84989-99-1

Usage

Uses

Used in Pharmaceutical Industry:
(4Z)-7,9-dichloro-8-hydroxy-4-[(4-methoxyphenyl)amino]methylidenedibenzo[b,d]furan-3(4H)-one is used as a potential therapeutic agent for [application reason], such as targeting specific biological pathways or receptors due to its unique molecular structure and properties.
Used in Agrochemical Industry:
In the agrochemical sector, (4Z)-7,9-dichloro-8-hydroxy-4-[(4-methoxyphenyl)amino]methylidenedibenzo[b,d]furan-3(4H)-one is used as a possible active ingredient in the development of new pesticides or herbicides, leveraging its chemical properties to control or eliminate pests and unwanted plant species.
Used in Materials Science:
(4Z)-7,9-dichloro-8-hydroxy-4-[(4-methoxyphenyl)amino]methylidenedibenzo[b,d]furan-3(4H)-one is utilized as a component in the synthesis of novel materials with specific properties, such as improved stability, reactivity, or selectivity, for applications in various fields like electronics, coatings, or advanced materials.

Upstream product

• 26623-06-3 N-(4-methoxyphenyl)-2-(aminomethylene)cyclohexanone 
• 345941-43-7 7,9-dichloro-1,2-dihydro-8-hydroxy-4-[(4-methoxyphenylamino)methylene]dibenzo[b,d]furan-3(2H)-one 
• 84989-98-0 7,9-Dichlor-1,4,4a,9b-tetrahydro-8-hydroxy-4-<(4-methoxyphenylamino)methylen>dibenzofuran-3(2H)-on 
• 697-91-6 2,6-dichloro-1,4-benzoquinone 

Relevant academic research and scientific papers

A π‐halogen bond of dibenzofuranones with the gatekeeper phe113 in human protein kinase CK2 leads to potent tight binding inhibitors

Human protein kinase CK2 is an emerging target for neoplastic diseases. Potent lead structures for human CK2 inhibitors are derived from dibenzofuranones. Two new derivatives, 7,9‐dichloro‐1,2‐dihydro‐8‐hydroxy‐4‐[(4‐methoxyphenylamino)‐methylene]dibenzo[b,d]furan‐3(2 H)‐one (4a) and (E)‐1,3‐dichloro‐6‐[(4‐methoxyphenylimino)‐methyl]dibenzo[b,d]furan‐2,7‐diol (5) were tested for inhibition of CK2 and induction of apoptosis in LNCaP cells. Both turned out to be tight binding inhibitors, with IC50 values of 7 nM (4a) and 5 nM (5) and an apparent Ki value of 0.4 nM for both. Compounds 4a and 5 reduced cellular CK2 activity, indicating cell permeability. Cell viability was substantially impaired in LNCaP cells, as well as apoptosis was induced, which was not appearing in non‐neoplastic ARPE‐19 cells. Co‐crystallization of 4a and 5 revealed an unexpected π‐halogen bond of the chloro substituent at C9 with the gatekeeper amino acid Phe113, leading to an inverted binding mode in comparison to parent compound 4b, with the Cl at C6 instead, which was co‐crystallized as a control. This indicates that the position of the chloro substituent on ring A of the dibenzofuran scaffold is responsible for an inversion of the binding mode that enhances potency.

Reaction of 2-(Aminomethylene)cyclohexanone Derivatives with Dichloroquinones

Reaction of dichloro-p-benzoquinones 1 with 2-cyclohexanone derivatives 2 yield dibenzofuranone derivatives 4.The structure is proven spectroscopically and by oxidation to 6, which is hydrolysed to 7.The course of the reaction via the intermediate 10 can be proved by its isolation and reaction to 4a.