122320-74-5 Usage
Description
5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione, also known as (5E)-Rosiglitazone, is a chemical compound derived from the Rosiglitazone family. It is the E-isomer of Rosiglitazone (R693505) and possesses a unique chemical structure that allows it to interact with specific biological targets. 5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione is characterized by its ability to bind to peroxisome proliferator-activated receptor gamma (PPAR-γ), playing a crucial role in the regulation of cellular processes.
Uses
Used in Pharmaceutical Industry:
5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione is used as an insulin sensitizer for the treatment of type 2 diabetes. Its primary application is to enhance the sensitivity of the body's cells to insulin, thereby improving glucose uptake and reducing blood sugar levels. By binding to PPAR-γ, it modulates the expression of genes involved in glucose and lipid metabolism, contributing to better management of diabetes.
Used in Research and Development:
In the field of research and development, 5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione serves as a valuable compound for studying the mechanisms of insulin resistance and the role of PPAR-γ in glucose and lipid metabolism. It can be used to develop new drugs or therapies targeting PPAR-γ for various metabolic disorders, including obesity and dyslipidemia.
Used in Drug Delivery Systems:
Similar to gallotannin, 5-[4-[2-[N-Methyl-N-(2-pyridinyl)amino]ethoxy]benzylidene]-2,4-thiazolidinedione can also be incorporated into drug delivery systems to improve its bioavailability, targeting, and therapeutic outcomes. Researchers can explore the use of various organic and metallic nanoparticles as carriers for this compound, aiming to enhance its delivery and efficacy in treating type 2 diabetes and other related conditions.
Check Digit Verification of cas no
The CAS Registry Mumber 122320-74-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,2,3,2 and 0 respectively; the second part has 2 digits, 7 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 122320-74:
(8*1)+(7*2)+(6*2)+(5*3)+(4*2)+(3*0)+(2*7)+(1*4)=75
75 % 10 = 5
So 122320-74-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H17N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,12H,10-11H2,1H3,(H,20,22,23)/b15-12-
122320-74-5Relevant articles and documents
Preparation method of rosiglitazone
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, (2020/12/29)
The invention provides a preparation method of rosiglitazone. The preparation method is characterized by comprising the following steps: reacting 2-chloropyridine with 2-methylaminoethanol under the catalysis of sodium triphenylmethyl to generate 2-[N-methyl-N-(2-pyridine) amino] ethanol; then carrying out Williamson synthesis reaction on the 2-[N-methyl-N-(2-pyridine) amino] ethanol and 4-fluorobenzaldehyde under the catalysis of bis (trimethylsilyl) amino potassium to obtain 4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzaldehyde; then carrying out condensation reaction with thiazoline-2,4-diketone to obtain 5-{4-[2-[N-methyl-N-(2-pyridine) amino] ethoxy] benzylidene} thiazoline-2, 4-diketone; and carrying out reduction reaction under the catalysis of an organic manganese reagent to obtain the rosiglitazone. The preparation method is simple, mild in condition, high in reaction yield and suitable for industrial production.
Process for the Preparation of Intermediates of Rosiglitazone, Rosiglitazone and New Polymorphic Forms Thereof
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Page/Page column 4, (2009/09/28)
The invention relates to a polymorphic form of 5-(4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzylidene)-2,4-thiazolidinedione (Formula (I)): to a process for its preparation and to the use of such compound for preparing rosiglitazone in the form of a free base or a salt thereof. The invention also relates to a polymorphic form of rosiglitazone in the form of a free base, to a process for its preparation and to the use of such polymorph for preparing a salt of rosiglitazone. The invention also relates to a process of preparing a polymorphic form of a rosiglitazone salt.
COMPOUNDS
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, (2008/06/13)
Compounds of formula (I) or a tautomeric form thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable solvate thereof, wherein: A1 represents a substituted or unsubstituted aromatic heterocyclyl group; R1 represents a hydrogen atom, an alkyl group, an acyl group, an aralkyl group, wherein the aryl moiety may be substituted or unsubstituted, or a substituted or unsubstituted aryl group; R2 and R3 each represent hydrogen, or R2 and R3 together represent a bond; A2 represents a benzene ring having in total up to five substituents; and n represents an integer in the range of from 2 to 6; pharmaceutical compositions containing such compounds and the use of such compounds and compositions in medicine