109082-14-6

Basic information

• Product Name: 4-phenylindoline-2,3-dione
• Synonyms: 4-phenylindoline-2,3-dione
• CAS NO: 109082-14-6
• Molecular Weight: 223.231
• Mol File: 109082-14-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-phenylindoline-2,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenylindoline-2,3-dione(109082-14-6)
• EPA Substance Registry System: 4-phenylindoline-2,3-dione(109082-14-6)

Safety Data

• Hazardous Substances Data: 109082-14-6(Hazardous Substances Data)

Upstream product

• 20780-75-0 4-iodo-1H-indole-2,3-dione 
• 98-80-6 phenylboronic acid 
• 2243-47-2 3-biphenyl amine 
• 63608-68-4 3-iodo-isonitrosoacetanilide 
• 626-01-7 3-Iodoaniline 

Downstream Products

• 4432-98-8 6-phenylanthranilic acid 
• 1233940-40-3 N-methyl-4-phenylindoline-2,3-dione 

Relevant articles and documents

Efficient synthesis of bulky 4-substituted-isatins via microwave-promoted Suzuki cross-coupling reaction

Indoline-2,3-diones (isatins) and their derivatives are important heterocycles found in nature and present in numerous bioactive compounds. Very few examples related to the synthesis of 4-substituted-arylisatins have been reported before. Utilizing microwave irradiation, the synthesis of bulky 4-substituted-arylisatins via a Suzuki cross-coupling has been developed with a wide range of substrates. All the reactions proceeded smoothly and afforded moderate to excellent yields of products, which indicating that electronic effects and steric modifications have little effect on this reaction.

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Leukocyte recruitment of sites of inflammation and tissue injury involves leukocyte rolling along the endothelial wall, followed by firm adherence of the leukocyte, and finally transmigration of the leukocyte across cell junctions into the underlying tissue. The initial rolling step is mediated by the interaction of leukocyte glycoproteins containing active moieties such as sialyl Lewisx (sLex) with P-selectin expressed on endothelial cells. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of inflammatory diseases such as arthritis. High-throughput screening of the Wyeth chemical library identified the quinoline salicylic acid class of compounds (1) as antagonists of P-selectin, with potency in in vitro and cell-based assays far superior to that of sLex. Through iterative medicinal chemistry, we identified analogues with improved P-selectin activity, decreased inhibition of dihydrooratate dehydrogenase, and acceptable CYP profiles. Lead compound 36 was efficacious in the rat AIA model of rheumatoid arthritis.