582-33-2

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 3-aminobenzoate is used as an anesthetic for fish, particularly in the form of its methanesulfonate salt. This application is beneficial for the proper handling and transportation of fish, as it helps to reduce stress and prevent injury during the process.
Used in Chemical Industry:
As a clear yellow to light brown liquid with a low melting point, Ethyl 3-aminobenzoate can be utilized in the chemical industry for various purposes, such as a starting material for the synthesis of other compounds or as an intermediate in the production of pharmaceuticals and other chemical products.
Used in Research and Development:
Due to its unique chemical properties, Ethyl 3-aminobenzoate can be employed in research and development for the study of its potential applications in various fields, including pharmaceuticals, materials science, and environmental science.

InChI:InChI=1/C9H11NO2.ClH/c1-2-12-9(11)7-4-3-5-8(10)6-7;/h3-6H,2,10H2,1H3;1H

Upstream product

• 618-98-4 ethyl 3-nitrobenzoate 
• 64-17-5 ethanol 
• 99-05-8 meta-aminobenzoic acid 
• 5100-22-1 ethyl 3-[(ethoxycarbonyl)amino]benzoate 
• 62-53-3 aniline 
• 93-89-0 benzoic acid ethyl ester 
• 7647-01-0 hydrogenchloride 
• 587-48-4 3-acetylaminobenzoic acid 
• 7664-41-7 ammonia 
• 58465-46-6 N-oxalyl-3-aminobenzoic acid 
• 56423-50-8 3-azido benzoic acid ethyl ester 
• 1045771-48-9 3-[2-(trimethylsilanyl)ethanesulfonylamino]benzoic acid ethyl ester 
• 24398-88-7 ethyl 3-bromobenzoate 
• 138-59-0 shikimic acid 

Downstream Products

• 3137-84-6 3-ethoxycarbonylphenyl isothiocyanate 
• 86253-07-8 3,3'-thioureylene-di-benzoic acid diethyl ester 
• 20967-87-7 3-[(aminothioxomethyl)amino]benzoic acid ethyl ester 
• 2463-16-3 ethyl 3-cyanobenzoate 
• 118719-00-9 ethyl 3-nitrosobenzoate 
• 14062-34-1 3-aminobenzohydrazide 
• 53084-60-9 ethyl 3-aminocyclohexanecarboxylate 
• 19305-32-9 3-acetylaminobenzoic acid ethyl ester 

Relevant academic research and scientific papers

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Synthesis and biological evaluation of 2,5-diaryl-1,3,4-oxadiazole derivatives as novel Src homology 2 domain-containing protein tyrosine phosphatase 2 (SHP2) inhibitors

The Src homology-2 domain containing-protein tyrosine phosphatase-2 (SHP2) is a convergent node for oncogenic cell-signaling cascades including the PD-L1/PD-1 pathway. As an oncoprotein as well as a potential immunomodulator, SHP2 has now emerged as an attractive target for novel anti-cancer agents. Although significant progress has been made in identifying chemotypes of SHP2 inhibitors, these specific compounds might not be clinically useful to inhibit frequently encountered mutated SHP2 variants. Consequently, it is highly desirable to develop chemically different SHP2 inhibitors sensitive to SHP2 mutants. This work developed a new type of SHP2 inhibitors with 2,5-diaryl-1,3,4-oxadiazole scaffold. The representative compound 6l exhibited SHP2 inhibitory activity with IC50 of 2.73 ± 0.20 μM, showed about 1.56-fold, 5.26-fold, and 7.36-fold selectivity for SHP2 over SHP1, PTP1B and TCPTP respectively. Further investigations confirmed that 6l behaved as mixed-type inhibitor sensitive to leukemia cell TF-1 and inhibited SHP2 mediated cell signaling and proliferation. Molecular dynamics simulation provided more detailed information on the binding modes of compounds and SHP2 protein. These preliminary results could provide a possible opportunity for the development of novel SHP2 inhibitors sensitive to SHP2 mutants with optimal potency and improved pharmacological properties.

The discovery of novel small molecule allosteric activators of aldehyde dehydrogenase 2

Aldehyde dehydrogenase 2 (ALDH2) plays important role in ethanol metabolism, and also serves as an important shield from the damage occurring under oxidative stress. A special inactive variant was found carried by 35–45% of East Asians. The variant carriers have recently been found at the higher risk for the diseases related to the damage occurring under oxidative stress, such as cardiovascular and cerebrovascular diseases. As a result, ALDH2 activators may potentially serve as a new class of therapeutics. Herein, N-benzylanilines were found as novel allosteric activators of ALDH2 by computational virtual screening using ligand-based and structure-based screening parallel screening strategy. Then a structural optimization was performed and has led to the discovery of the compound C6. It has good activity in vitro and in vivo, which could reduce infarct size by ～70% in ischemic stroke rat models. This study provided good lead compounds for the further development of ALDH2 activators.

