13214-64-7

Usage

Uses

Used in Pharmaceutical Industry:
(4-METHOXY-BENZOYLAMINO)-ACETIC ACID is used as a chemical intermediate for the synthesis of various drugs, contributing to the development of new therapeutic agents.
Used in Research and Development:
(4-METHOXY-BENZOYLAMINO)-ACETIC ACID is used as a building block in the creation of new chemical compounds, facilitating innovative research and the advancement of chemical science.
Used as an Enzyme Inhibitor:
(4-METHOXY-BENZOYLAMINO)-ACETIC ACID is used in biological research as a potential inhibitor of enzymes, providing insights into enzyme function and the development of enzyme-targeted therapies.
Used for Receptor Binding Studies:
(4-METHOXY-BENZOYLAMINO)-ACETIC ACID is used in studies involving the binding to specific receptors in the body, aiding in the understanding of receptor-ligand interactions and the design of receptor-targeted drugs.

InChI:InChI=1/C10H11NO4/c1-15-8-4-2-7(3-5-8)10(14)11-6-9(12)13/h2-5H,6H2,1H3,(H,11,14)(H,12,13)/p-1

Upstream product

• 186581-53-3 diazomethane 
• 2482-25-9 4-hydroxyhippuric acid 
• 36701-37-8 silver(I) glycinate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 56-40-6 glycine 
• 30364-57-9 4-methoxybenzoic acid 2,5-dioxo-1-pyrrolidinyl ester 
• 7464-46-2 p-nitrophenyl p-methoxybenzoate 
• 155164-68-4 4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one 
• 100-09-4 4-methoxybenzoic acid 
• 51220-57-6 ethyl 2-(4-methoxybenzamido)acetate 
• 67-56-1 methanol 
• 75152-19-1 2-(4-methoxy-phenyl)-4H-oxazol-5-one 

Downstream Products

• 39806-46-7 1-(4-methoxy-benzoyl)-2-thioxo-imidazolidin-4-one 
• 4211-92-1 2-(4-methoxy)phenyl-4-(thiophen-2-ylmethylene)-5-oxazolinone 
• 19747-06-9 4-(4-chloro-benzylidene)-2-(4-methoxy-phenyl)-4H-oxazol-5-one 
• 60776-68-3 2-(4-methoxy-phenyl)-oxazole-4,5-dione 4-p-tolylhydrazone 
• 60776-67-2 2-(4-methoxy-phenyl)-oxazole-4,5-dione 4-phenylhydrazone 
• 19747-07-0 4-isopropylidene-2-(4-methoxy-phenyl)-4H-oxazol-5-one 
• 54926-15-7 N-formyl-(4-methoxy)benzamide 
• 103369-11-5 N-(acetoxymethyl)-4-methoxybenzamide 
• 75152-16-8 (4-Methoxy-benzoylamino)-acetic acid 4-nitro-phenyl ester 
• 100-09-4 4-methoxybenzoic acid 
• 56-40-6 glycine 
• 91146-23-5 perchlorate de p-methoxyphenyl-2 oxazolonium 
• 3400-22-4 4-methoxy-N-methylbenzamide 
• 425380-61-6 (Z)-2-(4-methoxyphenyl)-4-(1-naphthylmethylene)-5(4H)-oxazolone 

Relevant academic research and scientific papers

Palladium-catalyzed ortho-arylation of benzoic acid derivatives via C-H bond activation using an aminoacetic acid bidentate directing group

A highly efficient protocol for the palladium-catalyzed ortho-arylation of benzoic acid derivatives by aryl iodides is described with an aminoacetic acid based N,O bidentate directing group. This protocol can be applied to various benzoyl aminoacetic acids and aryl iodides with both electron-donating and electron-withdrawing groups. Remarkably, the nature of a new directing group drives selective C-H bond activation to afford only monoarylation products in good to excellent yields.

Kinetics and Mechanisms of the Aminolysis of N-Hydroxysuccinimide Esters in Aqueous Buffers

Rate constants for the aminolysis of the N-hydroxysuccinimide (NHS) ester of p-methoxybenzoic acid, in aqueous buffer systems (20percent dioxane), have been determined under pseudo-first-order conditions.For the amines studied (pKa = 7.60-11.1), the data fit the rate expression kobsd - kOH--> = k1free.This rate equation is in contrast to the two-term rate equation (kobsd = k1 + k22) obtained for this reaction in anhydrous dioxane (Cline, G.W.; Hanna, S.B.J.Am.Chem.Soc 1987, 109, 3087) and is suggestive of a disproportionate decrease in the catalyzed vs the uncatalyzed reaction path upon changing from a nonaqueous to an aqueous solvent system.The correlation of amine basicity with the nucleophilic rate constant, k1, yields a slope βnuc = 1.0.The magnitude of βnuc, in terms of a reaction mechanism where a tetrahedral intermediate is formed in a fast preequilibrium followed by rate-determining breakdown to products, reflects the sensitivity to changes in charge accumulation in the formation of the tetrahedral intermediate.The resultant increased rate constants, with increased basicity, are due to the effect of an increased concentration of the tetrahedral intermediate.A qualitative evaluation of the literature and current data concerning the leaving ability of N-hydroxy esters, in comparison to phenyl esters (equivalent acyl groups and nucleophiles), reveals that, with leaving groups of comparable basicity, the nucleophilic rate constants for N-hydroxy esters are about 2 orders of magnitude greater than that for phenyl esters.

