25287-05-2

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General Description

2-(4-amino-phenyl)-benzo[de]isoquinoline-1,3-dione, also known as BIDQ, is a chemical compound that belongs to the benzo[de]isoquinoline class. It consists of a benzene ring fused to a decahydroisoquinoline and a cyclic dione ring. BIDQ is known for its potential biological activities, including anti-inflammatory, anti-cancer, and anti-microbial properties. It has also been studied for its potential in treating neurological disorders, such as Alzheimer's disease. BIDQ is a versatile compound with potential applications in the pharmaceutical and medical industries.

InChI:InChI=1/C18H12N2O2/c19-12-7-9-13(10-8-12)20-17(21)14-5-1-3-11-4-2-6-15(16(11)14)18(20)22/h1-10H,19H2

Upstream product

• 81-84-5 1,8-Naphthalic anhydride 
• 106-50-3 1,4-phenylenediamine 
• 100-01-6 4-nitro-aniline 

Relevant academic research and scientific papers

Toward intrinsically fluorescent proteomimetics: Fluorescent probe response to alpha helix structure of poly-γ-benzyl-l-glutamate

A fluorescent probe (1), developed for recognition of alpha helical secondary structure, shows a large fluorescence change upon titration with the synthetic protein PBLG. Compared to fluorophores of similar size and shape, 1 displayed the smallest dissoci

A tripodal supramolecular sensor to successively detect picric acid and CN? through guest competitive controlled AIE

Efficient detection of explosives (e.g. picric acid) and toxic compounds (e.g. cyanide) is an important task. Herein, we report a simple and efficient method for the selective and sensitive detection of picric acid (PA) and CN?via a novel guest

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.

Cyanide ion sensor molecule as well as synthesis and application thereof

The invention discloses a cyanide ion sensor molecule which is a novel sensor molecule HB1, is prepared by condensing a 4-aminophenyl functionalized 1,8-naphthalimide derivative with 4-lignocaine salicylaldehyde in a synthesis manner, and is of a naphthal

Sensor molecules based on naphthalimide derivatives and their synthesis and application

The invention discloses sensor molecules TN based on naphthalimide derivatives. The sensor molecules are C63H36N6O9 and employ naphthalimides as fluorescence signal reporter groups and three amide groups as hydrogen bond sites such that the molecules have

An Efficient Microwave-Assisted Synthesis of Novel 2-{4-[(3-Aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones and Their Antimicrobial Activity

The Buchwald–Hartwig amination reaction between 2-chloro-3-aryl-1,8-naphthyridines and 2-(4-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione in the presence of the catalytic system Pd(PPh3)4 and the base KO-t-Bu in toluene was studied. The reaction was initiated by microwave irradiation. Highly efficient synthesis has been developed for 2-{4-[(3-aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones. Structures of the synthesized compounds were evaluated by IR, 1H and 13C NMR spectroscopy. All products were tested for antimicrobial activity against Escheria coli, Bacillus subtilis, Klebsiella pneumoniae, and Staphylococcus aureus.

Iron ion sensor molecule with hydroxy naphthaldehyde structure and synthesis and application thereof

The invention discloses an iron ion sensor molecule with a hydroxy naphthaldehyde structure. The iron ion sensor molecule is obtained by using 1,8-naphthalic anhydride and phenylenediamine as starting raw materials to synthesize an intermediate and then m

Ionic liquids accelerate access to N-substituted-1,8-naphthalimides

The synthesis of N-substituted-1,8-naphthalimides is accelerated in the presence of the room temperature ionic liquid [BMIM][NO3]. Reaction times are reduced from 18 h in volatile organic compounds (VOCs) (PhCH 3, EtOH and THF) to 20 min in the ionic liquid [BMIM][NO 3]. The reaction yields are typically increased to >85% and the products are isolated by ethanol-mediated precipitation direct from the ionic liquid, requiring no further purification. Crown Copyright