159153-39-6

Usage

Uses

Used in Chemical Synthesis:
3-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl ester is used as a chemical intermediate for the synthesis of various organic compounds. Its unique molecular structure, which includes a pyridine ring and an acrylate group, makes it a valuable building block in the creation of complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl ester is used as a starting material for the development of new drugs. Its structural features can be exploited to design molecules with potential therapeutic applications, such as in the treatment of various diseases.
Used in Material Science:
3-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl ester is used as a component in the development of new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with tailored characteristics, such as improved stability or enhanced reactivity.
Used in Research and Development:
In research and development settings, 3-(6-Chloro-pyridin-3-yl)-acrylic acid ethyl ester is used as a model compound to study the properties and reactivity of esters and other related compounds. This can provide valuable insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.

InChI:InChI=1/C10H10ClNO2/c1-2-14-10(13)6-4-8-3-5-9(11)12-7-8/h3-7H,2H2,1H3/b6-4+

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 23100-12-1 6-chloronicotinylaldehyde 
• 73781-91-6 6-Chloronicotinic acid methyl ester 
• 1530-45-6 (carbethoxymethyl)triphenylphosphonium bromide 
• 53939-30-3 5-bromo-2-chloropyridine 
• 140-88-5 ethyl acrylate 
• 21543-49-7 2-Chloro-5-hydroxymethylpyridine 
• 5326-23-8 6-Chloro-3-pyridinecarboxylic acid 
• 69045-79-0 2-choro-5-iodopyridine 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 876157-50-5 ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-3-pyridyl)acrylate 
• 876159-80-7 ethyl (2E)-3-(6-{[(3R)-1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-3-pyridyl)acrylate 

Relevant academic research and scientific papers

Design, synthesis, and characterization of α-ketoheterocycles that additionally target the cytosolic port Cys269 of fatty acid amide hydrolase

A series of α-ketooxazoles incorporating electrophiles at the C5 position of the pyridyl ring of 2 (OL-135) and related compounds were prepared and examined as inhibitors of fatty acid amide hydrolase (FAAH) that additionally target the cytosolic port Cys269. From this series, a subset of the candidate inhibitors exhibited time-dependent FAAH inhibition and noncompetitive irreversible inactivation of the enzyme, consistent with the targeted Cys269 covalent alkylation or addition, and maintained or enhanced the intrinsic selectivity for FAAH versus other serine hydrolases. A preliminary in vivo assessment demonstrates that these inhibitors raise endogenous brain levels of anandamide and other FAAH substrates upon intraperitoneal (i.p.) administration to mice, with peak levels achieved within 1.5-3 h, and that the elevations of the signaling lipids were maintained >6 h, indicating that the inhibitors effectively reach and remain active in the brain, inhibiting FAAH for a sustained period.

HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF

Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.

Dimethyl sulfoxide mediated elimination reactions in 3-aryl 2,3-dihalopropanoates: Scope and mechanistic insights

(Chemical Equation Presented) Dimethyl sulfoxide (DMSO) efficiently causes the reductive elimination of 3-aryl 2,3-dibromopropanoates to cinnamates with good yield. With 3-phenyl 2,3-dihalopropanoates, debromination is the major pathway providing 3-phenylacrylate derivatives in high yields, whereas dehydrobromination is a competing pathway with thiophene derivatives. 1H NMR, 81Br NMR, and MS techniques indicated the formation of brominated-DMSO, MeBr, and HBr as byproducts in this transformation with no evidence for the formation of Br2. The dual role of DMSO as a nucleophile and bromine scavenger accounts for the products formed in this reaction.

HYDROXYAMIDE COMPOUNDS HAVING ACTIVITY AS INHIBITORS OF HISTONE DEACETYLASE (HDAC)

A compound having the following formula (I): wherein R1 is hydrogen, lower alkyl, lower alkenyl, lower or higher alkynyl, cyclo(lower)alkyl, cyclo(higher)alkyl, cyclo(lower)alkyl(lower)alkyl, cyclo(higher)alkyl(lower)alkyl, cyclo(lower)alkenyl(

Ruthenium-Catalyzed Heck-Type Olefination and Suzuki Coupling Reactions: Studies on the Nature of Catalytic Species