Anthranilate 4H-oxazol-5-ones: Novel small molecule antibacterial acyl carrier protein synthase (AcpS) inhibitors

D-optimal design and Projection to Latent Structures (PLS) analysis were used to optimize screening hit 5 (B. subtilis AcpS IC50: 15 μM, B. subtilis MIC: >200 μM) into a series of 4H-oxazol-5-one, small molecule, antibacterial, AcpS inhibitors. Specifically, 15, 16 and 18 show μM or sub-μM AcpS inhibition (IC50s: 15: 1.1 μM, 16: 1.5 μM, 18: 0.27 μM) and moderate antibacterial activity (MICs: 12.5-50 μM) against B. subtilis, E. faecalis ATCC, E. faecalis VRE and S. pneumo+.

Synthesis and Biological Evaluation of New Diarylpyrazole and Triarylimidazoline Derivatives as Selective COX-2 Inhibitors

New series of diarylpyrazoles 8a–f and triarylimidazoline-5-ones 11a–g were synthesized and evaluated for their in vitro cyclooxygenase-1 (COX-1) and COX-2 inhibitory activity and in vivo anti-inflammatory activity. The synthesized compounds showed good selectivity for COX-2; compounds 8a, 8d, 8f, 11a, and 11c exhibited the highest COX-2 selectivity indexes (SI = 4.77–5.43) compared to the reference drug celecoxib (SI = 7.8). All compounds showed good in vivo anti-inflammatory activity, especially compounds 8a, 8f, 11c, and 11d, which also showed some similarities to the time interval pattern of celecoxib at all different time intervals (1, 3, and 6 h).

Synthesis and evaluation of new phenyl acrylamide derivatives as potent non-nucleoside anti-HBV agents

As a continuation of our previous work, a series of new phenyl acrylamide derivatives (4Aa-g, 4Ba-t, 5 and 6a-c) were designed and synthesized as non-nucleoside anti-HBV agents. Among them, compound 4Bs could potently inhibit HBV DNA replication in wild-type and lamivudine (3TC)/entecavir resistant HBV mutant strains with IC50 values of 0.19 and 0.18 μM, respectively. Notably, the selective index value of 4Bs was above 526, indicating the favorable safety profile. Interestingly, unlike nucleoside analogue 3TC, 4Bs could significantly inhibit 3.5 kb pgRNA expression. Molecular docking study revealed that 4Bs could fit well into the dimer-dimer interface of HBV core protein by hydrophobic, π–π and H-bond interactions. Considering the potent anti-HBV activity, low toxicity and diverse anti-HBV mechanism from that of nucleoside anti-HBV agent 3TC, compound 4Bs might be a promising lead to develop novel non-nucleoside anti-HBV therapeutic agents, and warranted further investigation.

Synthesis, characterization and anticancer activity of (5,1-substituted)-3-(indoline-4-(thiophene- 2-yl-methylene)-2-(p-tolyl)-2-methylene)-4,3-dihydro-1h-imidazole-5-one derivatives

The synthesis of novel imidazole-5-one derivatives (5a-j) was allowed in a conventional method by way of Erlenmeyer and Schiff base mechanism. Compound 2a was synthesized by Erlenmeyer reaction of N-(4-methoxy benzoyl)glycine with 2-thiophene-carboxaldehyde in the presence of acetic anhydride and anhydrous sodium acetate. Finally, it undergoes dehydration reaction with Schiff bases of isatin derivatives (4a-j) to yield final compounds 5a-j. The organic potentials of the newly synthesized imidazole-5-one derivatives have been evaluated for their in vitro anticancer activity by MTT assay method. It against MCF-7 cells as comparison with doxorubicin popular drug. The synthesized compounds 5e, 5f and 5j exhibited excellent anticancer activity against MCF-7 cell lines.

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

Piperidine thiazole derivative containing bisamide structure as well as preparation method and application thereof

The invention discloses a piperidine thiazole derivative containing a bisamide structure, and also discloses a preparation method of the piperidine thiazole derivative and application of the piperidine thiazole derivative as a sterilization agent and an insecticide. The invention provides the novel piperidine thiazole derivative containing the bisamide structure; the preparation method is simpleand convenient; the piperidine thiazole derivative can be used for preventing and treating cucumber gray mold, rice sheath blight diseases and potato late blight diseases, has good sterilization activity, can be used for preventing and treating insect pest of armyworm, black bean aphid, tetranychus telarius linne and the like, and lays the foundation for the invention and development of piperidinethiazole pesticides.

Inhibition studies on a panel of human carbonic anhydrases with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with KIs spanning in the low micromolar range.

Design, Synthesis, and Evaluation of the Anticancer Properties of a Novel Series of Imidazolone Fused Pyrazolo[1,5-a]pyrimidine Derivatives

A novel series of imidazolone fused pyrazolo[1,5-a]pyrimidine derivatives has been designed and synthesized using a convergent approach, and the structures of these compounds were confirmed by 1H NMR, 13C NMR, ESI-MS, and IR analyses. These new compounds were tested for their in vitro antiproliferative activity using an 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Out of the 20 derivatives prepared in the current study, compounds 8h, 8n, and 8r exhibited good anticancer activities tested against HeLa cells and HepG2 cells. However, the in vitro anticancer activity of compound 8r against HeLa, HepG2, and MCF-7 cell lines is superior to the marketed drugs Paclitaxel and SAHA.