26367-48-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Chlorocarbonylacrylic acid ethyl ester is used as a key intermediate in the synthesis of various pharmaceuticals. Its role in the production process is crucial for creating a range of medications that can address different health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Chlorocarbonylacrylic acid ethyl ester is employed as an essential component in the formulation of different agrochemicals. Its presence in these products contributes to their effectiveness in agricultural applications, such as pest control and crop protection.
Used in Medicinal Chemistry:
3-Chlorocarbonylacrylic acid ethyl ester is used as a valuable reagent in the field of medicinal chemistry. Its properties allow researchers to explore new avenues in drug discovery and development, potentially leading to the creation of novel therapeutic agents.
Used in Synthetic Organic Chemistry:
3-Chlorocarbonylacrylic acid ethyl ester is also utilized as a reagent in synthetic organic chemistry, where it aids in the synthesis of complex organic molecules. Its versatility in this field makes it an indispensable tool for chemists working on the development of new chemical entities.

InChI:InChI=1/C6H7ClO3/c1-2-10-6(9)4-3-5(7)8/h3-4H,2H2,1H3/b4-3+

Upstream product

• 64-17-5 ethanol 
• 627-63-4 fumaryl dichloride 
• 2459-05-4 (E)-4-ethoxy-4-oxobut-2-enoic acid 
• 108-31-6 maleic anhydride 
• 2459-05-4 malonic acid monoethyl ester 
• 79-37-8 oxalyl dichloride 
• 623-91-6 diethyl Fumarate 

Downstream Products

• 124502-90-5 (E)-3-(2-Oxazol-2-yl-phenylcarbamoyl)-acrylic acid ethyl ester 
• 82313-27-7 exo-6-(Chlorcarbonyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-endo-5-carbonsaeure-ethylester 
• 82313-28-8 endo-5-(Chlorcarbonyl)-3-oxo-2-oxabicyclo<2.2.2>oct-7-en-exo-6-carbonsaeure-ethylester 
• 82669-49-6 (7-Chloro-1-isopropyl-2-oxo-5,5-diphenyl-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl)-acetic acid ethyl ester 
• 82669-51-0 (1-Benzyl-2-oxo-5,5-diphenyl-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl)-acetic acid ethyl ester 
• 106898-92-4 (E)-3-(Benzyl-{4-chloro-2-[(2-chloro-phenyl)-hydroxy-methyl]-phenyl}-carbamoyl)-acrylic acid ethyl ester 
• 82669-50-9 (1-Benzyl-7-chloro-2-oxo-5,5-diphenyl-1,2,3,5-tetrahydro-benzo[e][1,4]oxazepin-3-yl)-acetic acid ethyl ester 
• 88549-81-9 Benzoic acid (Z)-(1R,2R)-2-((E)-3-ethoxycarbonyl-acryloylamino)-1-methyl-hexa-3,5-dienyl ester 
• 106201-15-4 ethyl 3-<(2-hydroxyphenyl)carbamoyl>acrylate 
• 139115-70-1 ethyl (E)-4--4-oxobut-2-enoate 
• 106201-16-5 (Z)-3-[Benzyl-(2-hydroxy-phenyl)-carbamoyl]-acrylic acid ethyl ester 
• 10080-68-9 (E)-ethyl 4-hydroxybut-2-enoate 
• 203917-27-5 (E)-3-(2-Hydroxymethyl-6-methyl-phenylcarbamoyl)-acrylic acid ethyl ester 
• 203917-28-6 (E)-3-(2-Hydroxymethyl-3-methyl-phenylcarbamoyl)-acrylic acid ethyl ester 

Relevant academic research and scientific papers

[3+2] Cycloaddition of o-nitrophenyl azide to 3a,6-epoxyisoindoles

[3+2] Cycloaddition of o-nitrophenyl azide to the multiple bond of oxabicyclo[2.2.1]heptene moiety in substituted 3a,6-epoxyisoindoles was performed. The 1,3-dipolar addition reaction proceeded stereoselectively, producing a pair of isomeric cis-4,8a-epox

