57773-41-8

Basic information

• Product Name: ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate
• Synonyms: 5-Acetyl-2-amino-4-methyl-3-thiophenecarboxylic acid ethyl ester
• CAS NO: 57773-41-8
• Molecular Formula: C₁₀H₁₃NO₃S
• Molecular Weight: 227.28
• Mol File: 57773-41-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 162-164 °C(Solv: ethanol (64-17-5))
• Boiling Point: 405.2°Cat760mmHg
• Flash Point: 198.9°C
• Appearance: /
• Density: 1.239
• Vapor Pressure: 8.93E-07mmHg at 25°C
• Refractive Index: 1.569
• Storage Temp.: 2-8°C
• PKA: -0.70±0.10(Predicted)
• CAS DataBase Reference: ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate(57773-41-8)
• EPA Substance Registry System: ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate(57773-41-8)

Safety Data

• Hazardous Substances Data: 57773-41-8(Hazardous Substances Data)

Usage

Description

Ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate is a chemical compound with the molecular formula C12H15NO3S. It is a derivative of thiophene, a five-membered heterocyclic compound containing sulfur. ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate is characterized by the presence of an acetyl group, an amino group, and an ethyl ester group, which contribute to its versatility as a building block in the synthesis of molecules with potential biological activity. The incorporation of the thiophene ring endows it with unique properties that are valuable in medicinal chemistry and drug discovery.

Uses

Used in Pharmaceutical Research and Synthesis:
Ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate serves as a key intermediate in the development of potential drug candidates. Its diverse functional groups and the thiophene ring allow for the creation of molecules with targeted biological activities, making it a valuable component in the design of new pharmaceutical agents.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate is utilized for its unique structural features that can be exploited to enhance the properties of drug molecules. The thiophene ring, in particular, can impart specific pharmacokinetic and pharmacodynamic characteristics to the molecules in which it is incorporated, potentially leading to improved drug efficacy and safety profiles.
Used in Drug Discovery:
Ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate plays a crucial role in drug discovery, where its structural elements can be modified to explore a wide range of chemical space. ethyl 5-acetyl-2-amino-4-methyl-thiophene-3-carboxylate's adaptability makes it an ideal candidate for high-throughput screening and optimization processes, facilitating the identification of novel therapeutic agents with potential applications across various medical fields.

InChI:InChI=1/C10H13NO3S/c1-4-14-10(13)7-5(2)8(6(3)12)15-9(7)11/h4,11H2,1-3H3

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 123-54-6 acetylacetone 

Downstream Products

• 120456-32-8 5-Acetyl-2-hydroxy-4-methyl-thiophen-3-carbonitril 
• 120456-30-6 2-Amino-5(1-hydrazinoethyl)-4-methyl-thiophen-3-carbonsaeureethylester 
• 1147101-52-7 C₁₀H₁₁N₃O₃S 
• 1219458-66-8 C₂₂H₂₅N₃O₃S 

Relevant articles and documents

Synthesis, pharmacological evaluation, and in-silico studies of thiophene derivatives

The relevance of Retinoic acid receptor-related orphan receptors in cancer progression has sparked interest in developing multifunctional therapeutics. In the search for potentially active novel compounds with anticancer characteristics, the Gewald reaction was employed to develop different thiophene derivatives (8a–8i). Physicochemical and spectroanalytical investigations verified the molecular structures of the synthesized derivatives. Using an in vitro primary anticancer assay, NCI chose all of the synthesized molecules as prototypes and assessed their anticancer efficacy against a panel of various cancer cell lines representing nine distinct neoplasms. The compounds were found to have a wide range of anticancer activity. Following significant anticancer efficacy against all cell lines in the initial screening, compound 8e was chosen for a five-dose test. Compound 8e inhibited growth at concentrations ranging from 0.411 to 2.8 μM. The antioxidant activity of the compounds was further evaluated using the radical scavenging action of the stable DPPH free radical. In comparison to Ascorbic Acid, compounds 8e and 8i showed outstanding antioxidant activity, while the remaining compounds in the series demonstrated acceptable antioxidant activity. In a molecular docking investigation, 8e demonstrated excellent docking scores inside the binding pocket of the specified pdb-id (6q7a), complementing the results of anticancer screening. Based on our results, novel ethyl 5-acetyl-2-amino-4-methylthiophene-3-carboxylate derivatives could be useful in the development of potential anticancer treatments.

Mg/La mixed oxide as an efficient heterogeneous basic catalyst for synthesis of 2-aminothiophenes under microwave irradiation

Microwave-assisted synthesis of 2-aminothiophenes via a Gewald reaction using a heterogeneous strong basic Mg/La mixed oxide catalyst is described.

Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-α-d-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected β-d-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100?mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities.