13138-70-0

Usage

Uses

Used in Pharmaceutical Industry:
4-Nitro-2-thiophenecarboxylic Acid is used as a key intermediate in the synthesis of pharmaceutical compounds for the development of highly potent and selective hetaryl ureas. These hetaryl ureas act as integrin αVβ3-receptor antagonists, which play a significant role in various biological processes and therapeutic applications.
In the synthesis of integrin αVβ3-receptor antagonists, 4-Nitro-2-thiophenecarboxylic Acid is used to create molecules that can effectively target and inhibit the integrin αVβ3 receptor. This receptor is known to be involved in various pathological conditions, including angiogenesis, tumor growth, and metastasis. By inhibiting this receptor, the synthesized pharmaceutical compounds can potentially be used in the treatment of diseases such as cancer, where the inhibition of angiogenesis and tumor growth is crucial for therapeutic success.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 577, 1955 DOI: 10.1021/ja01608a017

InChI:InChI=1/C5H3NO4S/c7-5(8)4-1-3(2-11-4)6(9)10/h1-2H,(H,7,8)

Upstream product

• 527-72-0 2-thiophenylcarboxylic acid 
• 4282-34-2 Dimethyl thiophene-2,5-dicarboxylate 
• 57784-57-3 (Z)-thiophene-2-carbaldehyde oxime 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 24647-78-7 methyl 4-nitrothiophene-2-carboxylate 
• 42137-24-6 4-nitrothiophene-2-carbonitrile 
• 57500-53-5 4-nitrothiophene-2-carbaldehyde 
• 1003-31-2 thiophene-2-carbonitrile 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 89499-38-7 4-amino-2-thiophenecarboxylic acid 
• 56921-01-8 5-methyl-4-nitro-thiophene-2-carboxylic acid methyl ester 
• 822-84-4 3-nitrothiophene 
• 42791-51-5 2-acetyl-4-nitrothiophene 

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.

Crystal engineering of cadmium coordination polymers decorated with nitro-functionalized thiophene-2,5-dicarboxylate and structurally related bis(imidazole) ligands with varying flexibility

A new thiophene-2,5-dicarboxylic acid derivative, 3-nitro-thiophene-2,5-dicarboxylic acid (H2ntdc), was synthesized. Reaction of H2ntdc with cadmium diacetate dihydrate and structurally related bis(imidazole) ligands with varying flexibility gave rise to four new CPs, formulated as {[Cd(ntdc)(bmip)(H2O)](H2O)}n (1), {[Cd(ntdc)(bmib)](H2O)}n (2), [Cd(ntdc)(beip)]n (3) and [Cd(ntdc)(beib)]n (4) [bmip = 1,3-bis(2-methylimidazolyl)propane, bmib = 1,4-bis(2-methylimidazolyl)butane, beip = 1,3-bis(2-ethylimidazolyl)propane and beib = 1,4-bis(2-ethylimidazolyl)butane]. Moreover, a new compound {[Cd(ntc)2(bmib)](H2O)}n (5) (Hntc = 4-nitro-thiophene-2-carboxylic acid) involving in situ ligand synthesis was prepared. Structural analyses reveal that 1 features a two-dimensional (2D) 44-sql layer, and is further stacked via hydrogen bonding interactions to give a three-dimensional (3D) hydrogen-bonded architecture. 2 displays a 3,4-connected 3D network with ins type topology, which is composed of 2D hcb topological networks pillared by the bmib ligands. 3 exhibits a 3,5-connected 3D network with a (42·63·85)(42·6) topology. 4 possesses a 3-fold interpenetrating 3D net with a dmp topology. 5 can be described as a one-dimensional (1D) chain structure, and is further assembled into a 2D hydrogen-bonded 44sql layer. Factors that influence the structural assembly of 1-4, as well as the formation of 5 involving the in situ produced Hntc ligand, are discussed. Moreover, structure stabilities and photoluminescence properties of the complexes were also investigated.

Method for rapidly preparing 4-nitrothiophene-2-formic acid based on microchannel reaction technology

The invention discloses a method for rapidly preparing 4-nitrothiophene-2-formic acid based on a micro-channel reaction technology. The method involves a nitration reaction. The method specifically comprises the following steps of: continuously pumping a sulfuric acid solution of thiophene-2-formic acid and nitric acid or nitric acid and sulfuric acid mixture into a micro-channel reactor through a sample injection pump according to a certain equivalent proportion, and performing mixing; and carrying out an electrophilic substitution reaction of nitroacyl cations on thiophene rings at a certain temperature to generate the product 4-nitrothiophene-2-formic acid. By applying the microchannel reaction technology, the synthetic method which is safer, more efficient, simple and convenient to operate and low in cost is provided, and the high-conversion-rate product 4-nitrothiophene-2-formic acid is obtained under the controllable continuous condition of the nitration reaction.

Raltitrexed pharmaceutical composition and preparation method thereof

The invention relates to a raltitrexed pharmaceutical composition which is high in safety and a preparation method thereof. The raltitrexed pharmaceutical composition comprises raltitrexed and thiophene related substances, wherein the content of the thiophene related substances is not higher than 0.3%. The raltitrexed pharmaceutical composition is good in safety, effectiveness and stability and can relieve the blood toxicity of the raltitrexed to a certain degree.

Impurity B of raltitrexed, and preparation method and application thereof

The invention discloses a potential blood system toxic impurity B of raltitrexed, a preparation method thereof, and a use of the impurity B as an impurity reference substance.

ANTI-CANCER DRUGS AND USES RELATING THERETO FOR METASTATIC MALIGNANT MELANOMA AND OTHER CANCERS

The present invention discloses triazene analogs of the general formula (I) and formula (II), their tautomeric forms, stereoisomers, polymorphs, hydrates, solvates, and pharmaceutically acceptable salts thereof for the metastatic malignant melanoma and other cancers including but not limited to lymphomas, sarcomas, carcinomas, and gliomas. The invention further discloses a process for the preparation of the above said triazene analogs of formula (I) and formula (II), and their pharmaceutically acceptable compositions.

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.

THE PREPARATION OF 2-(HETEROCYCLIC)THIENOPYRIDINE DERIVATIVES

The preparation of a series of 2-(heterocyclic)-4-ethyl-4,7-dihydro-7-oxothienopyridine-6-carboxylic acids (5j-l) by aminolysis of the corresponding 2-bromo derivative (5i) is described.None of the compounds (5j-l) showed any interesting antibacterial activity.