13670-91-2

Basic information

• Product Name: 1(2H)-Isoquinolinone, 3-(4-methoxyphenyl)-
• CAS NO: 13670-91-2
• Molecular Formula: C16H13NO2
• Molecular Weight: 251.285
• Mol File: 13670-91-2.mol
• Article Data: 24

Chemical Properties

• CAS DataBase Reference: 1(2H)-Isoquinolinone, 3-(4-methoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1(2H)-Isoquinolinone, 3-(4-methoxyphenyl)-(13670-91-2)
• EPA Substance Registry System: 1(2H)-Isoquinolinone, 3-(4-methoxyphenyl)-(13670-91-2)

Safety Data

• Hazardous Substances Data: 13670-91-2(Hazardous Substances Data)

Upstream product

• 2170-09-4 N,2-dimethylbenzamide 
• 874-90-8 4-methoxybenzonitrile 
• 100-66-3 methoxybenzene 
• 25407-08-3 2-((4-methoxyphenyl)ethynyl)benzamide 
• 130818-20-1 2-(2-(4-methoxyphenyl)ethynyl)benzoic acid methyl ester 
• 768-60-5 4-methoxyphenylacetylen 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 5720-07-0 4-methoxyphenylboronic acid 
• 5597-04-6 2-cyanomethylbenzoic acid methyl ester 
• 2728-04-3 N,N-diethyl-ortho-toluamide 
• 4387-36-4 2-iodobenzonitrile 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 873-32-5 2-Chlorobenzonitrile 
• 2042-37-7 o-cyanobromobenzene 

Downstream Products

• 20434-92-8 3-(4-hydroxyphenyl)-2H-isoquinolin-1-one 
• 20435-80-7 1,4-dichloro-3-(4-methoxy-phenyl)-isoquinoline 
• 181371-92-6 [3-(4-Methoxy-phenyl)-1-oxo-1,2-dihydro-isoquinolin-4-yl]-carbamic acid ethyl ester 
• 181372-16-7 N-[3-(4-Methoxy-phenyl)-1-oxo-1,2-dihydro-isoquinolin-4-yl]-acetamide 
• 181371-88-0 ICC₁08-L-006-G₀₈- 

Relevant articles and documents

Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones

A striking dependence on the method of workup has been found for annulation of benzonitriles ArCN to N-methyl 2-toluamide (1), facilitated by n-BuLi (2 equiv): Quenching the reaction by a slow addition of water produced the expected 1-isoquinolones 2; by

Triflic acid mediated sequential cyclization of ortho-alkynylarylesters with ammonium acetate

A triflic acid (TfOH) mediated sequential cyclization of ortho-alkynylarylesters and ammonium acetate (NH4OAc) was reported. The reaction took place via a Br?nsted acid-mediated intramolecular cyclization of ortho-alkynylarylesters followed by an ammonium acetate participated substitution reaction, forming isoquinolin-1-ones as the major products. Different from most of the known synthetic methods of isoquinolin-1-ones, no metal catalyst was required in the reported reaction. The regioisomers – isoindolin-1-ones were obtained together with isoquinolin-1-ones in a few cases. The intermediate compounds – isochromen-1-ones and isobenzofuran-1-ones were also isolated. The interconversion experiments showed that the regioisomers formed during the Br?nsted acid induced intramolecular cyclization of ortho-alkynylarylesters. A natural product – ruprechstyril was prepared in a moderate yield employing the new method.

Design, synthesis, and biological evaluation of 1,3-diarylisoquinolines as novel topoisomerase I catalytic inhibitors

With a goal of identifying potent topoisomerase (topo) inhibitor, the C4-aromatic ring of the anticancer agent, 3,4-diarylisoquinolone, was strategically shifted to design 1,3-diarylisoquinoline. Twenty-two target compounds were synthesized in three simple and efficient steps. The 1,3-diarylisoquinolines exhibited potent anti-proliferative effects on cancer cells but few compounds spared non-cancerous cells. Inhibition of topo I/IIα-mediated DNA relaxation by several derivatives was greater than that by camptothecin (CPT)/etoposide even at low concentration (20 μM). In addition, these compounds had little or no effect on polymerization of tubulin. A series of biological evaluations performed with the most potent derivative 4cc revealed that the compound is a non-intercalative topo I catalytic inhibitor interacting with free topo I. Collectively, the potent cytotoxic effect on cancer cells including the drug resistance ones, absence of lethal effect on normal cells, and different mechanism of action than topo I poisons suggest that the 1,3-diarylisoquinolines might be a promising class of anticancer agents worthy of further pursuit.