Chloroquine fumardiamides as novel quorum sensing inhibitors

Quorum sensing inhibitors (QSIs) that specifically interfere with bacterial cell-to-cell communication are considered as an alternative approach to conventional antibacterial therapy. In our study, a set of twenty-six fumardiamides with a quinoline head-group were evaluated as potential QSIs. Two strains of Gram-negative Chromobacterium violaceum (violacein-producing strain ATCC31532 and violacein-negative, mini-Tn5 mutant derivative CV026) were used as QS reporters for testing anti-QS and bactericidal activity of various quinoline fumardiamides. The initial screening of eighteen fumardiamides with primaquine, mefloquine and chloroquine scaffolds identified chloroquine derivatives as the most promising QSIs. Tail-group optimization of chloroquine fumardiamides led to the most active compounds 27, 29 and 30 bearing aminoethyl or piperidine moieties. At 400 μM concentration, these compounds inhibited the QS of C. violaceum strains in a manner similar to quercetin (the model QSI), while at the 40 μM concentration their inhibitory effect was twice less than that of quercetin. As none of the compounds displayed a bactericidal effect and that the QS inhibition was specific to the CV026 strain, our findings indicate that the structurally optimized chloroquine derivatives could function as quorum quenching (QQ) agents with a potential to block the signaling without entering the cell. In conclusion, our finding provides an important step toward the further design of agents targeting cell-to-cell communication.

Primaquine and chloroquine fumardiamides as promising antiplasmodial agents

This paper describes a continuation of our efforts in the pursuit of novel antiplasmodial agents with optimized properties. Following our previous discovery of biologically potent asymmetric primaquine (PQ) and halogenaniline fumardiamides (1–6), we now report their significant in vitro activity against the hepatic stages of Plasmodium parasites. Furthermore, we successfully prepared chloroquine (CQ) analogue derivatives (11–16) and evaluated their activity against both the hepatic and erythrocytic stages of Plasmodium. Our results have shown that PQ fumardiamides (1–6) exert both higher activity against P. berghei hepatic stages and lower toxicity against human hepatoma cells than the parent drug and CQ derivatives (11–16). The favourable cytotoxicity profile of the most active compounds, 5 and 6, was corroborated by assays performed on human cells (human breast adenocarcinoma (MCF-7) and non-tumour embryonic kidney cells (HEK293T)), even when glucose-6-phosphate dehydrogenase (G6PD) was inhibited. The activity of CQ fumardiamides on P. falciparum erythrocytic stages was higher than that of PQ derivatives, comparable to CQ against CQ-resistant strain PfDd2, but lower than CQ when tested on the CQ-sensitive strain Pf3D7. In addition, both sets of compounds showed favourable drug-like properties. Hence, quinoline fumardiamides could serve as a starting point towards the development of safer and more effective antiplasmodial agents.

Modulation of reactivities of dienophiles for diels-alder reactions via complexation of α,β-unsaturated chelating amides

We describe the modulation of reactivities of dienophiles for Diels-Alder reactions via a new principle based on chelating amides positioned adjacent to their C-C bond. It is demonstrated for modified acrylic acid derivatives and related dienophiles with three different chelating entities. Complexation of the chelators leads to an intensified electron-withdrawing effect leading to an enhancement of reactivity in Diels-Alder reactions depending on the complexed metal ion. The application of this new approach might be extended to other reactions with reacting entities adjacent to chelating amides.

