3973-56-6

Usage

General Description

The chemical 1(3H)-Isobenzofuranone, 3-[(2-chlorophenyl)methylene]-, also known as 2-chlorophenyl-methylene-dihydrofuran-3(H)-one, is a compound with a molecular formula of C14H9ClO2. It is a derivative of isobenzofuranone and contains a chlorophenyl group attached to the carbon atom in the 3-position of the isobenzofuranone ring. 1(3H)-Isobenzofuranone, 3-[(2-chlorophenyl)methylene]- is commonly used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its specific properties and applications may vary depending on the exact chemical structure and functional groups attached to the molecule.

Upstream product

• 2444-36-2 2'-chloro-benzeneacetic acid 
• 85-44-9 phthalic anhydride 
• 873961-52-5 2-((2-chlorophenyl)ethynyl)benzaldehyde 
• 873-31-4 2-chlorophenylacetylene 
• 88-65-3 2-bromobenzoic-acid 
• 36136-61-5 2-chloro-2'-hydroxychalcone 
• 1183501-63-4 C₁₄H₁₀BrClO 
• 1864-94-4 phenyl formate 

Downstream Products

• 3973-46-4 2-<2-(2-Chlor-phenyl)-aethyl>-benzoesaeure 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents

We designed a series of substituted flavones and aurones as non-competitive H1N1 neuraminidase (NA) inhibitors and anti-influenza agents. The molecular docking studies showed that the designed flavones and aurones occupied 150-cavity and 430-cavity of H1N1-NA. We then synthesized these compounds and evaluated these for cytotoxicity, reduction in H1N1 virus yield, H1N1-NA inhibition and kinetics of inhibition. The virus yield reduction assay and H1N1-NA inhibition assay demonstrated that the compound 1f (4-methoxyflavone) had the lowest EC50 of 9.36 nM and IC50 of 8.74 μM respectively. Moreover, kinetic studies illustrated that compounds 1f and 2f had non-competitive inhibition mechanism.

Palladium-catalyzed carbonylative synthesis of isocoumarins and phthalides by using phenyl formate as a carbon monoxide source

A simple and efficient palladium-catalyzed intramolecular carbonylative synthesis of isocoumarins and phthalides from the easily available starting materials by employing phenyl formate as a CO surrogate has been achieved. The approach affords target compounds in good to excellent yields with the advantages of lower toxicity, milder conditions, easy operation and wide functional group tolerance.

Pd-free Sonogashira coupling: One pot synthesis of phthalide via domino Sonogashira coupling and 5-exo-dig cyclization

Phthalides have been synthesized exclusively in one pot via Pd-free Sonogashira coupling. A Cu-catalyzed domino Sonogashira coupling and 5-exo-dig cyclization between suitable substituted ortho-bromobenzoic acids and terminal alkynes afforded phthalides in good yields under mild reaction conditions.

New method for the synthesis of lactones via nickel-catalyzed isocyanides insertion

A novel nickel catalyst for the reaction of tert-butyl isocyanide insertion was discovered. In this approach, 1,2-bis(diphenylphosphino)ethane (L3) serves as an efficient ligand, thereby allowing the preparation of lactones from (o-bromophenyl)phenylethanone derivatives. It is noteworthy that this is the first example of nickel acting as a metal catalyst in the reactions of tert-butyl isocyanide insertion. The significance of this methodology may draw many chemists attention in the field of isocyanide-incorporating reactions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Palladium-catalyzed synthesis of isocoumarins and phthalides via tert -butyl isocyanide insertion

A novel and highly efficient strategy for the synthesis of isocoumarins and phthalides through a palladium(0)-catalyzed reaction incorporating tert-butyl isocyanide has been developed. This process, providing one of the simplest methods for the synthesis of this class of valuable lactones, involves two steps including cyclization reaction and simple acid hydrolysis. The methodology is tolerant of a wide range of substrates and applicable to library synthesis.

Antimalarial activity of imidazo[2,1-a]isoindol-5-ol derivatives and related compounds

The synthesis of several series of imidazo[2,1-a]isoindol-5-ol derivatives and the results of their evaluation against Plasmodium falciparum are presented and discussed. The effects of electron-withdrawing or-donating substituents on different parts of the molecule, as well as those produced by the incorporation of an additional fused ring, were analyzed. Several compounds showed significant antimalarial activity in vitro with IC50 values as low as 60 nM and a certain efficacy in vivo by reducing parasitemia in Plasmodium berghei mouse models.

One-pot synthesis of phthalides via regioselective intramolecular cyclization from ortho-alkynylbenzaldehydes

A one-pot synthesis of phthalides via an intramolecular 5-exo-dig cyclization of ortho-alkynylbenzaldehydes under mild NaClO2 oxidation conditions is described.

Anti-HIV activity of stilbene-related heterocyclic compounds

Viral transcription has not been routinely targeted in the development of new antiviral drugs. This crucial step of the viral cycle depends on the concerted action of cellular and viral proteins such as NF-κB and Tat. In the present study, stilbene-related heterocyclic compounds including benzalphthalide, phthalazinone, imidazoindole and pyrimidoisoindole derivatives are tested for their anti-HIV activity. Original assays based on recombinant viruses were used to evaluate HIV replication inhibition and stably transfected cell lines were used to evaluate inhibition of Tat and NF-κB proteins. Some of the stilbene-related heterocyclic compounds analysed displayed anti-HIV activity through interference with NF-κB and Tat function. Moreover, compounds inhibiting both targets displayed a stronger activity on viral replication.

Vasorelaxant activity of phthalazinones and related compounds

Several series of dihydrostilbenamide, imidazo[2,1-a]isoindole, pyrimido[2,1-a]isoindole and phthalazinone derivatives were obtained and their vasorelaxant activity was measured on isolated rat aorta rings pre-contracted with phenylephrine (10-5 M). Some phthalazinones attained, practically, the total relaxation of the organ at micromolar concentrations. For the most potent compound 9h (EC50 = 0.43 μM) the affinities for α1A, α1B and α1D adrenergic sub-receptors were determined.