5813-86-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxybenzamide is used as an inhibitor of ADP-ribosyltransferase for its potential role in the development of therapeutic agents targeting this enzyme. ADP-ribosyltransferases are involved in various cellular processes, and their inhibition can have significant implications in treating certain diseases.
Additionally, 3-Methoxybenzamide is used as a weak inhibitor of the essential bacterial cell division protein FtsZ. This application is relevant in the development of new antibiotics, as inhibiting FtsZ can disrupt bacterial cell division and potentially lead to the eradication of the bacteria.
Used in Antistaphylococcal Applications:
3-Methoxybenzamide and its alkyl derivatives are used as potent antistaphylococcal compounds, particularly against Staphylococcus aureus. These compounds exhibit suboptimal drug-like properties, but their potent activity against this pathogen makes them a valuable starting point for the development of new antistaphylococcal drugs.

Biological Activity

3-Methoxybenzamide (3-MBA), an inhibitor of ADP-ribosyltransferase (ADPRTs) and PARP, inhibits cell division in Bacillus subtilis, leading to filamentation and eventually lysis of cells. 3-Methoxybenzamide (3-MBA) enhances in vitro plant growth, microtuberization, and transformation efficiency of blue potato (Solanum tuberosum L. subsp. andigenum).

InChI:InChI=1/C8H9NO2/c1-11-7-4-2-3-6(5-7)8(9)10/h2-5H,1H3,(H2,9,10)

Upstream product

• 38489-80-4 (E)-3-methoxybenzaldoxime 
• 1711-05-3 m-anisoyl chloride 
• 1527-89-5 3-methoxybenzonitrile 
• 586-38-9 3-Methoxybenzoic acid 
• 57-13-6 urea 
• 58296-98-3 3-methoxybenzaldehyde N,N-dimethylhydrazone 
• 33341-67-2 N-Chlor-3-methoxy-benzamid 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 6971-51-3 3-methoxybenzyl alcohol 
• 100-84-5 1-methoxy-3-methyl-benzene 
• 591-31-1 3-methoxy-benzaldehyde 
• 766-85-8 3-methoxy-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 92849-70-2 3-methoxy-N-phenylbenzimidamide 

Downstream Products

• 136116-43-3 1-(m-methoxyphenyl)-1-octanone 
• 857165-59-4 1-(3-methoxy-phenyl)-tridecan-1-one 
• 172264-98-1 1-(3-methoxyphenyl)nonan-1-one 
• 342423-70-5 1-(3-methoxyphenyl)-hexan-1-one 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 1527-89-5 3-methoxybenzonitrile 
• 64739-71-5 3-methoxy-cyclohexa-2,5-dienecarboxylic acid amide 
• 57764-61-1 N-chloroacetyl-3-methoxy-benzamide 
• 6266-57-5 1,2-bis(3-methoxyphenyl)ethan-1-one 
• 586-38-9 3-Methoxybenzoic acid 
• 7664-41-7 ammonia 
• 57764-73-5 6,6-dimethoxy-5-(3-methoxy-phenyl)-4-oxa-1-aza-bicyclo[3.2.0]heptan-2-one 
• 57764-74-6 7b-(3-methoxy-phenyl)-(4ar,7ac,7bξ)-7a,7b-dihydro-4aH-furo[3',2':3,4]azeto[2,1-b]oxazol-3-one 
• 57764-65-5 2-(3-methoxy-phenyl)-oxazol-4-one 

Relevant academic research and scientific papers

Visible light-mediated synthesis of amides from carboxylic acids and amine-boranes

Here, a photocatalytic deoxygenative amidation protocol using readily available amine-boranes and carboxylic acids is described. This approach features mild conditions, moderate-to-good yields, easy scale-up, and up to 62 examples of functionalized amides with diverse substituents. The synthetic robustness of this method was also demonstrated by its application in the late-stage functionalization of several pharmaceutical molecules.

Nano-construction of CuO nanorods decorated with g-C3N4 nanosheets (CuO/g-C3N4-NS) as a superb colloidal nanocatalyst for liquid phase C[sbnd]H conversion of aldehydes to amides

Herein, we describe an intelligent strategy to fabricate nanosheets of graphitic carbon nitride (g-C3N4) decorated with nanorods copper oxide (CuO NRs). Then, the catalytic activity of CuONRs/g-C3N4-NS was developed for the synthesis of primary amides in water. The morphology of CuO and its synergetics effect with nanosheets g-C3N4 a major role in the yield of products. Furthermore, hydroxylamine hydrochloride (NH2OH·HCl) due to availability and affordability was used as a suitable substitute for ammonia source. The findings demonstrate that this layer nanostructure is a superb catalyst for converting various derivatives of aldehyde to their corresponding amides. The current protocol can be useful criterion in the synthesis and stabilization of metal oxides and provides new insight in organic transformation.

