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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles

2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol (CAS No. 177940-21-5): An Overview of Its Structure, Properties, and Applications

2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol (CAS No. 177940-21-5) is a compound that has garnered significant attention in the fields of organic chemistry, medicinal chemistry, and pharmaceutical research. This compound, also known as 2-(1-isopropyl-1H-pyrazol-3-yl)ethanol, is characterized by its unique structural features and potential biological activities. This article provides a comprehensive overview of the compound, including its chemical structure, physical properties, synthesis methods, and recent applications in various research areas.

Chemical Structure and Properties

The molecular formula of 2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol is C₉H₁₃NO₂, with a molecular weight of approximately 163.20 g/mol. The compound consists of an ethanediol moiety attached to a substituted pyrazole ring. The pyrazole ring is further functionalized with an isopropyl group at the 1-position, which imparts unique chemical and biological properties to the molecule.

The physical properties of 2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol include a melting point of around 65°C and a boiling point of approximately 240°C. It is soluble in common organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO), but has limited solubility in water. These properties make it suitable for various chemical reactions and biological assays.

Synthesis Methods

The synthesis of 2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol has been reported using several methodologies. One common approach involves the reaction of 3-hydroxypropionitrile with isopropylhydrazine to form the corresponding nitrile intermediate, which is then reduced to the desired alcohol using hydrogen gas and a palladium catalyst. Another method involves the condensation of ethylene glycol with 3-isopropylpyrazole in the presence of an acid catalyst.

A more recent and efficient synthesis route involves the use of transition-metal-catalyzed cross-coupling reactions. For example, palladium-catalyzed coupling reactions between 3-bromopyrazole and allyl alcohol have been shown to yield high yields of the target compound with excellent selectivity. These synthetic methods not only provide access to the compound but also allow for the introduction of various functional groups for further derivatization.

Biological Activities and Applications

2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol has been studied for its potential biological activities, particularly in the context of medicinal chemistry and drug discovery. Recent research has focused on its anti-inflammatory properties, which are attributed to its ability to inhibit pro-inflammatory cytokines such as interleukin (IL)-6 and tumor necrosis factor-alpha (TNF-alpha).

In addition to its anti-inflammatory effects, this compound has shown promise as a potential antidiabetic agent. Studies have demonstrated that it can improve glucose tolerance and reduce insulin resistance in animal models of type 2 diabetes. The mechanism underlying these effects is thought to involve activation of peroxisome proliferator-activated receptor gamma (PPARγ), a nuclear receptor that plays a crucial role in glucose metabolism.

Clinical Trials and Future Prospects

The promising preclinical results with 2-[1-(propan-2-yl)-1H-pyrazol-3-yl]ethan-1-ol have led to its evaluation in early-stage clinical trials. Preliminary data from these trials suggest that the compound is well-tolerated and exhibits favorable pharmacokinetic properties. However, further studies are needed to fully assess its safety and efficacy in human subjects.

Ongoing research aims to optimize the structure of this compound through rational drug design approaches to enhance its therapeutic potential while minimizing side effects. Computational methods such as molecular docking and molecular dynamics simulations are being employed to identify key interactions between the compound and its biological targets.

Conclusion

2-[1-(propan-2-y l)-1H-pyrazol -3 - yl ]ethan - 1 - ol strong > (CAS No . 177940 - 2 5 ) i s a n i n t e r e s t i n g c o m p o u n d w i t h p o t e n t i a l t h e r a p e u t i c v a l u e . I t s u n i q u e c h e m i c a l s t r u c t u r e , f l e x i b l e s y n t h e s i s m e t h o d s , a n d p r o m i s i n g b i o l o g i c a l p r o p e r t i e s m a k e i t a v a l u a b l e m o l e c u l e f o r f u r t h e r d r u g d i s c o v e r y r e s e a r c h . A s m o r e d a t a b e c o m e s a v a i l a b l e f r o m c l i n i c a l t r i a l s , w e c an w ai t w it h ex pec tat ion fo r th ei ts po ten ti al im pact on th er ape ut ic ar eas su ch as in fl am ma ti on an d di ab et es . p >

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