1702-14-3

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
Ethyl 2-methyl-6-phenylpyridine-3-carboxylate is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic and pesticidal properties.
Used in Organic Synthesis:
As a building block in organic synthesis, Ethyl 2-methyl-6-phenylpyridine-3-carboxylate is utilized for the preparation of complex organic molecules. Its versatility in chemical reactions makes it a valuable component in the development of new chemical entities.
Used in Biological Research:
Ethyl 2-methyl-6-phenylpyridine-3-carboxylate is used as a subject of study in biological research for its potential antimicrobial, antiviral, and anti-inflammatory activities. These properties make it a candidate for further investigation into treatments for various diseases and conditions.
Used in Enzyme and Receptor Inhibition Studies:
Ethyl 2-methyl-6-phenylpyridine-3-carboxylate is also used in studies focused on enzyme and receptor inhibition. Its interaction with specific biological targets could lead to the development of new drugs that modulate these targets for therapeutic benefit.

InChI:InChI=1/C15H15NO2/c1-3-18-15(17)13-9-10-14(16-11(13)2)12-7-5-4-6-8-12/h4-10H,3H2,1-2H3

Upstream product

• 15724-86-4 E-2-chlorovinyl phenyl ketone 
• 626-34-6 ethyl aminocrotonate 
• 15397-33-8 3-Oxo-3-phenylpropanal 
• 13125-52-5 3-benzoylacrylonitrile 
• 41867-20-3 ethyl (E)-3-aminobut-2-enoate 
• 182363-00-4 (Z)-3-[(2-Hydroxy-1,1-dimethyl-ethyl)-methyl-amino]-1-phenyl-propenone 
• 3623-15-2 phenyl propargyl ketone 
• 626-34-6 ethyl 3-aminobut-2-enoate 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 1131-80-2 (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one 
• 141-97-9 ethyl acetoacetate 
• 1201-93-0 1-phenyl-3-dimethylaminoprop-2-enone 
• 1224695-43-5 (2Z,4E)-2-amino-3-ethoxycarbonyl-6-phenylhexadien-6-one 
• 4452-12-4 1-phenyl-3-(piperidin-1-yl)prop-2-en-1-one 

Downstream Products

• 102024-17-9 2,7-diphenyl-7,8-dihydro-pyrano[4,3-b]pyridin-5-one 
• 102549-15-5 6-phenyl-2-trans-styryl-nicotinic acid ethyl ester 
• 102024-32-8 7-(2-hydroxy-phenyl)-2-phenyl-7,8-dihydro-pyrano[4,3-b]pyridin-5-one 
• 66416-49-7 2-Methyl-6-phenyl-3-nicotinic acid 
• 94285-80-0 2-methyl-N,6-diphenylnicotinamide 
• 94285-78-6 N-allyl-2-methyl-6-phenylnicotinamide 
• 94285-82-2 N-allyl-6-phenyl-2-styrylnicotinamide 
• 94285-84-4 6,N-Diphenyl-2-((E)-styryl)-nicotinamide 
• 111849-67-3 2-(α,β-dibromo-phenethyl)-6-phenyl-nicotinic acid ethyl ester 
• 52090-57-0 2-methyl-6-phenylpyridine-3-carbohydrazide 
• 1408420-47-2 (Z)-2-methyl-N'-(2-oxoindolin-3-ylidene)-6-phenylnicotinohydrazide 
• 1408420-50-7 (Z)-2-methyl-N'-(2-oxoindolin-5-chloro-3-ylidene)-6-phenylnicotinohydrazide 
• 1408420-54-1 (Z)-2-methyl-N'-(2-oxoindolin-5-bromo-3-ylidene)-6-phenylnicotinohydrazide 

Relevant academic research and scientific papers

An improved synthesis of pyridine-thiazole cores of thiopeptide antibiotics

(Figure Presented) The oxidation of 2-methylthiazoles to 2-formylthiazoles simplifies the implementation of the Bagley variant of the Bohlmann-Rahtz reaction as a key step in a concise new route to pyridine cores of thiopeptide antibiotics.

A simple continuous flow microwave reactor

A new simple procedure for microwave-assisted organic synthesis under continuous flow processing has been developed for use in a monomodal microwave synthesizer with direct temperature control using the instrument's in-built IR sensor. This design makes optimum use of the standing wave cavity to improve the energy efficiency of microwave-assisted flow reactions.

