63920-75-2

Usage

Class

Benzoxazine derivatives

Physical Properties

White to off-white crystalline solid

Solubility

Insoluble in water, soluble in organic solvents

Primary Use

Building block in synthesis of pharmaceuticals, agrochemicals, and fine chemicals

Biological Activities

Antitumor, anti-malarial, antimicrobial

Potential Use

Organic electronic materials due to unique electronic and optical properties

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 21577-57-1 2-amino-4,6-dimethoxybenzoic acid 

Downstream Products

• 628686-84-0 2-amino-N-(2-fluoro-4-methoxyphenyl)-4,6-dimethoxybenzamide 
• 628686-85-1 2-amino-N-(3-fluoro-4-methoxy-phenyl)-4,6-dimethoxy-benzamide 
• 887468-62-4 2-amino-4,6-dimethoxy-N-(4-methoxyphenyl)benzamide 
• 887468-94-2 7-methoxy-3-(4-methoxy-phenyl)-5-methyl-3H-quinazoline-4-thione 
• 887468-75-9 7-methoxy-3-(4-methoxy-phenyl)-5-methyl-3H-quinazolin-4-one 
• 887468-86-2 5-amino-7-methoxy-3-(4-methoxy-phenyl)-3H-quinazolin-4-one 
• 628687-02-5 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinethione 
• 628686-89-5 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 628687-04-7 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinone 
• 887468-60-2 5,7-dimethoxy-3-(4-methoxy-phenyl)-8-methyl-3H-quinazolin-4-one 
• 628687-09-2 5-ethoxy-7-methoxy-3-(4-methoxyphenyl)-4(3H)-quinazoline 

Relevant academic research and scientific papers

Synthesis of Aza-Rocaglates via ESIPT-Mediated (3+2) Photocycloaddition

Synthesis of aza-rocaglates, nitrogen-containing analogues of the rocaglate natural products, is reported. The route features ESIPT-mediated (3+2) photocycloaddition of 1-alkyl-2-aryl-3-hydroxyquinolinones with the dipolarophile methyl cinnamate. A continuous photoflow reactor was utilized for photocycloadditions. An array of compounds bearing the hexahydrocyclopenta[b]indole core structure was synthesized and evaluated in translation inhibition assays.

ORGANIC COMPOUNDS

The present invention relates to quinazolinone compounds of the formula wherein R2, R3, R5, R6 R7 and R8 are as defined in the specification and in the claims, in free form or in salt form , processes for their preparation and their use as pharmaceuticals, particularly in the treatment of disorders ameliorated by administration of TRPV1 antagonists.

Synthesis and characterization of 3-arylquinazolinone and 3-arylquinazolinethione derivatives as selective estrogen receptor beta modulators

On the basis of the structure of genistein, a new series of 3-arylquinazolines was prepared and tested for their estrogen receptor (ER) α and β affinities. 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4(3H)- quinazolinone (1aa) acts as an agonist on both ER subtypes. It has 62-fold higher binding affinity [IC50(ERβ) = 179 nM] and 38-fold higher functional potency in a transcription assay [EC50(ERβ) = 76 nM] with ERβ than with ERα, thus improving upon the selectivity of genistein. All of the analogues showed preferential binding affinity for ERβ. Many are also more potent in activating transcription by ERβ than by ERα. Transformation of the C=O functionality at position 4 into a C=S group provided 5,7-dihydroxy-3-(4-hydroxyphenyl)-4(3H)-quinazolinethione (1ba), which acts as an agonist on both ER subtypes but has 56-fold higher binding affinity for ERβ over ERα [IC50(ERβ) = 47 nM] and 215-fold higher potency in the transcription assay [EC50(ERβ) = 13 nM]. These ERβ-selective compounds may represent valuable tools in understanding the differences in structure and biological function of ERβ and ERα.

C-5 SUBSTITUTED QUINAZOLINONE DERIVATIVES AS SELECTIVE ESTROGEN RECEPTOR BETA MODULATORS

The present application describes compounds according to Formula (I), wherein Q, R1, R2 and X are described herein, that are useful as Estrogen Receptor Beta (ERβ) modulators. Additionally, the present application describes pharmaceutical compositions containing the compounds according to Formula (I) and optionally additional therapeutic agents. Finally, the present application describes methods utilizing the compounds according to Formula (I) for modulating the function of ERβ in the treatment of diseases and disorders associated with ERβ such as, for example, bone disorders; cardiovascular diseases; hypercholesterolemia; hypertriglyceridemia; vasomotor disorders; urogenital disorders; prostatic hypertrophy; endometrial hyperplasia; cancer and central nervous system disorders, such as, neurodegenerative disorders.

