23042-75-3

Usage

Uses

Used in Chemical Synthesis:
N-(2,4-dimethoxyphenyl)acetamide is used as a reactant for the synthesis of regioselective halogenation of aromatic compounds. Its presence in the reaction mixture aids in achieving a specific orientation of the halogen atom on the aromatic ring, which is crucial for the subsequent reactions and the desired product's properties.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(2,4-dimethoxyphenyl)acetamide may be utilized as an intermediate in the synthesis of various drugs and pharmaceutical compounds. Its unique structure can be further modified to create molecules with specific biological activities, contributing to the development of new medications.
Used in Material Science:
The compound may also find applications in material science, particularly in the development of novel materials with tailored properties. Its ability to participate in specific chemical reactions can lead to the creation of new polymers, coatings, or other materials with improved characteristics.

InChI:InChI=1/C10H13NO3/c1-7(12)11-9-5-4-8(13-2)6-10(9)14-3/h4-6H,1-3H3,(H,11,12)

Upstream product

• 26053-96-3 4-acetoxy-4'-methoxyazobenzene 
• 75-36-5 acetyl chloride 
• 2735-04-8 2,4-Dimethoxyaniline 
• 72-89-9 acetylcoenzyme A 
• 61638-01-5 4-Amino-3-methoxyphenol 
• 106063-48-3 4-benzenesulfonic acid 
• 150-19-6 O-methylresorcine 
• 108-24-7 acetic anhydride 
• 128317-40-8 N-methoxy-N-(4-methoxyphenyl)acetamide 
• 75-18-3 dimethylsulfide 
• 5307-06-2 N-(4-hydroxy-2-methoxyphenyl)acetamide 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 99075-67-9 thioacetic acid-(2,4-dimethoxy-anilide) 
• 76030-55-2 (2,4-dimethoxyphenyl)methanamine 
• 857950-16-4 2,4-dimethoxy-5-nitroacetanilide 
• 2735-04-8 2,4-Dimethoxyaniline 
• 78149-75-4 2-(2,4-Dimethoxy-5-(methylcarboxamido)benzoyl)-4-methyl-4-cyclohexenecarboxylic Acid 
• 562869-42-5 C₁₉H₂₂N₂O₅S 
• 1411995-57-7 C₂₅H₂₄N₂O₈S 
• 1411995-59-9 C₂₂H₂₆N₆O₅S 
• 1411995-62-4 C₂₇H₂₃N₃O₆S 
• 1411995-63-5 C₂₅H₂₆FN₃O₅S 
• 1411995-65-7 C₂₆H₂₆N₄O₅S 
• 1375463-31-2 C₂₁H₂₄N₂O₇S 
• 1361928-31-5 C₂₂H₂₆N₂O₇S 
• 1361928-25-7 C₂₀H₂₄N₂O₅S 

Relevant academic research and scientific papers

Evaluation of DIMBOA analogs as antifeedants and antibiotics towards the aphid Sitobion avenae in artificial diets

A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.

New Facile Synthesis of 7-Hydroxy-6-amino-4-substituted Benzopyran-2-ones

A new facile synthesis of 6-amino-7-hydroxy-4-substituted benzopyranones is described through the von Pechmann reaction. The yields obtained were high, and the proposed methodology leads to pure products. The selectivity of formation of the desired products can be attributed to the formation of an intramolecular hydrogen bond, which leads to reduced reactivity of the 2-hydroxyl group.

Isoxazole sulfonamides compound with BRD4 inhibitory activity and preparation method and application thereof

The invention provides an isoxazole sulfonamide compound with BRD4 inhibitory activity or a pharmaceutically acceptable salt thereof, and the compound has the structural formula shown in the general formula (I). The invention further provides an application of the compound or a pharmaceutically acceptable salt or the pharmaceutical composition in preparation of a medicament for preventing or treating cancer related to BRD4, wherein the cancer comprises leukemia. The lymphoma, myeloma, lung cancer, prostate cancer, pancreatic cancer, colon cancer, breast cancer, liver cancer, gastric cancer, and the like. The invention provides a novel BRD4 inhibitor, and experiments prove that the novel compound has a 3 - ethyl benzo [d] isoxazole sulfonamide structure and has a good BRD4 protein inhibition effect and an in-vitro tumor cell inhibition effect. The compounds can also effectively inhibit the expression of c-Myc oncogenes.

Synthesis, evaluation and in silico studies of novel BRD4 bromodomain inhibitors bearing a benzo[d]isoxazol scaffold

Abstract: The BRD4 protein is associated with various diseases, which has been an attractive target for the treatment of cancer and inflammation. This paper is a follow-up to our previous studies, in which we report the structure-based design, synthesis, and evaluation of a new class of small-molecule BRD4 bromodomain inhibitors bearing a benzo[d]isoxazol scaffold. The SARs focused on exploration of the 2′ or 3′ position to afford novel inhibitors that may avoid potential metabolically unstable site. The most potent inhibitor 13f exhibited high binding affinity to BRD4(1) with a ΔTm value of 7.8 °C as evaluated in thermal shift assay (TSA). The potent activity was also demonstrated by a peptide competition assay with an IC50 value of 0.21?μM. The docking studies revealed the binding mode of the compounds with the active site of BRD4(1). In addition, in silico predictions indicated that these compounds possessed good drug-likeness and pharmacokinetic profile. Graphic abstract: This paper is a follow-up to our previous studies, in which we report the structure-based design,synthesis, and evaluation of a new class of small-molecule BRD4 bromodomain inhibitors bearing a benzo[d]isoxazolscaffold.[Figure not available: see fulltext.].