Ruthenium-catalyzed Heck olefination and Suzuki cross coupling reactions have been developed. When starting with a ruthenium complex [RuCl 2(p-cymene)]2 as a homogeneous catalyst precursor, induction periods were observed and ruthenium colloids of zero oxidation state were generated under catalytic conditions. Isolated ruthenium colloids carried out the olefination, implying that active catalytic species are ruthenium nanoclusters. To support this hypothesis, ruthenium nanoparticles stabilized with dodecylamine were independently prepared via a hydride reduction procedure, and their catalytic activity was subsequently examined. Olefination of iodobenzene with ethyl acrylate was efficiently catalyzed by the ruthenium nanoparticles under the same conditions, which could be also reused for the next runs. In poisoning experiments, the conversion of the olefination was completely inhibited in the presence of mercury, thus supporting our assumption on the nature of catalytic species. No residual ruthenium was detected from the filtrate at the end of the reaction. On the basis of the postulation, a heterogeneous catalyst system of ruthenium supported on alumina was consequently developed for the Heck olefination and Suzuki cross coupling reactions for the first time. It turned out that substrate scope and selectivity were significantly improved with the external ligand-free catalyst even under milder reaction conditions when compared to results with the homogeneous precatalyst. It was also observed that the immobilized ruthenium catalyst was recovered and reused up to several runs with consistent efficiency. Especially in the Suzuki couplings, the reactions could be efficiently carried out with as low as 1 molpercent of the supported catalyst over a wide range of substrates and were scaled up to a few grams without any practical problems, giving coupled products with high purity by a simple workup procedure.

Synthesis and antifungal activities of R-102557 and related dioxane- triazole derivatives

Novel triazole compounds with a dioxane ring were synthesized. Condensation of the diol precursor 10 with various aromatic aldehydes 11 - 13 under acidic conditions afforded a series of dioxane-triazole compounds 14 - 16. The antifungal activities of the compounds 14 - 16 were evaluated in vivo in mice infection models against Candida and Aspergillus species. High activities were seen for the derivatives with one or two double bond(s) and an aromatic ring substituted with an electron-withdrawing group in the side chain. Among the derivatives, R-102557 (16R: Ar=4-(2,2,3,3- tetrafluoropropoxy)phenyl) showed excellent in vivo activities against Candida, Aspergillus and Cryptococcus species. It also showed high tolerance in a preliminary toxicity study in rats.

[3 + 2] Cycloaddition of nonstabilized azomethine ylides. 7. Stereoselective synthesis of epibatidine and analogues

Epibatidine (1) is synthesized by employing a [3 + 2] cycloaddition strategy as a key step via nonstabilized azomethine ylide 10, generated by one-electron oxidative double desilylation of N-benzyl-2,5- bis(trimethylsilyl)pyrrolidine (12). Cycloaddition of 10 with trans-ethyl-3- (6-chloro-3-pyridyl)-2-propenoate (22a) gives 26 in which the 6-chloro-3- pyridyl moiety is endo-oriented. Decarboxylation followed by debenzylation gives unnatural epimer 30 of 1. The required cycloadduct 33, in which 6- chloro-3-pyridyl moiety is exo-oriented, is obtained stereoselectively utilizing cis-ethyl-(6-chloro-3-pyridyl)-2-propenoate (22b) as dipolarophile. 30 is also converted to 1 by epimerization reaction using KO(t)Bu. An alternative route involving conjugate addition of 6-chloro-3-iodo pyridine (37) to 36, obtained by cycloaddition of 10 with ethyl propiolate, is also suggested for the stereoselective synthesis of 1. A number of substituted epibatidines (38, 39, 40, 41, and 42) are synthesized through this strategy using appropriate dipolarophiles. Formal synthesis of the N-methyl homoepibatidine 48 and its epimer 46 is suggested from the cycloaddition of homologous azomethine ylide 44, derived from 43, with 22a and 22b, respectively.

Therapeutic phenoxyalkylheterocycles

Compounds of the formula STR1 wherein Q is chosen from the group consisting of pyridyl, pyrazyl, pyrimidyl, quinolyl, indolyl and 7-azaindolyl or any of these substituted with one or two substituents; Y is an alkylene bridge of 3-9 carbon atoms; R1 and R2 are each independently chosen from hydrogen, halo, alkyl, alkenyl, amino, alkylthio, hydroxy, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkoxy, nitro, carboxy, alkoxycarbonyl, dialkylaminoalkyl, alkylaminoalkyl, aminoalkyl, difluoromethyl, trifluoromethyl or cyano; R3 is alkoxycarbonyl, alkyltetrazolyl, substituted or unsubstituted phenyl or heterocyclyl, the N-oxide thereof, or a pharmaceutically acceptable acid addition salt thereof is an effective antipicornaviral agent.