3-ARYLQUINAZOLINE DERIVATIVES AS SELECTIVE ESTROGEN RECEPTOR BETA MODULATORS

Novel quinazoline derivatives possessing activity as estrogen receptor beta (ERβ) modulators are provided which have the general formula I wherein X is O or S; A and B are each independently CR'" or N; R, R' and R" are each independently hydrogen, alkyl, benzyl, p-methoxybenzyl, allyl, or Si(R4) 3, wherein at least one of R, R' and R" is hydrogen; R'" is hydrogen, halogen, CF3, OR5, S(O)nR6, NR7R8, cycloalkyl or alkyl; R1, R2 and R3 are each independently hydrogen, halogen, CF 3, OR5, S(O)nR6, NR7R8, cycloalkyl or alkyl; R4 is a alkyl; R5, R6, R7 and R8 in each functional group are each independently hydrogen, cycloalkyl or alkyl; and n is an integer from 0 to 2. In addition, a method is provided for preventing, inhibiting or treating the progression or onset of pathological conditions associated with the estrogen receptor and to pharmaceutical compositions containing such compounds. "

Oxamic acid derivatives

Anti-allergic agents of aromatic oxamic acid derivation present the following formula: STR1 in which A is a member selected from the group consisting of α-naphthyl, β-napthtyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals; and pharmaceutically acceptable salts thereof.

Oxamic acid derivatives

Anti-allergic agents of aromatic and heterocyclic oxamic acid derivation present the following formula: STR1 in which A is a member selected from the group consisting of 2-thiazolyl, 2-pyridyl, 2-pyridyl-N-oxide, 6-(lower)alkyl-2-pyridyl, 3-cyano-2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-pyrazinyl, α-naphthyl, β-naphthyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy(lower)alkoxy, 2-(lower alkoxy oxalyloxy) ethoxy, benzyloxy, N-mono-and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono-and di-lower alkylamino, phenylazo, carboxy, lower alkylcarbonyl, cyano, carb(lower)alkoxy, phenoxy(lower)alkoxy, lower alkoxyoxalamido and lower alkoxyoxalamidophenoxy radicals; B, when taken alone, is a member selected from the group consisting of --OH, lower alkoxy, --NH2, --NHOH, cyclohexyloxy and phenoxy; and Y is a member selected from the group consisting of oxygen and when taken with B and the carbon atom to which they are attached, forms the moiety STR2

Oxamic acid derivatives

Anti-allergic agents of aromatic oxamic acid derivation present the following formula: STR1 in which A is a member selected from the group consisting of α-naphthyl, β-naphthyl, phenyl, 2,6-di-chlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals; And pharmaceutically acceptable salts thereof.

Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions

Anti-allergic agents of aromatic oxamic acid derivation present the following formula: STR1 in which A is a member selected from the group consisting of α-naphthyl, β-naphthyl, phenyl, 2,6-dichlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy (lower)alkoxy, 2-(oxalyloxy) ethoxy, benzyloxy, N-mono- and di-lower alkylamino(lower)alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono and di lower alkylamino, carboxy, lower alkylcarbonyl, carb(lower)alkoxy, phenoxy(lower)alkoxy, and oxalamidophenoxy radicals; And pharmaceutically acceptable salts thereof.

Pyridyl oxamic acid derivatives and use in the prevention of allergic reactions

Anti-allergic agents of aromatic and heterocyclic oxamic acid derivation present the following formula: STR1 in which A is a member selected from the group consisting of 2-thiazolyl, 2-pyridyl, 2-pyridyl-N-oxide, 6-(lower)alkyl-2-pyridyl, 3-cyano-2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 2-pyrazinyl, α-naphthyl, βnaphthyl, phenyl, 2,6-dichlorophenyl, and substituted phenyl moieties containing from one to three substituents in any of the 2,3,4 and 5 positions of the phenyl ring, independently selected from the group consisting of lower alkyl, lower alkylthio, lower alkylsulfinyl, lower alkoxy, hydroxy(lower)-alkoxy, 2-(lower alkoxy oxalyloxy) ethoxy, benzyloxy, N-mono-and di-lower alkylamino(lower)-alkoxy, halo, sulfamyl, polyhalo(lower)alkyl, carbamyl, N-lower alkylcarbamyl, nitro, mono-and di-lower alkylamino, phenylazo, carboxy, lower alkylcarbonyl, cyano, carb(lower)alkoxy, phenoxy(lower)alkoxy, lower alkoxyoxalamido and lower alkoxyoxalamidophenoxy radicals; B, when taken alone, is a member selected from the group consisting of --OH, lower alkoxy, --NH2, --NHOH, cyclohexyloxy and phenoxy; and Y is a member selected from the group consisting of oxygen and when taken with B and the carbon atom to which they are attached, forms the moiety STR2