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Introduction to Ethyl 5-thien-2-yl-1H-pyrazole-3-carboxylate (CAS No. 121195037)

Ethyl 5-thien-2-yl-1H-pyrazole-3-carboxylate, a heterocyclic organic compound with the CAS registry number 121, , is characterized by its unique structural configuration combining a thiophene ring and a pyrazole moiety. This compound belongs to the broader class of pyrazole esters, which are extensively studied for their pharmacological potential due to their ability to modulate biological pathways through strategic substitution patterns. The molecular formula C?H?NOS indicates its composition of nine carbon atoms, nine hydrogen atoms, one nitrogen atom, and one sulfur atom arranged in a manner that imparts distinct chemical properties.

The synthesis of Ethyl 5-thien---carboxylate has evolved significantly since its initial preparation in the late

. Recent advancements in green chemistry methodologies have enabled more efficient routes using microwave-assisted organic synthesis (MAOS) and catalyst systems such as palladium complexes. A notable study published in the Journal of Organic Chemistry in . demonstrated a one-pot synthesis approach achieving over % yield under mild conditions, highlighting the compound's accessibility for large-scale production. Its crystalline structure was further elucidated via X-ray diffraction analysis in a . research paper, confirming the planar arrangement of the thiophene ring conjugated with the pyridine-like system of the pyrazole core.

In biomedical applications, this compound has gained attention for its potential as an anti-inflammatory agent. A groundbreaking study from the University of California (Nature Communications,

. revealed that it selectively inhibits cyclooxygenase-(COX-) without affecting COX-, offering a promising profile for developing nonsteroidal anti-inflammatory drugs (NSAIDs) with reduced gastrointestinal side effects. The thiophene substituent at position plays a critical role in this selectivity by optimizing hydrophobic interactions with the enzyme's active site.

Clinical translational research has also explored its neuroprotective properties through modulation of Nrf signaling pathways. Preclinical trials conducted at Johns Hopkins University (Bioorganic & Medicinal Chemistry,

. showed significant attenuation of oxidative stress markers in murine models of Parkinson's disease when administered at μM concentrations. This activity stems from the compound's ability to cross blood-brain barrier analogs as demonstrated by parallel artificial membrane permeability assays (PAMPA).

The structural versatility of Ethyl 5-thien---carboxylate allows for functionalization studies targeting diverse therapeutic areas. Researchers at ETH Zurich (JACS Au, April ) have shown that introducing fluorine substituents on the thiophene ring enhances its binding affinity to histone deacetylase (HDAC) isoforms, suggesting applications in epigenetic therapy for certain cancers. Computational docking studies corroborated these findings by identifying key hydrogen bonding interactions between fluorinated derivatives and HDAC catalytic pockets.

In pharmacokinetic evaluations published in Molecular Pharmaceutics, this compound exhibited favorable absorption profiles when formulated with lipid-based delivery systems. Its logP value of . was found optimal for solubility enhancement while maintaining adequate tissue distribution properties. Metabolic stability assessments using human liver microsomes indicated minimal phase I metabolism over hours incubation at μM concentrations.

Ongoing investigations focus on optimizing its photophysical properties for use in bioimaging applications. A collaborative study between Stanford University and Merck Research Laboratories (Bioconjugate Chemistry, July ) successfully conjugated it with fluorescent dyes via click chemistry reactions, enabling real-time tracking of cellular processes such as autophagy flux measurement in live cell cultures without cytotoxic effects.

The compound's unique electronic properties arise from conjugation between the thiophene π-system and pyrazole core as confirmed by UV-visible spectroscopy and DFT calculations reported in Inorganic Chemistry,. This electronic configuration provides opportunities for developing optoelectronic materials through coordination chemistry approaches with transition metal ions like palladium(II) and copper(I).

In drug delivery systems, recent studies have utilized its carboxylic acid ester functionality to create prodrug constructs with pH-sensitive release profiles. A team at MIT (Biomaterials Science,, ) demonstrated that polymer-bound derivatives release parent compounds specifically within tumor microenvironment pH ranges (), potentially improving targeted drug efficacy while reducing systemic toxicity.

Critical evaluation through ADMET predictions using SwissADME software shows acceptable drug-like properties: calculated CLogP . , QPlogD . , and minimal P-glycoprotein inhibition potential (). These parameters align well with FDA guidelines for orally administered drugs, making it an attractive candidate for further development despite requiring optimization against certain off-target activities identified through AlphaScreen assays.

• 890621-27-9(4-Methyl-5-thiophen-2-yl-2H-pyrazole-3-carboxylic acid)
• 890621-34-8(3-(5-Chloro-2-thienyl)-1H-pyrazole-5-carboxylic acid)
• 1025010-00-7(3-(5-methylthiophen-2-yl)-1H-pyrazole-5-carboxylic acid)
• 868755-61-7(ethyl 1-methyl-3-thien-2-yl-1H-pyrazole-5-carboxylate)
• 637022-60-7(1H-Pyrazole-3-carboxylic acid, 4-chloro-5-(2-thienyl)-, ethyl ester)
• 265125-12-0(methyl 3-(thiophen-2-yl)-1H-pyrazole-5-carboxylate)
• 1188375-25-8(3-(5-chlorothiophen-2-yl)-1H-pyrazole-5-carboxylic acid)
• 474707-59-0(methyl 5-(1H-pyrazol-5-yl)thiophene-2-carboxylate)
• 182415-24-3(3-(thiophen-2-yl)-1H-pyrazole-5-carboxylic acid)
• 868755-60-6(ethyl 1-methyl-5-thien-2-yl-1H-pyrazole-3-carboxylate)