19156-47-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 5-(2-acetoxyethyl)-4-Methylthiophene-3-carboxylate is used as a synthetic intermediate for the development of new pharmaceuticals. Its unique chemical structure allows it to be incorporated into more complex molecules, potentially leading to the discovery of novel drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, ethyl 5-(2-acetoxyethyl)-4-Methylthiophene-3-carboxylate is utilized as a precursor in the synthesis of various agrochemicals. Its chemical properties and structure make it suitable for the development of new pesticides, herbicides, and other agricultural chemicals that can enhance crop protection and yield.
Both in the pharmaceutical and agrochemical industries, the use of ethyl 5-(2-acetoxyethyl)-4-Methylthiophene-3-carboxylate as a building block is driven by its potential to contribute to the creation of innovative and effective products, thanks to its unique chemical characteristics and structural features.

Upstream product

• 1012795-36-6 C₁₄H₂₄O₆S 
• 13051-49-5 5-Acetoxy-3-chloropentan-2-one 
• 13045-13-1 3-chloro-3-acetylpropanol 
• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 334687-32-0 Ethyl 5-(2-acetoxyethyl)-2-bromo-4-methylthiophene-3-carboxylate 
• 334687-31-9 Ethyl 6-acetoxy-2-cyano-3-methyl-4-chlorohex-2-enoate 
• 15854-07-6 Ethyl 6-acetoxy-2-cyano-3-methylhex-2-enoate 
• 17423-23-3 Ethyl 5-(2-acetoxyethyl)-2-amino-4-methylthiophene-3-carboxylate 

Relevant academic research and scientific papers

Differences in the efficiency of 3-deazathiamine and oxythiamine pyrophosphates as inhibitors of pyruvate dehydrogenase complex and growth of HeLa cells in?vitro

Oxythiamine (OT) and 3-deazathiamine (DAT) are the antimetabolites of thiamine. The aim of study was to compare the effects of OT and DAT pyrophosphates (-PP) on the kinetics of mammalian pyruvate dehydrogenase complex (PDHC) and the in?vitro culture of HeLa cells. The kinetic study showed that 3-deazathiamine pyrophosphate (DATPP) was a much stronger competitive inhibitor (Ki = 0.0026 μM) of PDHC than OTPP (Ki = 0.025 μM). Both Ki values were much lower versus K m for thiamine pyrophosphate (0.06 μM). However, DATPP added to the culture medium for the HeLa cells culture did not hamper the rate of cell growth and showed not significant impact on the viability of the cells, whereas OTPP and OT showed a significant cytostatic effect. The differences between the thiamine antivitamins in their effect on cell growth in?vitro may be due to differences in physicochemical properties and difficulty in DAT transport across the cell membrane.

Non-charged thiamine analogs as inhibitors of enzyme transketolase

Inhibition of the thiamine-utilizing enzyme transketolase (TK) has been linked with diminished tumor cell proliferation. Most thiamine antagonists have a permanent positive charge on the B-ring, and it has been suggested that this charge is required for diphosphorylation by thiamine pyrophosphokinase (TPPK) and binding to TK. We sought to make neutral thiazolium replacements that would be substrates for TPPK, while not necessarily needing thiamine transporters (ThTr1 and ThTr2) for cell penetration. The synthesis, SAR, and structure-based rationale for highly potent non-thiazolium TK antagonists are presented.

Synthesis of 3-deazathiamine

An efficient ten-step synthesis of deazathiamine is described. The synthesis starts from commercially available α-acetyl-γ-butyrolactone and proceeds via deamination of the key aminothiophene 6. The Gewald synthesis of thiophenes is shown to give a mixture of isomeric products with the unsymmetric ketone used here and so a modified procedure giving a single isomer is developed.