21763-07-5

Usage

Uses

Used in Pharmaceutical Synthesis:
6,7-dimethoxy-1,4-dihydro-3(2H)-isoquinolinone (SALTDATA: FREE) is used as a key intermediate in the synthesis of various pharmaceuticals for its potential medicinal properties. Its unique structure allows it to be a versatile building block in the development of new drugs.
Used in Research and Development:
In the field of research and development, 6,7-dimethoxy-1,4-dihydro-3(2H)-isoquinolinone (SALTDATA: FREE) serves as a valuable compound for exploring its potential biological activities and medicinal applications. Scientists and researchers utilize 6,7-dimethoxy-1,4-dihydro-3(2H)-isoquinolinone(SALTDATA: FREE) to study its interactions with biological systems and to develop a better understanding of its therapeutic potential.
Used in Medicinal Property Studies:

InChI:InChI=1/C11H13NO3/c1-14-9-3-7-5-11(13)12-6-8(7)4-10(9)15-2/h3-4H,5-6H2,1-2H3,(H,12,13)

Upstream product

• 50-00-0 formaldehyd 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 16135-41-4 6,7-dimethoxy-3,4-dihydro-1H-2-benzopyran-3-one 
• 73053-80-2 ethyl 2-(bromomethyl)-4,5-dimethoxyphenylacetate 
• 78222-21-6 3,4-dimethoxy-N-hydroxymethylphenylacetamide 
• 78222-23-8 4,5-dimethoxy-2-aminomethylphenylacetic acid bisamide 
• 100-97-0 hexamethylenetetramine 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 
• 340255-41-6 4,5-dimethoxy-2-[(phenylacetamino)methyl]phenylacetic acid 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 65836-72-8 2-chloro-N-(3,4-dimethoxybenzyl)acetamide 

Downstream Products

• 75938-11-3 2-(3',4'-Dimethoxy-β-phenethyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-3-isoquinolone 
• 523-02-4 2,3,10,11-tetramethoxy-5,6,7,8,13,13a-hexahydroisoquinolino[3,2-a]isoquinoline 
• 78893-43-3 6,7-Dimethoxy-4-[1-phenethylamino-meth-(Z)-ylidene]-1,4-dihydro-2H-isoquinolin-3-one 
• 78893-39-7 4-[1-Dimethylamino-meth-(Z)-ylidene]-6,7-dimethoxy-1,4-dihydro-2H-isoquinolin-3-one 
• 78893-39-7 3-oxo-4-dimethylaminomethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Regioselectivity in isoquinoline alkaloid synthesis

Regioselectivity in isoquinoline alkaloid synthesis is analyzed here. Our experiments have shown that substituents on the aromatic ring of the starting amine are determinant in isoquinoline synthesis. The use of dicyclohexylcarbodiimide in activating carb

An enzyme-labile safety catch linker for synthesis on a soluble polymeric support

The development of new and broadly applicable linker groups which are stable under a variety of reaction conditions and allow release of the desired products from the solid support under very mild conditions is of great interest in organic synthesis and combinatorial chemistry. We describe an enzyme-labile safety-catch linker which releases alcohols and amines through i) enzymatic cleavage of an amino group and ii)subsequent lactam formation. The linker group was investigated on different polymeric supports: TentaGel, PEGA, CPG-beads and the soluble polymer POE-6000. From these linker-polymer conjugates 2-methoxy-5-nitrobenzyl alcohol was released by penicillin G acylase catalysed cleavage of a phenylacetamide and attack of the liberated benzylamine on the neighbouring ester group in ortho position. The model study revealed that only in the case of soluble POE-6000 conjugate high yields for the cleavage could be achieved. In the case of the other solid supports the enzyme does not have access to the interior of the polymer matrix. The application of the POE-6000 linker conjugate was investigated for various esters in Pd0-catalysed Heck-Suzuki- and Sonogashira reactions as well as in a Mitsunobu reaction and cycloadditions. These studies proved that the linker is stable under a broad variety of reaction conditions and that the enzymatic method allows for release of the desired product alcohols under extremely mild conditions at pH 7 and 37°C. In addition, the enzymatic reaction proceeds with complete chemoselectivity, that is other esters or amides are not attacked by the biocatalyst. In addition to alcohols amines can also be cleaved by means of the enzyme-initiated two-step process. In these cases the higher stability of amides as compared to esters requires warming to 60°C to induce cyclization and release of the desired product.

