63920-73-0

Basic information

• Product Name: 2-aMino-4,6-diMethoxybenzaMide
• Synonyms: 2-aMino-4,6-diMethoxybenzaMide;Benzamide, 2-amino-4,6-dimethoxy-;4,6-Dimethoxyanthranilamide
• CAS NO: 63920-73-0
• Molecular Formula: C₉H₁₂N₂O₃
• Molecular Weight: 196
• Mol File: 63920-73-0.mol

Chemical Properties

• Boiling Point: 331.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 15.70±0.50(Predicted)
• CAS DataBase Reference: 2-aMino-4,6-diMethoxybenzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-aMino-4,6-diMethoxybenzaMide(63920-73-0)
• EPA Substance Registry System: 2-aMino-4,6-diMethoxybenzaMide(63920-73-0)

Safety Data

• Hazardous Substances Data: 63920-73-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4,6-dimethoxybenzamide is used as a potential active pharmaceutical ingredient for its anti-inflammatory and analgesic effects. Its pharmacological properties make it a candidate for the development of new drugs to treat pain and inflammation.
Used in Organic Synthesis:
2-Amino-4,6-dimethoxybenzamide is used as a building block in organic synthesis for the creation of various chemical compounds. Its unique structure and functional groups allow for the synthesis of a wide range of organic molecules.
Used in Agrochemical Development:
2-Amino-4,6-dimethoxybenzamide is used in the development of agrochemicals, where its potential biological activities can be harnessed for applications in agriculture, such as pest control or crop protection.
Used in Research and Development:
2-Amino-4,6-dimethoxybenzamide is used in various fields of research and development, including medicinal chemistry, material science, and chemical engineering, due to its versatile chemical properties and potential applications.

Upstream product

• 1599437-13-4 N-(2-bromo-3,5-dimethoxybenzene)-2,2,2-trifluoroacetamide 
• 85657-94-9 N-(3,5-dimethoxyphenyl)-2,2,2-trifluoroacetamide 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 99-10-5 3,5-Dihydroxybenzoic acid 
• 1545025-44-2 2-amino-4,6-dimethoxybenzonitrile 
• 1599437-14-5 2-cyano-3,5-dimethoxytrifluoroacetanilide 
• 10272-07-8 3.5-dimethoxyaniline 
• 40891-33-6 3,5-dimethoxyaniline hydrochloride 
• 21544-81-0 4,6-dimethoxyindoline-2,3-dione 
• 21577-57-1 2-amino-4,6-dimethoxybenzoic acid 
• 63920-75-2 1,2-dihydro-5,7-dimethoxy-3,1-benzoxazine-2,4-dione 

Downstream Products

• 1044870-86-1 N-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenyl)-2-hydroxyacetamide 
• 1044871-48-8 N-{2-[4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy]ethyl}-4-methoxybenzene-1-sulfonamide 
• 1044871-62-6 N-(2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)ethyl)-4-methyl benzamide 
• 1044871-74-0 1-(2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy)acetyl)-3-methylurea 
• 1044871-31-9 2-(4-amino-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one 
• 1044871-54-6 2-(4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methoxyphenoxy)acetic acid 
• 1044871-29-5 5,7-dimethoxy-2-(4-methoxy-3,5-dimethylphenyl)quinazolin-4(3H)-one 
• 1044871-46-6 2-(4-(2-aminoethoxy)-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one 
• 1044871-45-5 1-N-{2-[4-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-2,6-dimethylphenoxy]ethyl}-2-N-methylphthalic acid diamide 
• 1610372-28-5 4-(6-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-3-(2-hydroxyethoxy)pyridin-2-yl)-N,N,3-trimethylbenzamide 
• 1610372-43-4 2'-(azetidin-3-yloxy)-5'-(5,7-dimethoxy-4-oxo-3,4-dihydroquinazolin-2-yl)-[1,1'-biphenyl]-4-carbonitrile 
• 1044871-14-8 5,7-dimethoxy-2-(4-(2-methoxyethoxy)-3,5-dimethylphenyl)quinazolin-4(3H)-one 
• 1044872-55-0 2-[4-(2-benzyloxyethoxy)-3,5-dimethyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one 
• 1044872-54-9 2-[3-(2-hydroxy-ethyl)-4-methoxymethoxy-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one 

Relevant articles and documents

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.

Design, synthesis and biological evaluation of hypolipidemic compounds based on BRD4 inhibitor RVX-208

Bromodomain-containing protein 4 (BRD4) is a new therapeutic target for the treatment of diseases including cardiovascular diseases, cancer, inflammation and central nervous system (CNS) disorders. In this study, we introduced the pharmacophore of fibrates to a BRD4 inhibitor, RVX-208, to design dual-active hypolipidemic compounds, and found that some of new analogues showed favorable hypolipidemic activities. Synthetic accessibility towards this class of compounds optimized RVX-208 as well as would supply more thoughts on hypolipidemic drugs.

Based on BRD4 inhibitor RVX - 208 of the derivative and its preparation method and application (by machine translation)

The invention discloses a method based on BRD4 inhibitor RVX - 208 of the derivative and its preparation method and application. Derivatives of the structure shown in formula I. The preparation method comprises: type 8 compound of formula 9 compound reaction, [...] 10 compound; type 10 compounds with malonic acid, d di-acid or fifth heavenly stem II acid after the reaction, with vinyl carbonate, 2 - halo of isobutyric acid or 4 - halo [...] butyric acid reaction; or, the type 10 compound directly with ethylene carbonate, 2 - halo of isobutyric acid or 4 - halo [...] butyric acid reaction. The invention also provides its application. The present invention provides based on BRD4 inhibitor RVX - 208 of the derivatives, can improve the activity or at the same time reducing cholesterol lowering cholesterol and triglyceride levels. (by machine translation)

NITRIC OXIDE-RELEASING PRODRUG MOLECULE

Provided are a type of compounds that can be used for treating cardiovascular diseases and compositions containing the compounds. The compounds and the compositions can improve lipid metabolism disorders by increasing high-density lipoprotein cholesterol in blood; in addition, the compounds and the compositions can also release nitric oxide, and reduce the onset risk of cardiovascular diseases by means of relaxing blood vessels, lowering blood pressure, inhibiting platelet adhesion and aggregation and maintaining vascular tension, and thus play an important role in preventing and treating the occurrence and development of cardiovascular diseases.

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.

PROCESSES FOR THE SYNTHESIS OF 2-AMINO-4,6-DIMETHOXYBENZAMIDE AND OTHER BENZAMIDE COMPOUNDS

This invention provides a method for the synthesis of a 2-amino-4,6-dimethoxybenzamide and other benzamides of Compound I: wherein R1, R2, R3, and R4 each independently represent a hydrogen, a C1-C6 alkyl, or a C1-C6 alkoxy; and wherein R6 and R7 each independently represent a hydrogen, a C1-C6 alkyl, a protecting group, or a directing group.

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.

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.