23906-20-9

Usage

Uses

Used in Pharmaceutical Industry:
DIETHYL 2-ACETAMIDO-2-(BENZO(B)THIOPHENE-3-YLMETHYL)MALONATE is used as a pharmaceutical intermediate for the synthesis of potentially bioactive substances. Its unique benzothiophene ring structure allows for the development of diverse biologically active molecules, which can be further explored for their pharmacological and biochemical properties.
Used in Agrochemical Industry:
DIETHYL 2-ACETAMIDO-2-(BENZO(B)THIOPHENE-3-YLMETHYL)MALONATE is also used as an intermediate in the synthesis of agrochemicals. Its unique structure can contribute to the development of new agrochemicals with improved efficacy and selectivity.
Note: The information provided in this summary is based on the chemical name given. For accurate and comprehensive information, it is essential to refer to the specific material safety data sheet and other reliable sources.

InChI:InChI=1/C18H21NO5S/c1-4-23-16(21)18(19-12(3)20,17(22)24-5-2)10-13-11-25-15-9-7-6-8-14(13)15/h6-9,11H,4-5,10H2,1-3H3,(H,19,20)

Upstream product

• 3216-47-5 3-chloromethylbenzothiophene 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 1956-23-6 (R)-α-amino-3-[1]benzothiophene-3-ylpropionic acid 
• 154902-51-9 (2S)-2-[(tert-butoxycarbonyl)amino]-3-(benzo[b]thiophen-3-yl)propanoic acid 
• 166519-79-5 (2S,4R)-2-[(S)-2-Benzo[b]thiophen-3-yl-1-(benzyl-methyl-carbamoyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 158574-74-4 N²-Boc-N-methyl-N-(phenylmethyl)-3-(3-benzothienyl)-L-alaninamide 
• 72120-71-9 (S)-2-amino-3-<1>benzothiophene-3-ylpropionic acid 

Relevant academic research and scientific papers

Chemoenzymatic preparation of enantiopure l-benzofuranyl- and l-benzo[b]thiophenyl alanines

Lipase mediated DKR followed by a chemical and an enzymatic hydrolytic step were combined for the synthesis of enantiopure l-benzofuranyl- and l-benzothienyl alanines.

The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase from parsley

Acrylic acids and alanines substituted with heteroaryl groups at the β-position were synthesized and spectroscopically characterized (UV, HRMS, 1H NMR, and 13C NMR spectroscopy). The heteroaryl groups were furanyl, thiophenyl, benzofuranyl, and benzothiophenyl and contained the alanyl side chains either at the 2- or 3-positions. While the former are good substrates for phenylalanine ammonia lyase (PAL), the latter compounds are inhibitors. Exceptions are thiophen-3-yl-alanine, a moderate substrate and furan-3-yl-alanine, which is inert. Possible reasons for these exceptions are discussed. Starting from racemic het eroaryl-2-alanines their D-enantiomers were prepared by using a stereodestructive procedure. From the heteroaryl-2- acrylates, the L-enantiomers of the heteroaryl-2-alanines were prepared at high ammonia concentration. These results can be best explained by a Friedel - Crafts-type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.

Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds

As an extension of our studies on discovering a novel substance P (SP) antagonist, we modified the previously reported dipeptide, N2-2-(1H-indol-3-ylcarbonyl)-L-lysyl>-N-methyl-N-(phenylmethyl)-L-phenylalaninamide (2b).The lysine part in 2b was first optimized to a (2S,4R)-hydroxyproline derivative (3h), which is 2-fold more potent than 2b in SP binding assay using guinea pig lung membranes.Next we modified the 1H-indol-3-ylcarbonyl part in 3h.Introduction of a methyl group at the indole nitrogen enhanced the oral activity, while retaining the binding activity.Finally, we modified the phenylalanine part to culminate in the most potent compound 7k (FK888), which is a potent SP antagonist with NK1 selectivity as well as oral activity.