Application of hexamethylenetetramine in a Pictet-Spengler type reaction for synthesis of isoquinoline derivatives

Hexamethylenetetramine was used successfully as amino- and amidoalkylation cyclization reagent for the synthesis of 3,4-dihydroisoquinolines, tetrahydroisoquinolines and 1,4-dihydro-3(2H)-isoquinolinones. The reagent provides a simple and convenient pathway for the preparation of a range of these compounds.

STUDIES ON THE SYNTHESIS OF BENZOLACTAM RINGS. II SYNTHESIS OF 1,4-DIHYDRO-3(2H)-ISOQUINOLINONE DERIVATIVES

A new synthesis of 1,4-dihydro-3(2H)-isoquinolinones by the amidomethylation with acrylacetamide or acrylacetonitrile and paraformaldehyde in some acid-catalysts is described.

Active-Site-Directed Inhibition of &α-Chymotrypsin by Deaminatively Produced Carbonium Ions: An Example of Suicide or Enzyme-Activated-Substrate Inhibition

N-Nitroso amides derived from phenylalanine and alanine were utilized as inhibitors of α-chymotrypsin.During the enzyme-catalyzed hydrolysis of these substrates, carbonium ions capable of alkylating nucleophilic groups are released in the active site.Nitroso lactams were also tested as substrates since they produce carbonium ions while still tethered to the enzyme at the acyl-enzyme stage.Kinetic studies indicated that at substrate/α-chymotrypsin ratios of 40:1 the acyclic substrates caused the following percent inhibition of α-chymotrypsin activity (substrate, percent inhibition): D-1a, 100; L-1a, 9; D-1c, 100; L-1c, 9.Nitroso lactams 2 and 3, in substrate/enzyme ratios of 54:1 and 20:1, respectively, caused 91 and 97percent inhibition of α-chymotrypsin activity.At low (6:1) substrate/enzyme ratios, the inhibition of nitroso lactam 3 was partially reversible.The extents of inhibition were decreased by the competitive inhibitor N-acetyl-L-tryptophan, indicating that the inhibitor substrates were acting at the active site.Radioactive analogues of D- and L-1a and of 3(14C) provided evidence that the inhibition was irreversible, since ca. 1.0 mol of the benzyl group of D-1a and ca. 1.6 mol of the aryl moiety in the case of 3 remained bound to the inhibited enzyme after dialysis or Sephadex G-25 chromatography (no alkylation occurred with L-1a).The enzymatic hydrolyses of the L isomers of phenylalanine substrates (1a,b) were faster than those of the D enantiomers, whereas in the alanine series (1c) the rate ratio was reversed.A model based on "reverse" binding of the two aromatic groups of substrates D-1a and D-1c in the enzyme active site is proposed to explain the hydrolysis rate and the preferential inhibition of α-chymotrypsin by the D antipodes.

A NEW SYNTHESIS OF 1,4-DIHYDRO-3(2H)-ISOQUINOLINONES BY THE CYCLIZATION OF N-HYDROXYMETHYLARYLACETAMIDES

A new and facile synthesis of 1,4-dihydro-3(2H)-isoquinolinones by the intramolecular amidomethylation with pyrophosphoric acid is described.

Basically substituted 1,4-dihydro-2H-isoquinoline derivatives and process for preparing them

1,4-Dihydro-2H-isoquinoline derivatives of the general formula I SPC1 in which R1 represents hydrogen or straight chain or branched alkyl of 1 to 6 carbon atoms, R2 represents low molecular dialkylaminoalkyl, in which both alkyl groups of the dialkylamino group together with the nitrogen atom may also form a 5-, 6- or 7-membered saturated ring in which one carbon atom may be substituted by an oxygen atom, a sulfur atom or another nitrogen atom which may be substituted by hydrogen, C1 -C4 -alkyl or phenyl, or R1 and R2 together may form a 5- or 6-membered saturated ring containing 1 nitrogen atom, R3 represents phenyl which may be mono- or di-substituted by halogen, nitro, amino or sulfamoyl, or acylamino or alkyl each containing 1 to 4 carbon atoms, or pyridyl R4 and R5, which may identical or different, represent hydrogen or alkoxy of 1 to 4 carbon atoms, and X represent oxygen or sulfur, Their physiologically tolerated salts, process for preparing them. The compounds are active on the coronary circulation and are distinguished in particular by an anti-arrhythmic action and may, therefore, be used in the treatment of disorders of the heart rhythm.