114393-97-4

Usage

Chemical Properties

Off-White Low Melting Solid

Uses

An intermediate of Pioglitazone (P471000).

InChI:InChI=1/C16H17NO2/c1-2-13-3-6-15(17-11-13)9-10-19-16-7-4-14(12-18)5-8-16/h3-8,11-12H,2,9-10H2,1H3

Upstream product

• 5223-06-3 5-ethyl-2-(2-hydroxyethyl)pyridine 
• 123-08-0 4-hydroxy-benzaldehyde 
• 144809-26-7 2-(5-ethyl-pyridin-2-yl)ethyl methanesulfonate 
• 144809-27-8 toluene-4-sulfonic acid 2-(5-ethylpyridin-2-yl)ethyl ester 
• 1122-91-4 4-bromo-benzaldehyde 
• 87199-17-5 4-formylphenylboronic acid, 
• 23616-79-7 benzyltri(n-butyl)ammonium chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 58765-11-0 4-hydroxybenzaldehyde potassium salt 
• 1194-02-1 4-fluorobenzonitrile 
• 136402-00-1 4-[2-(5-ethylpyridin-2-yl)ethoxy] benzonitrile 

Downstream Products

• 1026443-02-6 Nicotinic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 1025798-31-5 Isonicotinic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 1026070-99-4 2-Methyl-benzoic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 1026276-66-3 Benzoic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 1027538-71-1 4-Nitro-benzoic acid [1-{4-[2-(5-ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 312690-32-7 2-[1-{4-[2-(5-Ethyl-pyridin-2-yl)-ethoxy]-phenyl}-meth-(E)-ylidene]-4-(3aR,7aS)-octahydro-isoindol-2-yl-4-oxo-butyric acid ethyl ester 
• 144809-28-9 5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione 
• 136401-69-9 5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione 
• 1207961-01-0 C₃₉H₃₄ClN₇O₂ 
• 1207961-05-4 C₃₉H₃₃F₂N₇O₂ 
• 1207961-07-6 2-(4'-chlorophenylamino)-4-(4'-fluorophenylamino)-6-[4'-{3''-(4'''-{2'-(5'-ethylpyridin-2'-yl)-ethoxy}-phenyl)-2''-propenon-1''-yl}-phenylamino]-s-triazine 

Relevant academic research and scientific papers

Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

Abstract: The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure–activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-γ (PPARγ) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-γ (PPARγ) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor. Graphical abstract: [Figure not available: see fulltext.].

Base Mediated Synthesis of Alkyl-aryl Ethers from the Reaction of Aliphatic Alcohols and Unsymmetric Diaryliodonium Salts

The base mediated coupling of aliphatic alcohol pronucleophiles with unsymmetric diaryliodonium salt electrophiles is described. This metal-free reaction is operationally simple, proceeds at mild temperature, and displays broad substrate scope to generate industrially important alkyl-aryl ethers in moderate to excellent yield. The synthetic utility of these reactions is demonstrated, and aspects of sustainability are highlighted by the use of unsymmetric aryl(mesityl)iodonium arylating reagents.

Synthesis and in vitro antimicrobial screening of new azetidin-2-ones of 5-ethyl pyridine-2-ethanol

A new series of azetidinones is described in this paper; Schiff base (4a-o) were synthesized from 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde, which was used to synthesize azetidinones (5a-o), (6a-o), and (7a-o). The structures of the synthesized compou

Phosphoryl chloride mediated synthesis of 5-arylidene-2,4- thiazolidinediones derivatives via aromatic bisulfite adducts

The carbon-carbon bond formation by the condensation of bisulfite adduct of aromatic aldehydes with thiazolidine-2, 4-dione to furnish 5-arylidene-2,4- thiazolidinedione's has been investigated. This novel methodology was applied to convert substituted aryl bisulfite adducts to corresponding 5-arylidene-2,4-thiazolidinedione's with POCl3 in less-polar solvents such as toluene, chlorobenzene and o-xylene. 5-(4-methoxybenzylidene) thiazolidine-2,4-dione and 5-(4-ethoxybenzylidene)thiazolidine-2,4-dione were obtained in good yields.

Design and synthesis of new imidazolinone derivatives as potential antifungal agents

A new series of chalcones, pyrimidines, and imidazolinone is described; chalcones (4a-o) were prepared from the lead 4-[2-(5-ethylpyridin-2-yl)ethoxy] benzaldehyde. Pyrimidines (5a-o) were prepared from the reaction of chalcones and guanidine nitrate in a

An improved process for pioglitazone and its pharmaceutically acceptable salt

An improved process for pioglitazone (1) is described. The process features high-yielding transformations employing inexpensive reagents and recoverable solvents.

NOVEL PROCESS FOR THE SYNTHESIS OF PIOGLITAZONE AND ITS SALTS THEREOF

Present invention relates to an improved process for the preparation of thiazolidinedione derivatives. Further the invention provides the hydrogenation of acid addition salt of benzylidene compound with less reducing agent under low Hydrogen gas pressure to get substantially pure thiazolidinedione derivatives with improved yields.

Synthesis and?antimicrobial studies of?a?new series of?2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles

A series of novel 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}-5-substituted-1,3,4-oxadiazoles were synthesized by the oxidative cyclisation of hydrazones derived from 4-[2-(5-ethylpyridin-2-yl)ethoxy]benzaldehyde and aroylhydrazines using chloramine-T as oxidant. IR, NMR and elemental analysis characterized the newly synthesized compounds. The synthesized compounds were evaluated for their antimicrobial activity and were compared with standard drugs. The compounds demonstrated potent to weak antimicrobial activity. Out of the compounds studied, compounds 8c and 8d showed significant inhibition. Compounds 8b, 8f, 8k and 8e showed moderate activity. The minimum inhibitory concentration of the compounds was in the range of 8-26 μg ml-1 against bacteria and 8-24 μg ml-1 against fungi. The title compounds represent a novel class of potent antimicrobial agents.

PROCESS FOR THE SYNTHESIS OF PIOGLITAZONE HYDROGEN CHLORIDE

The invention relates to a process for the synthesis of pioglitazone hydrogen chloride - which is an antidiabetic drug - via novel intermediates by reacting 4-[2-(5-ethyl-2-pyridinyl)-ethoxy]-benzaldehyde salt of formula (II), wherein HX is: HCI, CF3COOH, C4H4O4, (COOH)2 with a base and then thiazolidine-2,4-dione, and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methylene]-2,4-thiazolidinedione base is treated with hydrochloric acid and the obtained 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl] methylene]-2,4-tiazolidinedione hydrogen chloride of formula(III) is hydrogenated in the presence of a catalyst. Further objects of the invention are the salts of general formula (II) and the benzylidene derivative of formula (III).