158062-71-6 | 4-(TRIFLUOROMETHYL)NICOTINAMIDE

CAS:158062-71-6 | 4-(TRIFLUOROMETHYL)NICOTINAMIDE,Description

4-(Trifluoromethyl)nicotinamide is a chemical compound that is part of a broader class of nicotinamide derivatives. These compounds are of significant interest in the pharmaceutical and agrochemical industries due to their potential biological activities. The trifluoromethyl group in particular is known for enhancing the metabolic stability and bioavailability of pharmaceuticals, making 4-(Trifluoromethyl)nicotinamide a valuable intermediate for drug development.

Synthesis Analysis

The synthesis of 4-(Trifluoromethyl)nicotinamide derivatives can involve various starting materials and optimized reactions. For instance, the synthesis of 4-(Trifluoromethyl)nicotinic acid, a related compound, was achieved using ethyl 4,4,4-trifluoroacetoacetate and cyanoacetamide through a series of reactions including cyclization, chlorination, hydrogenolysis, and hydrolysis, with a total yield of 38.6%. Another related compound, methyl 6-chloro-5-(trifluoromethyl)nicotinate, was synthesized using a trifluoromethylation process that is both safe and economical, highlighting the importance of developing efficient synthetic routes for these compounds.

Molecular Structure Analysis

The molecular structure of 4-(Trifluoromethyl)nicotinamide derivatives is characterized by the presence of a nicotinamide core, which is a nitrogen-containing heterocycle, and a trifluoromethyl group. The presence of these functional groups is crucial for the biological activity of these compounds. For example, the trifluoromethyl group is known to enhance binding interactions with biological targets.

Chemical Reactions Analysis

Nicotinamide derivatives, including those with the 4-(trifluoromethyl) group, can participate in various chemical reactions that are essential for their biological activity. For instance, some nicotinamide derivatives have been shown to inhibit tubulin polymerization, which is a critical process in cell division and a target for anticancer agents. The chemical reactivity of these compounds is also influenced by the presence of other substituents, which can be strategically modified to improve their biological efficacy.

Physical and Chemical Properties Analysis

The physical and chemical properties of 4-(Trifluoromethyl)nicotinamide derivatives are influenced by the trifluoromethyl group, which imparts unique characteristics such as increased lipophilicity and metabolic stability. These properties are important for the pharmacokinetic profile of potential drug candidates. The specific physical and chemical properties of these compounds would be determined through experimental studies, including solubility, melting point, and stability tests.

Scientific Research Applications

Role in Cell Survival and Differentiation

Nicotinamide, a form of vitamin B3, has shown potential in promoting cell survival and differentiation in human pluripotent stem cells. It functions as a kinase inhibitor, impacting the phosphorylation of myosin light chain and actomyosin contraction, leading to improved cell survival post-individualization (Meng et al., 2018).

Impact on Cellular Energy Metabolism

Nicotinamide influences oxidative stress and modulates pathways linked to cellular survival and death. It plays a crucial role in cellular energy metabolism, impacting physiology, and has shown promise in treatments for immune dysfunction, diabetes, and aging-related diseases (Maiese et al., 2009).

Safety And Hazards

When handling 4-(Trifluoromethyl)nicotinamide, it is advised to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes. Personal protective equipment should be used, and adequate ventilation should be ensured.

More Information