83907-64-6

Basic information

• Product Name: 2-(4-chlorophenyl)isoquinoline-1,3(2H,4H)-dione
• Synonyms: 1,3(2H,4H)-Isoquinolinedione, 2-(4-chlorophenyl)-
• CAS NO: 83907-64-6
• Molecular Formula: C₁₅H₁₀ClNO₂
• Molecular Weight: 271.6984
• Mol File: 83907-64-6.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 475.5°C at 760 mmHg
• Flash Point: 241.4°C
• Density: 1.383g/cm³
• Vapor Pressure: 3.31E-09mmHg at 25°C
• Refractive Index: 1.649
• CAS DataBase Reference: 2-(4-chlorophenyl)isoquinoline-1,3(2H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chlorophenyl)isoquinoline-1,3(2H,4H)-dione(83907-64-6)
• EPA Substance Registry System: 2-(4-chlorophenyl)isoquinoline-1,3(2H,4H)-dione(83907-64-6)

Safety Data

• Hazardous Substances Data: 83907-64-6(Hazardous Substances Data)

Usage

Chemical class

Isoquinoline

Physical appearance

Yellow, crystalline solid

Primary use

Organic synthesis and pharmaceutical research

Potential applications

Medicinal properties, treatment of various diseases and conditions

Additional use

Building block in the synthesis of more complex organic compounds

Upstream product

• 89-51-0 Homophthalic acid 
• 106-47-8 4-chloro-aniline 
• 703-59-3 homophthalic anhydride 

Downstream Products

• 708976-46-9 C₁₇H₁₄ClNO₂ 
• 1060750-39-1 C₂₁H₂₂ClNO₂ 
• 1060750-38-0 C₁₉H₁₈ClNO₂ 
• 1060750-42-6 C₂₀H₁₈ClNO₂ 
• 1060750-41-5 C₁₉H₁₆ClNO₂ 
• 113293-27-9 3-chloro-2-(4-chlorophenyl)isoquinolin-1(2 H)-one 
• 183489-18-1 4-Benzoyloxy-2-(4-chloro-phenyl)-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid ethyl ester 
• 183489-02-3 2-(4-Chloro-phenyl)-1,3-dioxo-1,2,3,4-tetrahydro-isoquinoline-4-carboxylic acid ethyl ester 

Relevant articles and documents

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.

Microwave promoted one-pot synthesis of some novel N-aryl isoquinoline derivatives

Homophthalic anhydride 1 reacts with different aromatic amines to produce N-substituted homophthalimides 2 under microwave irradiation. A rapid microwave-assisted chemical synthesis of condensed 4-substituted furo[2,3-c]isoquinoline-1,5(2H,4H)-diones 3 an

Progesterone receptor antagonists with a 3-phenylquinazoline-2,4-dione/2-phenylisoquinoline-1,3-dione skeleton

Novel non-steroidal progesterone receptor antagonists with a 3-phenylquinazoline-2,4-dione/2-phenylisoquinoline-1,3-dione skeleton were developed and their structure-activity relationships were investigated. Among the prepared compounds, 4-(4,4-diethyl-3,