98300-41-5

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 30, p. 1421, 1987 DOI: 10.1021/jm00391a026

Upstream product

• 98300-40-4 2',3'-dimethoxy-6'-nitroacetophenone 
• 107738-33-0 2'-acetyl-3',4'-dimethoxy-2,2-dimethylpropioanilide 
• 107738-34-1 N-(3,4-dimethoxyphenyl)-2,2-dimethylpropanamide 
• 107738-32-9 2-(1,1-dimethylethyl)-5,6-dimethoxy-4H-3,1-benzoxazin-4-one 
• 107738-35-2 2'-carboxy-3',4'-dimethoxy-2,2-dimethylpropioanilide 
• 6315-89-5 3,4-dimethoxyaniline 
• 72517-26-1 2,3-dimethoxy-6-nitrobenzoic acid 
• 98263-19-5 2,3-dimethoxy-6-nitrobenzoyl chloride 
• 103483-20-1 diethyl 2-(2,3-dimethoxy-6-nitrobenzoyl)-propanedioate 
• 2531-63-7 5,6-dimethoxy-2-nitrobenzaldehyde 
• 2426-60-0 2-Hydroxy-3-methoxy-6-nitrobenzaldehyde benzenesulfonate 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 111042-36-5 2-Hydroxy-3-methoxy-6-nitrobenzaldehyde, sodium salt 
• 5653-62-3 2,3-dimethoxybenzonitrile 

Downstream Products

• 98300-42-6 6'-(N-2-carbethoxyethylamino)-2',3'-dimethoxyacetophenone 
• 1256037-09-8 N-(2-acetyl-3,4-dimethoxyphenyl)-4-fluorobenzamide 
• 1256037-07-6 N-(2-acetyl-3,4-dimethoxyphenyl)-3-fluorobenzamide 
• 1256037-05-4 N-(2-acetyl-3,4-dimethoxyphenyl)-2-fluorobenzamide 
• 1350903-36-4 N-(2-acetyl-3,4-dimethoxyphenyl)selenophene-2-carboxamide 
• 1350903-38-6 N-(2-acetyl-3,4-dimethoxyphenyl)-5-methylselenophene-2-carboxamide 
• 1350903-41-1 N-(2-acetyl-3,4-dimethoxyphenyl)selenophene-3-carboxamide 
• 1256037-23-6 2-(2-fluorophenyl)-5,6-dimethoxyquinolin-4-one 
• 1256037-40-7 2-(2-fluorophenyl)-5-hydroxy-6-methoxyquinolin-4-one 
• 92210-43-0 5,6-dimethoxy-4-methyl-2(1H)-quinazolinone 
• 139439-32-0 N-(2-Acetyl-3,4-dimethoxy-phenyl)-2,2,2-trifluoro-acetamide 
• 103483-21-2 6-Carboethoxyamino-2,3-dimethoxyacetophenone 
• 103483-22-3 5,6,5',6'-Tetramethoxy-4,4'-dimethyl-3',4'-dihydro-1'H-[1,4']biquinazolinyl-2,2'-dione 

Relevant academic research and scientific papers

Photo-Fries rearrangement of aryl acetamides: Regioselectivity induced by the aqueous micellar green environment

Photochemical reactions tend to give more than one photoproduct. However, such a reaction can be a powerful synthetic tool when it is possible to conduct it in regioselective conditions yielding a single photoproduct. Water-surfactant solutions as reaction media can be considered as an approach in this context because they show products with different features than those from isotropic solutions. Here we describe results obtained from studying the effect on the prototypical photoreaction, known as the photo-Fries reaction of several substituted acetanilides and α-naphthyl acetamide within surfactant micelles (ionic and non-ionic micelles). This reaction involves homolytic cleavage of a C-N bond to yield a singlet radical pair. The surfactant micelles control the rotational and translational mobility of the radical pair, resulting in noticeable photoproduct selectivity.

