16535-98-1

Basic information

• Product Name: bemarinone
• Synonyms: 6,7-DIMETHOXY-3-HYDROXY-1-METHYLISOQUINOLINE;6,7-dimethoxy-1-methylisoquinolin-3-ol;3(2H)-Isoquinolinone, 6,7-dimethoxy-1-methyl-;Orf 16600;6,7-dimethoxy-1-methyl-3(2H)-Isoquinolinone
• CAS NO: 16535-98-1
• Molecular Formula: C₁₂H₁₃NO₃
• Molecular Weight: 219.24
• Mol File: 16535-98-1.mol

Chemical Properties

• Boiling Point: 547.9°C at 760 mmHg
• Flash Point: 285.2°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 4.65E-12mmHg at 25°C
• Refractive Index: 1.575
• CAS DataBase Reference: bemarinone(CAS DataBase Reference)
• NIST Chemistry Reference: bemarinone(16535-98-1)
• EPA Substance Registry System: bemarinone(16535-98-1)

Safety Data

• Hazardous Substances Data: 16535-98-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13NO3/c1-7-9-6-11(16-3)10(15-2)4-8(9)5-12(14)13-7/h4-6H,1-3H3,(H,13,14)

Upstream product

• 17173-27-2 methyl 2-(2-acetyl-4,5-dimethoxyphenyl)acetate 
• 71655-15-7 CCH 18060 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 90149-75-0 ethyl 2-acetyl-4,5-dimethoxyphenylacetate 
• 77287-34-4 formamide 
• 59077-27-9 N-[2-(2-Acetyl-4,5-dimethoxy-phenyl)-acetyl]-acetamide 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 64-19-7 acetic acid 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 
• 18066-68-7 ethyl 3,4-dimethoxyphenylacetate 
• 108-24-7 acetic anhydride 
• 15964-79-1 methyl (3,4-dimethoxyphenyl)acetate 

Downstream Products

• 113983-23-6 4-(N'-Cyclohexylureido)-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113983-35-0 4-(N'-Phenylureido)-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113982-87-9 4-(N' para-methoxyphenylureido)-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 114052-45-8 4-[N'-(3-Methoxyphenyl)ureido]-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113983-42-9 4-(N'-para-carboxyphenylureido)-3-hydroxy-6,7-dimethoxy-methylisoquinoline 
• 113983-11-2 4-[N'-(4-Nitrophenyl)ureido]-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113983-00-9 4-[N'-(4-Trifluoromethylphenyl)ureido]-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113983-02-1 4-[N'-(3-Trifluoromethylphenyl)ureido]-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 113983-21-4 4-[N'-(4-Ethoxycarbonylphenyl)ureido]-3-hydroxy-6,7-dimethoxy-1-methylisoquinoline 
• 1393577-81-5 4-benzyl-6,7-dimethoxy-1-methylisoquinolin-3-ol hydrochloride 
• 1393577-85-9 6,7-dimethoxy-1-methyl-4-(4-phenoxybenzyl)isoquinolin-3-ol hydrochloride 
• 1415259-79-8 3-([1,1'-biphenyl]-3-yl)-1-(azidomethyl)-6,7-dimethoxyisoquinoline 
• 1415259-66-3 C₂₄H₂₂N₂O₂ 
• 1352035-53-0 2-((3-([1,1'-biphenyl]-3-yl)-6,7-dimethoxyisoquinolin-1-yl)methyl)guanidine 

Relevant articles and documents

INHIBITORS OF LYSINE METHYL TRANSFERASE

There are disclosed compounds that are inhibitors of EZH2, pharmaceutical compositions containing said compounds and methods of treating hyperproliferative, inflammatory, infectious, and immunoregulatory disorders and diseases, utilizing the compounds of

SUBSTITUTED 6,7-DIALKOXY-3-ISOQUINOLINOL DERIVATIVES AS INHIBITORS OF PHOSPHODIESTERASE 10 (PDE10A)

The invention relates to compounds of the formula wherein R′, R1, through R7 and Ar are as defined herein. These compounds are useful as inhibitors of phosphodiesterase 10 (PDE10A) which are useful in treating central nervous system diseases such as psychosis and also in treating, for example, obesity, type II diabetes, metabolic syndrome, glucose intolerance, pain and ophthalmic diseases.

Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding

The synthesis of a series of berberine, phenantridine and isoquinoline derivatives was realized to explore their Rho GTPase nucleotide inhibitory activity. The compounds were evaluated in a nucleotide binding competition assay against Rac1, Rac1b, Cdc42 and in a cellular Rac GTPase activation assay. The insertion of 19 AA in the splice variant Rac1b is shown to be sufficient to introduce a conformational difference that allows compounds 4, 21, 22, and 26 to exhibit selective inhibition of Rac 1b over Rac1.

Expedient synthesis of 3-hydroxyisoquinolines and 2-hydroxy-1,4- naphthoquinones via one-pot aryne acyl-alkylation/condensation

A convenient method is disclosed for the synthesis of both 3-hydroxyisoquinolines and 2-hydroxy-1,4-naphthoquinones from β-ketoesters using a one-pot aryne acyl-alkylation/condensation procedure. When performed in conjunction with a one-step method for the synthesis of the β-ketoester substrates, this method provides a new route to these polyaromatic structures in only two steps from commercially available carboxylic acid starting materials. The utility of this approach is demonstrated in the synthesis of the atropisomeric P,N-ligand, QUINAP. The Royal Society of Chemistry 2009.

Synthesis of isoquinolines from 2-phenylethylamines, amides, nitriles and carboxylic acids in polyphosphoric acid

A convenient one pot synthesis of 1-, 1.3-substituted 3,4-dihydroisoquinolines 5 enamines 10 and 3-oxo-2,3-dihydroisoquinolines 18 as well as of enamides 22 of isoquinoline from 2-phenyl-, 1,2-diphenylethylamines, phenylacetamides, phenylacetonitriles, N-acylphenylethylamines and carboxylic acids in nonaqueous media has been accomplished.

Synthesis of 3-oxo-2,3-dihydroisoquinolines from ethyl 2-acylphenylacetates and formamides

1- and 1,3-substituted 3-oxo-2,3-dihydroisoquinolines 4 are obtained from ethyl 2-acylphenylacetates 3 and formamides.

Isoquinolinol derivatives: potent, short-acting inotropic and vasodilating agents with potential utility for cardiac emergencies

The synthesis and cardiovascular evaluation of a series of 4-nitroisoquinolin-3-ol derivatives are reported.These compounds are potent, short-acting cardiovascular agents with both positive inotropic and peripheral vasodilating effects when administered i

Cardiotonic Agents. Synthesis and Inotropic Activity of a Series of Isoquinolin-3-ol Derivatives

A series of isoquinolin-3-ol derivatives (II) was prepared as analogues of the clinical cardiotonic agent bemarinone (ORF 16600,I).Although in many respects the structural requirements for the cardiotonic activity of II are similarto those of bemarinone, ceratin differences between the series were noted.Our structure-activity studies show that II is less sensitive to alkoxy-substitution effects than is I, and more significantly, 4-substitution of II by alkyl groups, halogen, or alkanecarboxylic acid derivatives enhances cardiotonic activity in II in contrast to I, wherein analogous substitution eliminated activity.A linear correlation between contractile force (CF) increase and cyclic nucleotide phosphodiesterase fraction III (PDE-III) inhibition by the title compounds was determined.The isoquinoline derivatives were characteristically short-acting cardiotonic agents with good potency and selectivity.