![molecular formula C16H13F6N5O B8811113 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one](/img/structure/B8811113.png)
3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one
Overview
Description
3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one is a potent, orally active inhibitor of dipeptidyl peptidase IV (DPP-IV). This compound has shown significant potential in the treatment of type 2 diabetes due to its ability to improve glucose tolerance .
Preparation Methods
Synthetic Routes and Reaction Conditions
The synthesis of this compound involves the incorporation of fused heterocycles, specifically triazolopiperazinesThe reaction conditions often involve the use of strong bases and solvents like dimethyl sulfoxide (DMSO) to facilitate the formation of the desired product .
Industrial Production Methods
Industrial production of this compound follows similar synthetic routes but on a larger scale. The process is optimized for higher yields and purity, often involving multiple purification steps such as recrystallization and chromatography to ensure the final product meets pharmaceutical standards .
Chemical Reactions Analysis
Types of Reactions
This compound undergoes various chemical reactions, including:
Oxidation: The compound can be oxidized to form different derivatives.
Reduction: Reduction reactions can modify the functional groups, leading to different analogs.
Common Reagents and Conditions
Common reagents used in these reactions include oxidizing agents like potassium permanganate, reducing agents like lithium aluminum hydride, and various nucleophiles for substitution reactions. The conditions often involve controlled temperatures and inert atmospheres to prevent unwanted side reactions .
Major Products
The major products formed from these reactions are typically analogs of the original compound with modified functional groups, which are then tested for their biological activities .
Scientific Research Applications
This compound has a wide range of scientific research applications:
Chemistry: It is used as a model compound to study the effects of trifluoromethyl and trifluorophenyl groups on biological activity.
Biology: The compound is used to investigate the role of DPP-IV in glucose metabolism and its potential as a therapeutic target.
Medicine: It has shown promise in the treatment of type 2 diabetes by improving glucose tolerance and insulin sensitivity.
Mechanism of Action
The compound exerts its effects by inhibiting dipeptidyl peptidase IV (DPP-IV), an enzyme involved in the degradation of incretin hormones. By inhibiting DPP-IV, the compound increases the levels of active incretin hormones, which in turn enhance insulin secretion and decrease glucagon release, leading to improved glucose homeostasis .
Comparison with Similar Compounds
Similar Compounds
Sitagliptin: Another DPP-IV inhibitor with a similar mechanism of action but different chemical structure.
Vildagliptin: Also a DPP-IV inhibitor, but with different pharmacokinetic properties.
Saxagliptin: Another compound in the same class, with variations in its chemical structure and biological activity.
Uniqueness
What sets 3-Amino-1-(3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one apart is its unique combination of trifluoromethyl and trifluorophenyl groups, which contribute to its high potency and selectivity as a DPP-IV inhibitor. This makes it a valuable compound for further research and development in the field of metabolic disorders .
Properties
Molecular Formula |
C16H13F6N5O |
|---|---|
Molecular Weight |
405.30 g/mol |
IUPAC Name |
3-amino-1-[3-(trifluoromethyl)-6,8-dihydro-5H-[1,2,4]triazolo[4,3-a]pyrazin-7-yl]-4-(2,4,5-trifluorophenyl)but-2-en-1-one |
InChI |
InChI=1S/C16H13F6N5O/c17-10-6-12(19)11(18)4-8(10)3-9(23)5-14(28)26-1-2-27-13(7-26)24-25-15(27)16(20,21)22/h4-6H,1-3,7,23H2 |
InChI Key |
RLSFDUAUKXKPCZ-UHFFFAOYSA-N |
Canonical SMILES |
C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)C=C(CC3=CC(=C(C=C3F)F)F)N |
Origin of Product |
United States |
Synthesis routes and methods
Procedure details
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