89499-38-7

Usage

Uses

Used in Pharmaceutical Industry:
4-AMINOTHIOPHENE-2-CARBOXYLIC ACID is used as a key intermediate in the synthesis of (S)-4-Amino-4,-dihydro-2-thiophenecarboxylic Acid, a heterocyclic mimic of the natural product Gabaculine (G111000). Gabaculine is a mechanism-based inactivator of γ-aminobutyric acid aminotransferase (GABA-AT), an enzyme involved in the synthesis of GABA, a major inhibitory neurotransmitter in the central nervous system. This makes 4-AMINOTHIOPHENE-2-CARBOXYLIC ACID an important component in the development of drugs targeting neurological disorders and conditions related to GABAergic signaling.
Used in Agrochemical Industry:
4-AMINOTHIOPHENE-2-CARBOXYLIC ACID is also utilized as a building block in the synthesis of agrochemicals, such as herbicides and insecticides. Its unique chemical properties allow for the development of novel compounds with improved efficacy and selectivity, contributing to more effective and environmentally friendly pest control solutions.

InChI:InChI=1/C5H5NO2S/c6-3-1-4(5(7)8)9-2-3/h1-2H,6H2,(H,7,8)

Upstream product

• 6317-37-9 5-nitrothiophene-2-carboxylic acid 
• 527-72-0 2-thiophenylcarboxylic acid 
• 13138-70-0 4-nitro-2-thiophenecarboxylic acid 

Relevant academic research and scientific papers

Mechanism of inactivation of γ-aminobutyric acid aminotransferase by (S)-4-amino-4,5-dihydro-2-thiophenecarboxylic acid

(S)-4-Amino-4,5-dihydro-2-thiophenecarboxylic acid ((S)-6) was previously synthesized (Adams, J. L.; Chen, T. M.; Metcalf, B. W. J. Org. Chem. 1985, 50, 2730-2736.) as a heterocyclic mimic of the natural product gabaculine (5-amino-1,3-cyclohexadienylcarboxylic acid), a mechanism-based inactivator of γ-aminobutyric acid aminotransferase (GABA-AT) (Rando, R. R. Biochemistry 1977, 16, 4604). Inactivation of GABA-AT by (S)-6 is time-dependent and protected by substrate. Two methods were utilized to demonstrate that, in addition to inactivation, about 0.7 equiv per inactivation event undergoes transamination. Inactivation results from the reaction of (S)-6 with the pyridoxal 5-phosphate (PLP) cofactor. The adduct was isolated and characterized by ultraviolet-visible spectroscopy, electrospray mass spectrometry, and tandem mass spectrometry. All of the results support a structure (11) that derives from the predicted aromatization inactivation mechanism (Scheme 2) originally proposed by Metcalf and co-workers for this compound. This is only the third example, besides gabaculine and L-cycloserine, of an inactivator of a PLP-dependent enzyme that acts via an aromatization mechanism.

Carbapenem antibiotic compounds

The present invention relates to carbapenems and provides a compound of the formula (I) STR1 wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; R3 is hydrogen or C1-4 alkyl; and the thienyl ring is optionally further substitued by one or two substituents selected from halo, cyano, C1-4 alkyl, nitro, hydroxy, carboxy, C1-4 alkoxy, trifluoromethyl, C1-4 alkoxycarbonyl, amino, C1-4 alkylamino, di-C1-4 alkylamino, sulfonic acid, C1-4 alkylS(O)n -- (wherein n is 0-2), C1-4 alkanoylamino, C1-4 alkanoyl(N-C1-4 alkyl)amino, carbamoyl, C1-4 alkylcarbamoyl, di-C1-4 alkylcarbamoyl and N-C1-4 alkanesulfonamido; or by a tetramethylene group attached to adjacent carbon atoms on the thienyl ring; or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them are also described.

Antibiotic penem compounds

The present invention provides a compound of the formula (I) STR1 wherein: R1 is 1-hydroxyethyl, 1-fluoroethyl or hydroxymethyl; R2 is hydrogen or C1-4 alkyl; Z is carboxy, sufonic acid, tetrazol-5-yl or C 1-4 alkylsulfonylcarbamoyl (--CONHSO2 C1-4 alkyl); A is a phenyl or thienyl ring; and A is optionally further substituted by one or two substituents or a pharmaceutically acceptable salt or in vivo hydrolysable ester thereof. Processes for their preparation, intermediates in their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.