Half-Sandwich Ruthenium Complexes of Amide-Phosphine Based Ligands: H-Bonding Cavity Assisted Binding and Reduction of Nitro-substrates

We present synthesis and characterization of two half-sandwich Ru(II) complexes supported with amide-phosphine based ligands. These complexes presented a pyridine-2,6-dicarboxamide based pincer cavity, decorated with hydrogen bonds, that participated in the binding of nitro-substrates closer to the Ru(II) centers, which is further supported with binding and docking studies. These ruthenium complexes functioned as the noteworthy catalysts for the borohydride mediated reduction of assorted nitro-substrates. Mechanistic studies not only confirmed the intermediacy of [Ru-H] in the reduction but also asserted the involvement of several organic intermediates during the course of the catalysis. A similar Ru(II) complex that lacked pyridine-2,6-dicarboxamide based pincer cavity substantiated its unique role both in the substrate binding and the subsequent catalysis.

Production process of ethyl m-aminobenzoate

The invention provides a production process of ethyl m-aminobenzoate, and the production process comprises the following steps: filling a trickle bed reactor with a catalyst DCyPP.Pd(OAc)2 and potassium carbonate, adding a mixture of 3-chloroaniline and ethanol, introducing carbon monoxide, keeping the pressure in the reactor at 0.1-0.2 MPa, carrying out carbonylation esterification reaction, and performing purifying by a rectifying tower to obtain the ethyl m-aminobenzoate with the molar yield of 97%, wherein the purity of the ethyl m-aminobenzoate is more than 98.5%. According to the method, ethyl m-aminobenzoate can be continuously produced, reaction raw materials are convenient and easy to obtain, the process is simple, reaction conditions are mild, reaction energy consumption is low, no waste acid is generated in the reaction process, and the method is suitable for large-scale production.

Biological Characterization, Mechanistic Investigation and Structure-Activity Relationships of Chemically Stable TLR2 Antagonists

Toll-like receptors (TLRs) build the first barrier in the innate immune response and therefore represent promising targets for the modulation of inflammatory processes. Recently, the pyrogallol-containing TLR2 antagonists CU-CPT22 and MMG-11 were reported; however, their 1,2,3-triphenol motif renders them highly susceptible to oxidation and excludes them from use in extended experiments under aerobic conditions. Therefore, we have developed a set of novel TLR2 antagonists (1–9) based on the systematic variation of substructures, linker elements, and the hydrogen-bonding pattern of the pyrogallol precursors by using chemically robust building blocks. The novel series of chemically stable and synthetically accessible TLR2 antagonists (1–9) was pharmacologically characterized, and the potential binding modes of the active compounds were evaluated structurally. Our results provide new insights into structure-activity relationships and allow rationalization of structural binding characteristics. Moreover, they support the hypothesis that this class of TLR ligands bind solely to TLR2 and do not directly interact with TLR1 or TLR6 of the functional heterodimer. The most active compound from this series (6), is chemically stable, nontoxic, TLR2-selective, and shows a similar activity with regard to the pyrogallol starting points, thus indicating the variability of the hydrogen bonding pattern.

Selective Optimization of Pranlukast to Farnesoid X Receptor Modulators

Selective optimization of side activities (SOSA) offers an alternative entry to early drug discovery and may provide rapid access to bioactive new chemical entities with desirable properties. SOSA aims to reverse a drug's side activities through structural modification and to design out the drug's original main action. We identified a moderate side activity for the cysteinyl leukotriene receptor 1 (CysLT1R) antagonist pranlukast on the farnesoid X receptor (FXR). Systematic structural modification of the drug allowed remarkable optimization of its partial FXR agonism to sub-nanonmolar potency. The resulting FXR modulators lack any activity on CysLT1R and are characterized by high selectivity, high metabolic stability, and low toxicity. With their favorable in vitro profile, these SOSA-derived FXR modulators constitute a new FXR ligand chemotype that appears suitable for further preclinical evaluation.

N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.

Improving the Potency of Cancer Immunotherapy by Dual Targeting of IDO1 and DNA

Herein we report the first exploration of a dual-targeting drug design strategy to improve the efficacy of small-molecule cancer immunotherapy. New hybrids of indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors and DNA alkylating nitrogen mustards that respectively target IDO1 and DNA were rationally designed. As the first-in-class examples of such molecules, they were found to exhibit significantly enhanced anticancer activity in vitro and in vivo with low toxicity. This proof-of-concept study has established a critical step toward the development of a novel and effective immunotherapy for the treatment of cancers.

AMINATION AND HYDROXYLATION OF ARYLMETAL COMPOUNDS

In one aspect, the present disclosure provides methods of preparing a primary or secondary amine and hydroxylated aromatic compounds. In some embodiments, the aromatic compound may be unsubstituted, substituted, or contain one or more heteroatoms within the rings of the aromatic compound. The methods described herein may be carried out without the need for transition metal catalysts or harsh reaction conditions.