73270-77-6

Upstream product

• 119-67-5 o-carboxybenzaldehyde 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 87428-52-2 2-hydroxy-3'-methoxyacetophenone 
• 703-59-3 homophthalic anhydride 
• 1442748-91-5 C₁₁H₁₆O₄ 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 

Downstream Products

• 1422973-57-6 6-(3-methoxyphenyl)-7,7a-dihydro-12H-benzo[2,3][1,4]diazepino[7,1-a]isoindol-12-one 

Relevant academic research and scientific papers

Synthesis and spectral characterization of benzo-[6,7][1,5]diazocino[2,1-a]isoindol-12-(14h)-one derivatives

A simple synthetic route affording 27%-85% yields of benzo[6,7][1,5]diazocino[2,1-a]isoindol-12(14H)-one ring systems from readily available 3-(2-oxo-2-phenylethyl) isobenzofuran-1(3H)-ones and 2-(aminomethyl)aniline starting materials in toluene and catalysed by p-toluenesulfonic acid is developed. The 1H- and 13C-NMR spectra of the final products were assigned using a variety of one and two-dimensional NMR experiments. The distinction between the two potential isomers of the final products was made on the basis of heteronuclear multiple bond connectivity (HMBC) NMR spectra.

Synthesis of 1-(3H)isobenzofuranone compounds by tin powder promoted cascade condensation reaction

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.

Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones

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

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

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.

An approach to dihydroisoindolobenzodiazepinones - Three-dimensional molecular frameworks

A concise two-step procedure is developed for the preparation of dihydroisoindolobenzodiazepinones, which represent derivatives of three-dimensional molecular frameworks derived from classical privileged structures of medicinal chemistry. The method commences from the readily available starting materials (i.e., 2-formylbenzoic acid, o-phenylenediamine, and various ketones) and enables the synthesis of the title compounds in 58-82% overall yields.

Benzofuranones as potential antinociceptive agents: Structure-activity relationships

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.