be an excellent catalyst for the condensation and successive lactonization reactions. Reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl and cyclic ketones was initiated by microwave irradiation and occurred in one step. The reactions were complete in 10-30 minutes providing excellent yields (90-98%).
Practical synthesis of 3-(2-arylethylidene)isoindolin-1-ones (analogues of AKS-182) and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones
Ordó?ez, Mario,Palillero-Cisneros, Angel,Labastida-Galván, Victoria,Terán-Vázquez, Joel Luis
, (2019/12/24)
A simple and practical method is reported for the synthesis of 3-(2-arylethylidene)isoindolin-1-ones and 3-(2-arylethylidene)isobenzofuran-1(3H)-ones, proceeding with good to excellent yields and (E:Z) selectivity. This methodology involves the sequential reduction-dehydration reaction of readily obtained 3-(2-oxo-2-arylethyl)isoindolin-1-ones and 3-(2-oxo-2-arylethyl)isobenzofuran-1(3H)-ones followed by a base-catalyzed double bond isomerization with K2CO3 in acetonitrile. The development of a concise synthesis of AKS-182 has been achieved using this methodology.
Efficient PhB(OH)2-catalyzed one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones under solvent free conditions
Palillero-Cisneros, Angel,Bedolla-Medrano, Mercedes,Ordó?ez, Mario
, p. 4174 - 4181 (2018/06/25)
An efficient and practical one-pot synthesis of 3-substituted isoindolin-1-ones and isobenzofuran-1(3H)-ones has been developed under solvent free-conditions using non-toxic and cheap phenylboronic acid as excellent catalyst. This strategy involves the sequential two-step Mannich/lactamization cascade reaction of inexpensive 2-formylbenzoic acid with primary amines and a wide variety of ketones, and an aldol/lactonization cascade reaction of 2-formylbenzoic acid with a broad range of ketones.
Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones
Sahoo, Subas Chandra,Nath, Utpal,Pan, Subhas Chandra
supporting information, p. 4434 - 4438 (2017/08/23)
Valuable and direct aerobic oxidation reactions of 2-hydroxyacetophenones were explored. The concept was based on the in situ treatment of small quantities of aerobically formed α-keto aldehydes that drove the reactions to the corresponding products. This new strategy was applied for a variety of oxidative reactions of 2-hydroxyacetophenones, and valuable products such as phthalides, quinoxalines, and α-keto amides were obtained in good to high yields.
Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol
Jia, Lina,Han, Fuzhong
supporting information, p. 1425 - 1429 (2017/07/28)
Background: Phthalides are privileged constituents of numerous pharmaceuticals, natural products and agrochemicals and exhibit several biological and therapeutic activities. Therefore, the development of new, facile, and sustainable strategies for the construction of these moieties is highly desired. Results: A broad substrate scope for β-keto acids was found to be strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Conclusion: A concise and efficient synthesis strategy of 3-substituted phthalides from 2-formylbenzoic acid and β-keto acids via a catalytic one-pot cascade reaction in glycerol has been accomplished.
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.
One-pot synthesis of isobenzofuran-1(3H)-ones using sulfuric acid immobilized on silica under solvent-free conditions and survey of third-order nonlinear optical properties
Maleki, Behrooz,Koushki, Ehsan,Baghayeri, Mehdi,Ashrafi, Samaneh Sedigh
, p. 2827 - 2831 (2015/06/02)
Solvent-free synthesis of isobenzofuran-1(3H)-ones have been described via reaction of phthalaldehydic acid (2-carboxybenzaldehyde) with methylaryl or cyclic ketones using sulfuric acid immobilized on silica (H2SO4-SiO2) in excellent yields (70-88%). The catalyst can be recovered by simple filtration and reused. Also, some of these compounds has been studied the third-order nonlinear optical properties by laser Gaussian z-scan techniques.
1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles: An efficient and reusable catalyst for synthesis of mono- and bis-isobenzofuran-1(3H)-ones under solvent-free conditions
Rastegari, Forouz,Mohammadpoor-Baltork, Iraj,Khosropour, Ahmad R.,Tangestaninejad, Shahram,Mirkhani, Valiollah,Moghadam, Majid
, p. 15274 - 15282 (2015/02/19)
1-Methyl-3-(propyl-3-sulfonic acid)imidazolium triflate supported on magnetic nanoparticles ([HSO3PMIM]OTf-SiO2@MNPs) was prepared by immobilization of [HSO3PMIM]OTf onto the surface of silica-coated Fe3O4 nanoparticles and characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), and FT-IR techniques. Efficient synthesis of mono- and bis-isobenzofuran-1(3H)-ones was performed in the presence of this catalyst under thermal conditions and MW irradiation. The catalyst could be easily separated by an external magnet and reused six times under thermal conditions and MW irradiation without significant loss of its activity.
One pot solvent free synthesis and in vitro antitubercular screening of 3-Aracylphthalides against Mycobacterium tuberculosis
Limaye, Rohan A.,Kumbhar, Virendra B.,Natu, Arun D.,Paradkar, Madhusudan V.,Honmore, Varsha S.,Chauhan, Rubia R.,Gample, Suwarna P.,Sarkar, Dhiman
, p. 711 - 714 (2013/02/23)
One pot synthesis of 3-Aracylphthalide was accomplished in good yield by reacting 2-carboxy benzaldehyde with various aromatic methyl ketones in presence of methane sulphonic acid. Various phthalides thus obtained were characterized with spectral techniques. These phthalides were subjected to in vitro antitubercular screening against Mycobacterium tuberculosis H37Ra (MTB) by using XRMA protocol. Among the phthalides screened, four exhibited half maximal inhibitory concentration (IC50) in the range of 0.81-1.24 μg/ml thereby providing potential lead compounds for future drug discovery studies.
Benzofuranones as potential antinociceptive agents: Structure-activity relationships
Gon?alves, Cleiton José,Lenoir, Andrey Sávio,Padaratz, Pamela,Corrêa, Rogério,Niero, Rivaldo,Cechinel-Filho, Valdir,Campos Buzzi, Fátima De
, p. 120 - 126 (2013/01/15)
This work evaluates the antinociceptive properties of benzofuranones using chemically induced models of pain and the hot plate test. All the compounds exhibited significant antinociceptive activity, with 3-[2-(4-chlorophenyl)-2- oxoetil]-2-benzofuran-1(3H)-one (3d) being the most active. According to the application of the Topliss method, the 2π-π2 parameter was the preponderant one, indicating that the hydrophobicity (π) seems to be more involved in the antinociceptive activity. Based on the table of other possible substituents proposed by Topliss, three derived from compound 3d were tested. 3-[2-(3-methoxyphenyl)-2-oxoetil]-2-benzofuran-1(3H)-one (3g) showed greater antinociceptive activity with better pharmacokinetic properties predicted. These results show the efficiency of the Topliss Method as a research tool for the discovery of potential candidate molecules for a new antinociceptive drug.
