![molecular formula C19H14F4IN3O6S B8602676 [3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl] trifluoromethanesulfonate](/img/structure/B8602676.png)
[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl] trifluoromethanesulfonate
Overview
Description
[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl] trifluoromethanesulfonate is a complex organic compound with significant potential in various scientific fields. This compound is characterized by its unique structure, which includes a trifluoromethanesulfonic acid ester group, a cyclopropyl ring, and multiple functional groups that contribute to its reactivity and applications.
Preparation Methods
The synthesis of trifluoromethanesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester involves several steps. The synthetic route typically starts with the preparation of the pyrido[2,3-d]pyrimidin core, followed by the introduction of the cyclopropyl group and the 2-fluoro-4-iodophenyl moiety. The final step involves the esterification with trifluoromethanesulfonic acid. Reaction conditions often include the use of strong acids or bases, high temperatures, and specific catalysts to ensure the desired product is obtained with high purity .
Chemical Reactions Analysis
[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl] trifluoromethanesulfonate undergoes various chemical reactions, including:
Oxidation: This compound can be oxidized using strong oxidizing agents, leading to the formation of corresponding oxides.
Reduction: Reduction reactions can be performed using reducing agents like lithium aluminum hydride, resulting in the formation of reduced derivatives.
Substitution: The compound can undergo nucleophilic substitution reactions, particularly at the iodine and fluorine positions, leading to the formation of various substituted products
Scientific Research Applications
This compound has a wide range of applications in scientific research, including:
Chemistry: It is used as a building block in the synthesis of more complex molecules and as a reagent in various organic reactions.
Biology: The compound’s unique structure allows it to interact with biological molecules, making it useful in the study of enzyme mechanisms and protein-ligand interactions.
Industry: Used in the development of new materials and as a catalyst in industrial processes
Mechanism of Action
The mechanism of action of trifluoromethanesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester involves its interaction with specific molecular targets. The compound can bind to enzymes and receptors, altering their activity and leading to various biological effects. The pathways involved often include signal transduction and metabolic processes .
Comparison with Similar Compounds
Compared to other similar compounds, trifluoromethanesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester stands out due to its unique combination of functional groups and structural features. Similar compounds include:
- 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl trifluoromethanesulfonate
- 3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl 4-methylbenzenesulfonate .
These compounds share similar core structures but differ in their ester groups, leading to variations in their reactivity and applications.
Properties
Molecular Formula |
C19H14F4IN3O6S |
|---|---|
Molecular Weight |
615.3 g/mol |
IUPAC Name |
[3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl] trifluoromethanesulfonate |
InChI |
InChI=1S/C19H14F4IN3O6S/c1-8-14(33-34(31,32)19(21,22)23)13-15(25(2)16(8)28)27(12-6-3-9(24)7-11(12)20)18(30)26(17(13)29)10-4-5-10/h3,6-7,10H,4-5H2,1-2H3 |
InChI Key |
MYSICWOANMWNQI-UHFFFAOYSA-N |
Canonical SMILES |
CC1=C(C2=C(N(C1=O)C)N(C(=O)N(C2=O)C3CC3)C4=C(C=C(C=C4)I)F)OS(=O)(=O)C(F)(F)F |
Origin of Product |
United States |
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