SAHAquines, Novel Hybrids Based on SAHA and Primaquine Motifs, as Potential Cytostatic and Antiplasmodial Agents

We report the synthesis of SAHAquines and related primaquine (PQ) derivatives. SAHAquines are novel hybrid compounds that combine moieties of suberoylanilide hydroxamic acid (SAHA), an anticancer agent with weak antiplasmodial activity, and PQ, an antimalarial drug with low antiproliferative activity. The preparation of SAHAquines is simple, cheap, and high yielding. It includes the following steps: coupling reaction between primaquine and a dicarboxylic acid monoester, hydrolysis, a new coupling reaction with O-protected hydroxylamine, and deprotection. SAHAquines 5 a–d showed significant reduction in cell viability. Among the three human cancer cell lines (U2OS, HepG2, and MCF-7), the most responsive were the MCF-7 cells. The antibodies against acetylated histone H3K9/H3K14 in MCF-7 cells revealed a significant enhancement following treatment with N-hydroxy-N′-{4-[(6-methoxyquinolin-8-yl)amino]pentyl}pentanediamide (5 b). Ethyl (2E)-3-({4-[(6-methoxyquinolin-8-yl)amino]pentyl}carbamoyl)prop-2-enoate (2 b) and SAHAquines were the most active compounds against both the hepatic and erythrocytic stages of Plasmodium parasites, some of them at sub-micromolar concentrations. The results of our research suggest that SAHAquines are promising leads for new anticancer and antimalarial agents.

Discovery of Inhibitors of the Lipopolysaccharide Transporter MsbA: From a Screening Hit to Potent Wild-Type Gram-Negative Activity

The dramatic increase in the prevalence of multi-drug resistant Gram-negative bacterial infections and the simultaneous lack of new classes of antibiotics is projected to result in approximately 10 million deaths per year by 2050. We report on efforts to target the Gram-negative ATP-binding cassette (ABC) transporter MsbA, an essential inner membrane protein that transports lipopolysaccharide from the inner leaflet to the periplasmic face of the inner membrane. We demonstrate the improvement of a high throughput screening hit into compounds with on-target single digit micromolar (μM) minimum inhibitory concentrations against wild-type uropathogenic Escherichia coli, Klebsiella pneumoniae, and Enterobacter cloacae. A 2.98 ? resolution X-ray crystal structure of MsbA complexed with an inhibitor revealed a novel mechanism for inhibition of an ABC transporter. The identification of a fully encapsulated membrane binding site in Gram-negative bacteria led to unique physicochemical property requirements for wild-type activity.

Enantioselective Synthesis of N-Alkylamines through β-Amino C-H Functionalization Promoted by Cooperative Actions of B(C6F5)3and a Chiral Lewis Acid Co-Catalyst

We disclose a catalytic method for β-C(sp3)-H functionalization of N-alkylamines for the synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C6F5)3, and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C-H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described.

Artificial intelligence-designed stereoselective one-pot synthesis of trans-β-lactams and its application to cholesterol absorption inhibitor SCH 47949 synthesis

Cholesterol absorption inhibitor drug SCH 47949 is synthesized stereoselectively using an artificial intelligence design proposed by SYNSUP. The key step involves a stereoselective one-pot preparation of the trans-β-lactam system through thermal electrocyclization. The trans-β-lactam intermediate is converted to SCH 47949 by a series of functional group transformations proposed by SYNSUP.

Artificial intelligence designed drug synthesis: One-pot preparation of trans β-lactams and application to cholesterol absorption inhibitor SCH 47949 synthesis

An artificial intelligence designed SCH 47949 synthesis is achieved in a stereoselective manner. The key step contains a stereoselective one-pot construction of the trans β-lactam framework via thermal electrocyclization. N-arylation of the β-lactam ring system and a series of functional group transformations synthesized SCH 47949 in a reasonable chemical yield.

PRODRUGS OF KETAMINE, COMPOSITIONS AND USES THEREOF

Provided are prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine,composition and uses thereof. Compounds having formula (Ia) or (Ib) as the prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine, and pharmaceutical compositions comprising the compounds provided herein are used for treating or preventing a CNS disease.More particularly, the related diseases include depression and pain. (Ia) (Ib)