21544-81-0

Usage

Uses

Used in Pharmaceutical Industry:
4,6-DIMETHOXY-1H-INDOLE-2,3-DIONE is used as a potential active pharmaceutical ingredient for the development of new drugs due to its anti-inflammatory and anti-cancer properties. Its unique chemical structure and potential medicinal properties make it a promising candidate for further research and development in the pharmaceutical field.
Used in Research and Development:
4,6-DIMETHOXY-1H-INDOLE-2,3-DIONE is used as a subject of study for researchers and scientists interested in exploring its pharmacological and biological activities. Its unique chemical structure and potential medicinal properties provide a basis for investigating its therapeutic effects and applications in various medical conditions.

InChI:InChI=1/C10H9NO4/c1-14-5-3-6-8(7(4-5)15-2)9(12)10(13)11-6/h3-4H,1-2H3,(H,11,12,13)

Upstream product

• 79-37-8 oxalyl dichloride 
• 40891-33-6 3,5-dimethoxyaniline hydrochloride 
• 10272-07-8 3.5-dimethoxyaniline 

Downstream Products

• 178421-37-9 4,6-dimethoxy-3-hydroxy-3-phenylindolin-2-one 
• 74588-92-4 4,6-dimethoxy-1-(2-oxo-2-phenylethyl)indole-2,3-dione 
• 21577-57-1 2-amino-4,6-dimethoxybenzoic acid 
• 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 
• 628687-05-8 5-hydroxy-7-methoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 628687-02-5 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinethione 
• 628686-89-5 5,7-dimethoxy-3-(4-methoxyphenyl)-4(3H)-quinazolinone 
• 887468-88-4 7-methoxy-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-quinazoline-5-carbonitrile 

Relevant academic research and scientific papers

Synthesis and Preclinical Validation of Novel Indole Derivatives as a GPR17 Agonist for Glioblastoma Treatment

The discovery of a potential ligand-targeting G protein-coupled receptor 17 (GPR17) is important for developing chemotherapeutic agents against glioblastoma multiforme (GBM). We used the integration of ligand- and structure-based cheminformatics and exper

Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy

Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).

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.

A reassessment of mycophenolic acid as a lead compound for the development of inhibitors of chikungunya virus replication

Mycophenolic acid (MPA) has been previously reported as an inhibitor of the chikugunya virus (CHIKV) with an EC50 value of 0.2 μM. We used MPA as a lead compound designing and synthesizing a series of isatins and benzolactones in a typical medicinal chemistry program. The synthesis and testing of 19 derivatives produced compounds with no desired activity which prompted us to retest the lead compound, MPA. We can reveal that MPA shows no anti-CHIKV activity and therefore needs to be reassessed as a lead compound for this target.

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.

TREATMENT OF DISEASES BY EPIGENETIC REGULATION

The present disclosure provides non-naturally occurring polyphenol compounds that inhibit the bromodomain and extra terminal domain (BET) proteins. The disclosed compositions and methods can be used for treatment and prevention of cancer, including NUT midline carcinoma, Burkitt's Lymphoma, Acute Myelogenous Leukemia, and Multiple Myeloma; autoimmune or inflammatory diseases or conditions, and sepsis.

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 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.

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.