SYNTHESIS AND ANTICANCER ACTIVITY OF ARYL AND HETEROARYL-QUINOLIN DERIVATIVES

A compound of Formula I is disclosed as follows: or a pharmaceutically acceptable salt, prodrug, solvate, or metabolite thereof, wherein R is hydrogen, P(═O)(OH)2, P(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, P(═O)(OH)(OM), P(═O)(OM)2, P═O(O2M), S(═O)(OH)2, S(═O)(O(C1-C18)alkylene(C6-C20)aryl)2, S(═O)(OH)(OM), S(═O)(OM)2; M is a monovalent or divalent metal ion, or alkylammonium ion; W is (C6-C20)aryl, (C6-C20)heteroaryl, (C1-C18)alkyl(C6-C20)aryl, (C1-C18)alkyl(C6-C20)heteroaryl, hydroxy(C6-C20)aryl, hydroxy(C6-C20)heteroaryl, (C1-C18)alkoxy(C6-C20)aryl, (C1-C18)alkoxy(C6-C20)heteroaryl, (C1-C18)alkylenedioxy(C6-C20)aryl, (C1-C18)alkylenedioxy(C6-C20)heteroaryl, halo(C6-C20)aryl, halo(C6-C20)heteroaryl, (C1-C18)alkylamino(C6-C20)aryl, (C1-C18)alkylamino(C6-C20)heteroaryl, (C1-C18)cycloalkylamino(C6-C20)aryl, or (C1-C18)cycloalkylamino(C6-C20)heteroaryl, and their OR8 substutes; R5 is (C1-C18alkoxy, hydrogen, hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or OR8, or R5 and R6 are (C1-C18)dioxy provided that R7 is hydrogen; R6 is hydroxyl, O—(C1-C18)alkyl(C6-C20)aryl, halo or ORR, (C1-C18)alkoxy, (C1-C18)alkylamino, or (C1-C18)cycloalkylamino, or R6 and R7 are (C1-C18)dioxy provided that R5 is hydrogen; R7 is hydrogen, halo or OR8, hydroxyl, or O—(C1-C18)alkyl(C6-C20)aryl; and R8 is P(═O)(OH)2, P(═O)(O(C1-C18)alkyl(C6-C20)aryl)2, P(═O)(OH)(OM), or P(═O)(OM)2, P═O(O2M).

Synthesis of the cardiotonic bemarinone, 5,6-dimethoxy-4-methyl-2(1H)-quinazolinone, utilizing a direct metalation approach

Several methods for the synthesis of bemarinone, 5,6-dimethoxy-4-methyl-2(1H)-quinazolinone, were explored with the most successful being a directed metalation route. Details of the lithiation and the subsequent reaction with electrophiles of 3',4'-dimeth

Process for preparing 2-acyl-3,4-dialkoxyanilines

A process for preparing 2-acyl-3,4-dialkoxyanilines is described. The 2-acyl-3,4-dialkoxyanilines are useful intermediates in the preparation of 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones. The substituted quinazolinones are active as cardiotonic agents.

Process for preparing 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones

A method for preparing 5,6-dialkoxy-4-alkyl-quinazolinones is described. The 5,6-dialkoxy-4-alkyl-quinazolinones are active cardiotonic agents.

Synthesis and Cardiotonic Activity of a Series of Substituted 4-Alkyl-2(1H)-quinazolinones

The synthesis, cardiac fraction III cyclic nucleotide phosphodiesterase (PDE-III) inhibition, and positive inotropic activity of a series of 2(1H)-quinazolinones are reported.A general synthesis of the series involved the cyclization of 2-aminoacetophenones with potassium cyanate in acetic acid.Modifications at the 4-position of the quinazoline nucleus were best achieved by formation of the intermediate N1-acyl-N3-phenylurea from the substituted phenyl isocyanate and appropriate carboxamide.PPA was used to ring close to the quinazoline product.Generally the SAR for the series paralleled the five-point model previously published for PDE-III inhibition.The most active analogue of the series was 5,6-dimethoxy-4-methyl-2(1H)-quinazolinone (1) (ORF 16600), which had about twice the intravenous potency of amrinone.Compound 1 is currently under development as an orally active cardiotonic.

3,4-Dialkoxy-2-alkylcarbonyl analino compounds

A process for preparing 4-alkyl-2(1H)quinazolinone-1-alkanoic acid derivatives is described. The 4-alkyl-2(1H)quinazolinones are useful as cardiovascular agents.