6917-30-2

Basic information

• Product Name: 2-(2-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)- dione
• Synonyms: 2-(2-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)- dione
• CAS NO: 6917-30-2
• Molecular Weight: 289.29
• Mol File: 6917-30-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-(2-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)- dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)- dione(6917-30-2)
• EPA Substance Registry System: 2-(2-hydroxyphenyl)-1H-benzo[de]isoquinoline-1,3(2H)- dione(6917-30-2)

Safety Data

• Hazardous Substances Data: 6917-30-2(Hazardous Substances Data)

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 62-53-3 aniline 
• 6914-98-3 2-phenylbenzo[de]isoquinoline-1,3-dione 
• 95-55-6 2-amino-phenol 

Downstream Products

• 1335137-99-9 sodium salt of N-[2-(3-sulfopropoxy)phenyl]-1,8-naphthalimide 
• 1335138-05-0 potassium salt of N-[2-(3-sulfopropoxy)phenyl]-1,8-naphthalimide 
• 1335138-04-9 N-[2-(1,1-difluoro-2-ethoxy-2-oxoethoxy)phenyl]-1,8-naphthalimide 
• 1335138-02-7 2-(2-(prop2-yn-1-yloxy)phenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Relevant articles and documents

Synthesis of N-(2-hydroxyphenyl)-1,8-naphthalimide and its derivatization at the hydroxy group

The reaction of 1,8-naphthalic anhydride with 2-aminophenol afforded N-(2-hydroxyphenyl)-1,8-naphthalimide, which was then derivatized at the hydroxy group.

Modelling and Phenotypic Screening of NAP-6 and 10-Cl-BBQ, AhR Ligands Displaying Selective Breast Cancer Cytotoxicity in Vitro

To exploit the interaction of the aryl hydrocarbon receptor (AhR) pathway in developing breast-cancer-specific cytotoxic compounds, we examined the breast cancer selectivity and the docking pose of the AhR ligands (Z)-2-(2-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (NAP-6; 5) and 10-chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (10-Cl-BBQ; 6). While the breast cancer selectivity of 5 in vitro is known, we discuss the SAR around this lead and, by using phenotypic cell-line screening and the MTT assay, show for the first time that 6 also presents with breast cancer selectivity, notably in the triple-negative (TN) receptor breast cancer cell line MDA-MB-468, the ER+ breast cancer cell lines T47D, ZR-75-1 and the HER2+ breast cancer cell line SKBR3 (GI50 values of 0.098, 0.97, 0.13 and 0.21 μM, respectively). Indeed, 6 is 55 times more potent in MDA-MB-468 cells than normal MCF10A breast cells (GI50 of 0.098 vs 5.4 μM) and more than 130 times more potent than in cell lines derived from pancreas, brain and prostate (GI50 of 0.098 vs 10–13 μM). Molecular docking poses of 5 and 6 together with analogue synthesis and phenotypic screening show the importance of the naphthalene moiety, and an ortho-disposed substituent on the N-phenyl moiety for biological activity.

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.