21577-57-1

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-4,6-DIMETHOXY-BENZOIC ACID is used as a key intermediate for the synthesis of N-(5-Chloro-1,3-benzodioxol-4-yl)-7-[2-(4-methylpiperazin-1-yl)ethoxy]-5-(tetrahydro-2H-pyran-4-yloxy)quinazolin-4-amine. 2-AMINO-4,6-DIMETHOXY-BENZOIC ACID is a highly selective, orally available, dual-specific c-Src/Abl kinase inhibitor, which has potential applications in the treatment of various cancers by targeting specific cellular pathways involved in tumor growth and progression.

InChI:InChI=1/C9H11NO4/c1-13-5-3-6(10)8(9(11)12)7(4-5)14-2/h3-4H,10H2,1-2H3,(H,11,12)

Upstream product

• 21544-81-0 4,6-dimethoxyindoline-2,3-dione 
• 10272-07-8 3.5-dimethoxyaniline 
• 890093-49-9 2-nitro-4,6-dimethoxybenzoic acid 
• 40891-33-6 3,5-dimethoxyaniline hydrochloride 

Downstream Products

• 57860-91-0 5,7-dimethoxy-2-(2-oxo-propyl)-benzo[d][1,3]oxazin-4-one 
• 159152-03-1 N-ethoxycarbonyl-9,11-dimethoxy-7-methyl-6a,7-dehydroanonaine 
• 63920-75-2 1,2-dihydro-5,7-dimethoxy-3,1-benzoxazine-2,4-dione 
• 379228-26-9 methyl 2-amino-4,6-dimethoxybenzoate 
• 628686-78-2 5,7-dimethoxy-2-ethyl-3,1-benzoxazine-4-one 
• 628686-77-1 5,7-dimethoxy-2-methyl-3,1-benzoxazine-4-one 
• 628686-92-0 5,7-dimethoxy-3-(4-methoxyphenyl)-2,4-(1H,3H)-quinazolinedione 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel HDAC inhibitors with improved pharmacokinetic profile in breast cancer

The dysfunction of histone deacetylase (HDACs) is closely related to tumorigenesis and development, which has been emerged as an attractive drug design target for cancer therapy. In the present study, we designed and synthesized a series of novel HDAC inhibitors using a substituted quinazoline as the capping group and attaching 3, 5-dimethylbenyl as a potential metabolic site protector. 23g and 23h were demonstrated potent HDAC inhibitory activities and anti-proliferative effects against MDA-MB-231 cells. In addition, 23g and 23h both could significantly increase the acetylation level of intracellular proteins, especially in α-Tubulin and HSP90. 23g and 23h displayed a slight different anti-tumor mechanism, 23g mainly induced apoptosis while 23h induced obviously ER-Stress. Furthermore, 23g and 23h both induced autophagy and migration inhibition. In pharmacokinetics assay, 23g showed a significant improvement of pharmacokinetic profile for oral administration. Additionally, 23g presented more potent anti-proliferation and anti-migration activity than SAHA in zebrafish MDA-MB-231 cell line-derived xenograft model. Together, these results demonstrate that 23g is a novel oral HDAC inhibitor with a potential capacity of treating breast cancer.

Structure-based design, synthesis and in vitro antiproliferative effects studies of novel dual BRD4/HDAC inhibitors

Histone acetylation marks play important roles in controlling gene expressions and are removed by histone deacetylases (HDACs). These marks are read by bromodomain and extra-terminal (BET) proteins, whose targeted inhibitors are under clinical investigation. BET and HDAC inhibitors have been demonstrated to be synergistically killing in Mycinduced murine lymphoma. Herein, we combine the inhibitory activities of BET and HDAC into one molecule through structure-based design method and evaluate its function. The majority of these synthesized compounds showed inhibitory activity against second bromdomains(BRD) of BRD4 and HDAC1. Among them, 16ae presented anti-proliferative effects against human acute myelogenous leukemia (AML) cell lines in vitro, and 16ae is confirmed to reduce the expression of Myc by Western blot analysis. Those results indicated that 16ae is a potent dual BRD4/HDAC inhibitor and deserves further investigation.

Used for the prevention and treatment of cardiovascular diseases

The invention relates to compounds that can be used for adjusting the expression of apolipoprotein A-I (ApoA-I) and usage of the compounds in treating and preventing cardiovascular diseases and related diseases, including the disorder related to cholesterol or lipids such as atherosclerosis.

Characterization, synthesis and self-aggregation of (-)-alternarlactam: A new fungal cytotoxin with cyclopentenone and isoquinolinone scaffolds

(-)-Alternarlactam [(-)-1], a new promising cytotoxin against two human cancer cell lines, was isolated from an endophyte culture and synthesized (along with (+)-1) from readily available starting materials. The absolute configuration, chirality-activity relevance and self-aggregation of (-)-1 were assigned by a combination of synthetic, spectroscopic and computational approaches. The full characterization of the new fungal cytotoxin may provide valuable information in the discovery of new antitumor agents. Double the framework: The absolute configuration, chirality-activity relevance and self-aggregation of (-)-alternarlactam [(-)-1], a cytotoxin from Alternaria sp. HG1 culture with double antitumor pharmacophores in a new framework, were assigned by a combination of synthetic, spectroscopic and computational approaches. Copyright

COMPOUNDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES

The present disclosure relates to compounds, which are useful for regulating the expression of apolipoprotei? A-I (ApoA-l), and their use for the treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis.

COMPOUNDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASES

The present disclosure relates to compounds, which are useful for regulating the expression of apolipoprotein A-I (ApoA-I), and their use for treatment and prevention of cardiovascular disease and related disease states, including cholesterol- or lipid-related disorders, such as, for example, atherosclerosis.

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.

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. "