5-(2,3-Dihydro-2-thioxo-4-thiazolyl)-2-thiophenecarboxamide
[CAS# 52560-89-1]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 5-(2,3-Dihydro-2-thioxo-4-thiazolyl)-2-thiophenecarboxamide
• Synonyms: NSC 317939
• Molecular Formula: C₈H₆N₂OS₃
• Molecular Weight: 242.34
• CAS Registry Number: 52560-89-1
• SMILES: C1=C(SC(=C1)C(=O)N)C2=CSC(=S)N2

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.807, Calc.^*
• Boiling Point: 471.1±55.0 ºC (760 mmHg), Calc.^*
• Flash Point: 238.7±31.5 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovory and Applicatios

5-(2,3-Dihydro-2-thioxo-4-thiazolyl)-2-thiophenecarboxamide, commonly referred to as "thiazolylthiophenecarboxamide", is a class of compounds characterized by thiazole and thiophene rings. The discovery of thiazolylthiophenecarboxamides stems from research efforts to create novel heterocyclic compounds with potential biological activity. Heterocyclic rings are characterized by at least one atom other than carbon in the ring and are important in medicinal chemistry due to their diverse biological properties. Thiazole and thiophene rings have been the focus of extensive research due to their ability to impart specific pharmacological properties.

The synthesis of 5-(2,3-dihydro-2-thioxo-4-thiazolyl)-2-thiophenecarboxamides typically involves a condensation reaction between a thioamide and a haloketone to form the thiazole ring, followed by coupling of the thiazole intermediate with a thiophenecarboxylic acid derivative using standard amide bond formation techniques. The synthesis emphasizes controlling the reaction conditions to obtain the desired functional group and maintain heterocyclic integrity.

Thiazolylthiophenecarboxamides show potential in drug development, particularly as inhibitors of certain enzymes and receptors. Its bicyclic system provides a versatile scaffold for interaction with biological targets, making it a candidate for drug design in areas such as anti-inflammatory, antibacterial, and anticancer therapy.

One notable application is its role as a lead compound in the development of enzyme inhibitors. The thiazole ring contains sulfur and nitrogen atoms that can interact with the active site of an enzyme, inhibiting its function. This makes the compound valuable in the design of drugs that target specific enzymes involved in disease pathways, such as those regulating inflammation or bacterial cell wall synthesis.

In addition, the thiophene ring helps the compound modulate biological activity by interacting with various receptors. Its incorporation into drug molecules can enhance binding affinity and selectivity, leading to the development of more effective and safer therapeutic agents.

In chemical research, thiazolyl-thiophenecarboxamide is a model compound for studying the reactivity and properties of heterocyclic systems. Its synthesis and characterization provide insights into the behavior of thiazole and thiophene rings under different chemical conditions. This knowledge is valuable for developing new synthetic methods and understanding the basic principles of heterocyclic chemistry.

The unique structure of this compound also makes it an important tool in materials science. Its heterocyclic ring provides multiple chemical modification sites, allowing the development of functional materials with specific properties, such as conductive polymers or photoactive materials.

Ongoing research focuses on exploring its full potential in drug discovery and materials science. Efforts are underway to optimize its synthesis, explore its derivatives, and evaluate its biological activities. These studies aim to enhance its therapeutic applications and expand its utility in various areas of chemical research.