A Molecular Iron-Based System for Divergent Bond Activation: Controlling the Reactivity of Aldehydes

The direct synthesis of amides and nitriles from readily available aldehyde precursors provides access to functional groups of major synthetic utility. To date, most reliable catalytic methods have typically been optimized to supply one product exclusively. Herein, we describe an approach centered on an operationally simple iron-based system that, depending on the reaction conditions, selectively addresses either the C=O or C-H bond of aldehydes. This way, two divergent reaction pathways can be opened to furnish both products in high yields and selectivities under mild reaction conditions. The catalyst system takes advantage of iron's dual reactivity capable of acting as (1) a Lewis acid and (2) a nitrene transfer platform to govern the aldehyde building block. The present transformation offers a rare control over the selectivity on the basis of the iron system's ionic nature. This approach expands the repertoire of protocols for amide and nitrile synthesis and shows that fine adjustments of the catalyst system's molecular environment can supply control over bond activation processes, thus providing easy access to various products from primary building blocks.

Product selectivity controlled by manganese oxide crystals in catalytic ammoxidation

The performances of heterogeneous catalysts can be effectively tuned by changing the catalyst structures. Here we report a controllable nitrile synthesis from alcohol ammoxidation, where the nitrile hydration side reaction could be efficiently prevented by changing the manganese oxide catalysts. α-Mn2O3 based catalysts are highly selective for nitrile synthesis, but MnO2-based catalysts including α, β, γ, and δ phases favour the amide production from tandem ammoxidation and hydration steps. Multiple structural, kinetic, and spectroscopic investigations reveal that water decomposition is hindered on α-Mn2O3, thus to switch off the nitrile hydration. In addition, the selectivity-control feature of manganese oxide catalysts is mainly related to their crystalline nature rather than oxide morphology, although the morphological issue is usually regarded as a crucial factor in many reactions.

Method for preparing amide compounds by using supported metal oxide catalytic material

The invention relates to a catalyst for preparing amide compounds, and aims to provide a method for preparing amide compounds by using a supported metal oxide catalytic material. The method comprisesthe following steps: uniformly mixing a solvent, water, an organic nitrile compound and the catalytic material; performing a reaction at 50-180 DEG C for 0.5-48 h; and hydrating and converting the organic nitrile compound into the corresponding amide compounds through the catalytic hydration effect of the catalyst in the reaction process. Adsorption and activation of the catalytic material to water molecules can be effectively regulated by regulating metal components loaded on the catalytic material and a catalytic material carrier, so that important amide compounds in chemical and agricultural processes are efficiently prepared. The provided method for preparing the amide compounds is effect, and has the advantages of high atom utilization rate in the reaction process, low reaction temperature, no additional reaction assistant in the synthesis process, no generation of toxic or harmful byproducts after the reaction, and green and environment-friendly synthesis process.

Method for preparing amide compounds by catalyzing organic nitrile hydration with oxide material

The invention relates to a catalyst for preparing amide compounds, and aims to provide a method for preparing amide compounds by catalyzing organic nitrile hydration with an oxide material. The methodcomprises the following steps: adding a solvent, an organic nitrile substrate, water and a catalyst into a sealable reaction container, and uniformly mixing; performing a reaction at 50-180 DEG C for0.5-24 h; and catalyzing hydration in the reaction process to make the nitrile compounds finally hydrated and converted into corresponding amide compounds. The catalyst is cheap and easy to obtain, and no precious metal is used, so that the preparation cost of the catalyst is low, and large-scale production of the catalyst is facilitated. In the reaction process, the atom utilization rate is high, the reaction temperature is low, no additional reaction assistant is needed in the synthesis process, no toxic or harmful byproduct is generated after the reaction, and the whole synthesis process is green and environmentally friendly.

Base-Mediated Amination of Alcohols Using Amidines

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcohols have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcohols are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands.

Transamidation for the Synthesis of Primary Amides at Room Temperature

Various primary amides have been synthesized using the transamidation of various tertiary amides under metal-free and mild reaction conditions. When (NH4)2CO3 reacts with a tertiary amide bearing an N-electron-withdrawing substituent, such as sulfonyl and diacyl, in DMSO at 25 °C, the desired primary amide product is formed in good yield with good funcctional group tolerance. In addition, N-tosylated lactam derivatives afforded their corresponding N-tosylamido alkyl amide products via a ring opening reaction.

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH3surrogates

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd?PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH3source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd?PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd?PS catalyst was easy to separate and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodology to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches.

Activation of nitriles by silver(I) N-heterocyclic carbenes: An efficient on-water synthesis of primary amides

A first example of silver(I) N-heterocyclic carbene (Ag(I)-NHC) catalyzed on-water synthesis of primary amides by hydration of nitriles under mild reaction conditions is described. This organometallic catalytic system has excellent tolerance for various homo-aromatic, hetero-aromatic and aliphatic nitriles to afford primary amides in good yields in neat water.