Selective, Catalytic, and Metal-Free Coupling of Electron-Rich Phenols and Anilides Using Molecular Oxygen as Terminal Oxidant

Selective oxidative homo- and cross-coupling of electron-rich phenols and anilides was developed using nitrosonium tetrafluoroborate as a catalyst. Oxidative coupling of phenols revealed unusual selectivities, which translated into the unprecedented synthesis of inverse Pummerer-type ketones. Mechanistic studies suggest that oxidative coupling of phenols and anilides shares a common pathway via homolytical heteroatom-hydrogen bond cleavage. Nitrosonium salt catalysis was applied for cross-dehydrogenative coupling initiated by generation of heteroatom-centered radicals.

Structure-Based Discovery and Optimization of Benzo [d] isoxazole Derivatives as Potent and Selective BET Inhibitors for Potential Treatment of Castration-Resistant Prostate Cancer (CRPC)

The bromodomain and extra-terminal (BET) family proteins have gained increasing interest as drug targets for treatment of castration-resistant prostate cancer (CRPC). Here, we describe the design, optimization, and evaluation of benzo[d]isoxazole-containing compounds as potent BET bromodomain inhibitors. Cocrystal structures of the representative inhibitors in complex with BRD4(1) provided solid structural basis for compound optimization. The two most potent compounds, 6i (Y06036) and 7m (Y06137), bound to the BRD4(1) bromodomain with Kd values of 82 and 81 nM, respectively. They also exhibited high selectivity over other non-BET subfamily members. The compounds potently inhibited cell growth, colony formation, and the expression of AR, AR regulated genes, and MYC in prostate cancer cell lines. Compounds 6i and 7m also demonstrated therapeutic effects in a C4-2B CRPC xenograft tumor model in mice. These potent and selective BET inhibitors represent a new class of compounds for the development of potential therapeutics against CRPC.

A kind of benzo [d] different wicked zuozuo apperception compound and use thereof

The invention relates to the technical field of chemical medicine, and particularly discloses a benzo[d]isoxazole compound shown as a general formula (A) and application thereof. The compound can effectively inhibit bromodomain of BET family proteins so as to block interaction between the BET family proteins and chromatin histone to adjust genetic transcription, cause changing of a downstream signal path and exert important influence on various diseases, so that the compound and a combination thereof can be used for preparing medicine for treating or preventing diseases like tumorigenesis, inflammation, viral infection, cell proliferation disorder, autoimmune diseases and septicemia.

A versatile biosynthetic approach to amide bond formation

The development of versatile and sustainable catalytic strategies for amide bond formation is a major objective for the pharmaceutical sector and the wider chemical industry. Herein, we report a biocatalytic approach to amide synthesis which exploits the diversity of Nature's amide bond forming enzymes, N-acyltransferases (NATs) and CoA ligases (CLs). By selecting combinations of NATs and CLs with desired substrate profiles, non-natural biocatalytic pathways can be built in a predictable fashion to allow access to structurally diverse secondary and tertiary amides in high yield using stoichiometric ratios of carboxylic acid and amine coupling partners. Transformations can be performed in vitro using isolated enzymes, or in vivo where reactions rely solely on cofactors generated by the cell. The utility of these whole cell systems is showcased through the preparative scale synthesis of a key intermediate of Losmapimod (GW856553X), a selective p38-mitogen activated protein kinase inhibitor.

METHOD FOR SYNTHESISING AMIDES

The present invention relates to a method for synthesising amides that is of general applicability. The method may be performed in vitro or in vivo. Cell lines for use in the in vivo methods also form aspects of the invention. The method for synthesising a non-natural amide comprises: a. reaction of a carboxylic acid with a naturally occurring CoA ligase or a variant thereof; and b. reaction of the product of step a with an amine in the presence of a naturally occurring acyltransferase or a variant thereof; with the proviso that where the CoA ligase and acyltransferase are both naturally occurring, they are not derived from the same source species and do not act sequentially in a metabolic pathway; and with the proviso that the non-natural product is not N-(E)-p-coumaroyl-3-hydroxyanthranilic acid or N-(E)-p-caffeoyl-3-hydroxyanthranilic acid. Further, a method for producing an active pharmaceutical ingredient by the aforementioned method and host cells for carrying out said methods are envisaged.

Aerobic oxidative homocoupling reaction of anilides using heterogeneous metal catalysts

We have developed a heterogeneous catalytic oxidative homocoupling reaction of dimethoxyanilides under an oxygen atmosphere. The resulting homo-dimers are useful for the construction of heterocycles, demonstrating the potential of heterogeneous metal catalysts.