379228-26-9

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 2-amino-4,6-dimethoxybenzoate is used as a reagent for the preparation of C-5 substituted anilinoquinazolines. These anilinoquinazolines are known to act as inhibitors of epidermal growth factor receptor tyrosine kinase (EGFR-TK), which plays a crucial role in cell signaling and has been implicated in various cancers. By inhibiting EGFR-TK, these compounds can potentially help in the treatment of cancer.

Upstream product

• 186581-53-3 diazomethane 
• 21577-57-1 2-amino-4,6-dimethoxybenzoic acid 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 40891-33-6 3,5-dimethoxyaniline hydrochloride 
• 21544-81-0 4,6-dimethoxyindoline-2,3-dione 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 379228-27-0 5,7-dimethoxyquinazolin-4(3H)-one 
• 628686-92-0 5,7-dimethoxy-3-(4-methoxyphenyl)-2,4-(1H,3H)-quinazolinedione 
• 628687-03-6 5,7-dimethoxy-3-(4-methoxyphenyl)-2-(methylthio)-4(3H)-quinazolinone 
• 628686-91-9 2-mercapto-5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 331662-65-8 5,7-dimethoxy-4-hydroxy-3-quinolinecarbonitrile 
• 331662-73-8 4-chloro-5,7-dimethoxy-3-quinolinecarbonitrile 
• 628686-91-9 2-mercapto-5,7-dimethoxy-3-(4-methoxyphenyl)-2,3-dihydro-4-(1H)-quinazolinone 
• 379228-25-8 4-[(2-chloro-5-methoxyphenyl)amino]-7-methoxyquinazolin-5-ol 
• 692726-14-0 (2-chloro-5-methoxy-phenyl)-(5,7-dimethoxy-quinazolin-4-yl)-amine 
• 884340-91-4 4-chloro-5,7-bis(methyloxy)quinazoline 

Relevant academic research and scientific papers

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.

N-(5-chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy] -5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine, a novel, highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor

Src family kinases (SFKs) are nonreceptor tyrosine kinases that are reported to be critical for cancer progression. We report here a novel subseries of C-5-substituted anilinoquinazolines that display high affinity and specificity for the tyrosine kinase domain of the c-Src and Abl enzymes. These compounds exhibit high selectivity for SFKs over a panel of recombinant protein kinases, excellent pharmacokinetics, and in vivo activity following oral dosing. N-(5-Chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5- (tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine (AZD0530) inhibits c-Src and Abl enzymes at low nanomolar concentrations and is highly selective over a range of kinases. AZD0530 displays excellent pharmacokinetic parameters in animal preclinically and in man (t1/2 = 40 h). AZD0530 is a potent inhibitor of tumor growth in a c-Src-transfected 3T3-fibroblast xenograft model in vivo and led to a significant increase in survival in a highly aggressive, orthotopic model of human pancreatic cancer when dosed orally once daily. AZD0530 is currently undergoing clinical evaluation in man.

QUINAZOLINE DERIVATIVES FOR THE TREATMENT OF TUMOURS

The invention concerns quinazoline derivatives of Formula (I) wherein each of Q1, Z, m, R1, R2, R3 and Q2 have any of the meanings defined in the description; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use as an anti-invasive agent in the containment and/or treatment of solid tumour disease

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. "