Development of novel isatin–nicotinohydrazide hybrids with potent activity against susceptible/resistant Mycobacterium tuberculosis and bronchitis causing–bacteria

Joining the global fight against Tuberculosis, the world's most deadly infectious disease, herein we present the design and synthesis of novel isatin-nicotinohydrazide hybrids (5a–m and 9a–c) as promising anti-tubercular and antibacterial agents. The anti-tubercular activity of the target hybrids was evaluated against drug-susceptible M. tuberculosis strain (ATCC 27294) where hybrids 5d, 5g and 5h were found to be as potent as INH with MIC = 0.24 μg/mL, also the activity was evaluated against Isoniazid/Streptomycin resistant M. tuberculosis (ATCC 35823) where compounds 5g and 5h showed excellent activity (MIC = 3.9 μg/mL). Moreover, the target hybrids were examined against six bronchitis causing-bacteria. Most derivatives exhibited excellent antibacterial activity. K. pneumonia emerged as the most sensitive strain with MIC range: 0.49–7.81 μg/mL. Furthermore, a molecular docking study has proposed DprE1 as a probable enzymatic target for herein reported isatin-nicotinohydrazide hybrids, and explored the binding interactions within the vicinity of DprE1 active site.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

Green synthesis method of nicotinic acid ester compounds based on non-metallic conditions

The invention discloses a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, and belongs to the technical field of organic synthesis. The method comprises the following steps of (III) replacing cyclopropanol and (II) substituted enamine ester as a raw material, taking tetramethyl piperidine nitrogen oxide as an oxidizing agent, 110 - 130 °C, stirring and reacting in an organic solvent to synthesize a (I) nicotinate compound. The invention provides a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, wherein cyclopropanols and enamine esters are taken as raw materials, and a polysubstituted nicotinate is synthesized through a strategy of oxidative dehydrogenation of ketene cyclization.

Synthesis method of pyridine-3-formate compound

The invention discloses a synthesis method of a pyridine-3-formate compound, and belongs to the technical field of organic synthesis. The synthesis method comprises the following step: using an aminoalkenoate compound and an alpha, beta-saturated ketone compound or an alpha, beta-saturated aldehyde compound as raw materials, and performing one-pot multi-step serial reaction under the action of acatalyst, a ligand and an oxidant to obtain the pyridine-3-formate compound. The synthesis method has the advantages of simple and convenient operation, mild conditions, wide application range of a substrate, and the like, and is suitable for industrial production.

Synthesis of Functionalized Pyridines via Cu(II)-Catalyzed One-Pot Cascade Reactions of Inactivated Saturated Ketones with Electron-Deficient Enamines

In this paper, a novel and efficient synthesis of 3-acylpyridines and pyridine-3-carboxylates through the oxidative one-pot sequential reactions of inactivated saturated ketones with electron-deficient enamines is presented. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through an oxidative dehydrogenation of the saturated ketone substrate, followed by its [3+3] annulation with β-enaminone or β-enaminoester via a cascade process, including Michael addition, aldol type condensation, and oxidative aromatization.

Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant

A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.

Consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz syntheses of tri- and tetrasubstituted pyridines

The concatenation of the modified Sonogashira alkynone synthesis and the Bagley-Bohlmann-Rahtz pyridine synthesis gives novel consecutive three- and four-component coupling-Bagley-Bohlmann-Rahtz (cBBR) syntheses of tri- and tetrasubstituted pyridines in a one-pot fashion. With these processes 15 differently substituted 3-ethoxycarbonyl 2-methylpyridines can be readily obtained in modest to moderate yields.

Protective effect of novel substituted nicotine hydrazide analogues against hypoxic brain injury in neonatal rats via inhibition of caspase

In hypoxic-ischemic injury of the brain of neonates, the level of caspase-3 was found to be aberrantly activated. Its overexpression leads to the alteration of cytoskeleton protein fodrin and loss of DNA repair enzyme which ultimately results in neurological impairment and disability. Concerning this, the present study was intended to develop novel nicotine hydrazide analogues as caspase inhibitors via efficient synthetic route. These compounds were subsequently tested for inhibitory activity against caspase-3 and -7 where they exhibit highly potent activity against caspase-3 revealing compound 5k as most potent inhibitor (IC50 = 19.4 ± 2.5 μM). In Western blot analysis, 5k considerably inhibits the overexpression of caspase-3. The aryl nicotinate of compound 5k, as indicated by molecular docking was found to engage His121 and critical enzyme thiols, i.e., Cys163 of caspase-3 for its potent activity. Moreover, histopathological examination of brain tissues and hippocampus neurons showed that compound 5k considerably improves the brain injury and exert neuroprotective effects in hypoxic-ischemic (HI). In brain homogenate, 5k significantly improves the activity of MDA, SOD, GSH-Px, CAT and T-AOC to exert its beneficial effect against oxidative stress induced by HI injury.