79128-68-0

Usage

Uses

Used in Medicinal Chemistry:
3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester is used as a building block for the synthesis of biologically active molecules in medicinal chemistry. Its unique structure and functional groups contribute to the development of new pharmaceutical agents with potential therapeutic applications.
Used in Pharmaceutical Research:
In pharmaceutical research, 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester is utilized as a key intermediate in the synthesis of drug candidates. Its specific properties and reactivity in chemical reactions enable the creation of novel compounds with potential therapeutic effects.
Used in Chemical Reactions and Processes:
3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester is employed in various chemical reactions and processes to modify or functionalize other molecules. Its versatility and reactivity make it a valuable tool in the synthesis of complex organic compounds for diverse applications.

InChI:InChI=1S/C8H6F3NO3S/c1-15-6(13)5-4(2-3-16-5)12-7(14)8(9,10)11/h2-3H,1H3,(H,12,14)

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 852330-31-5 5-bromo-3-(2,2,2-trifluoracetamido)thiophene-2-carboxylic acid methyl ester 
• 107818-55-3 3-amino-5-bromo-thiophene-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Solid-phase synthetic method for N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives

Herein, we describe a solid-phase synthetic method for synthesizing N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The derivatives consist of the biologically active 6-phenylthieno[3,2-d]pyrimidine scaffold. The template mediated synthetic strategy involving Suzuki coupling reactions between methyl 3-amino-5-bromothiophene-2-carboxylate and arylboronic acids afforded methyl 3-amino-5-arylthiophene-2-carboxylates. Cyclocondensation reactions involving methyl 3-amino-5-arylthiophene-2-carboxylates and methyl cyanoformate afforded esters, that when subjected to hydrolysis reactions yielded 6-aryl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-carboxylic acids (template compounds). These carboxylic acid templates were coupled with primary alkylamine-loaded acid-sensitive methoxybenzaldehyde (AMEBA) resins. The amide coupling reactions were followed by direct amination reactions mediated by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP). The compounds were subsequently cleaved from the solid support, purified using the reverse phase-high performance liquid chromatography technique (RP-HPLC), and passed through a strong anion exchange (SAX) resin pretreated with water to yield the N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The reaction conditions for the solid-phase transformations were optimized using a solution-phase model using 2,4-dimethoxybenzyl-protected isobutylamine as a reactant. 2,4-Dimethoxybenzyl-protected isobutylamine, and not AMEBA resin-loaded isobutylamine was used during the process. Substituent variation experiments were performed using 6-aryl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-carboxylic acids and a variety of primary and secondary amine building blocks. Additionally, we could include the Suzuki coupling step in a modified solid-phase synthetic sequence.

Discovery of Novel Thiophene-Based, Thumb Pocket 2 Allosteric Inhibitors of the Hepatitis C NS5B Polymerase with Improved Potency and Physicochemical Profiles

The hepatitis C viral proteins NS3/4A protease, NS5B polymerase, and NS5A are clinically validated targets for direct-acting antiviral therapies. The NS5B polymerase may be inhibited directly through the action of nucleosides or nucleotide analogues or al

Discovery of GS-9669, a thumb site II non-nucleoside inhibitor of NS5B for the treatment of genotype 1 chronic hepatitis C infection

Investigation of thiophene-2-carboxylic acid HCV NS5B site II inhibitors, guided by measurement of cell culture medium binding, revealed the structure-activity relationships for intrinsic cellular potency. The pharmacokinetic profile was enhanced through incorporation of heterocyclic ethers on the N-alkyl substituent. Hydroxyl groups were incorporated to modulate protein binding. Intrinsic potency was further improved through enantiospecific introduction of an olefin in the N-acyl motif, resulting in the discovery of the phase 2 clinical candidate GS-9669. The unexpected activity of this compound against the clinically relevant NS5B M423T mutant, relative to the wild type, was shown to arise from both the N-alkyl substituent and the N-acyl group.

HETEROCYCLIC COMPOUND

Provided is a compound useful for the prophylaxis or treatment of cancer. The present invention relates to a compound represented by formula (I): wherein each symbol in the formula is as defined in the specification, or a salt thereof or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer.

THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS

The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer

3-CARBONYLAMINOTHIOPHENE-2-CARBOXYLIC ACIDS AS HEPATITIS C VIRUS INHIBITORS

The present invention relates to novel 2-carboxy thiophene compounds of the formula (I): and salts thereof, to pharmaceutical compositions containing them and their use in medicine, as anti-viral agents. Specifically, the present invention relates to comp

Thienopyrimidinone bis-aminopyrrolidine ureas as potent melanin-concentrating hormone receptor-1 (MCH-R1) antagonists

A series of thienopyrimidinone bis-aminopyrrolidine ureas were designed, synthesized, and evaluated for their ability to bind melanin-concentrating hormone receptor-1. These compounds exhibit potent binding affinity (Ki = 3 nM) and good in vitro metabolic stability.

ANTIVIRAL 2-CARBOXY-THIOPHENE COMPOUNDS

Anti-viral agents of compounds of Formula (I) : wherein A, R1, R2 and R3 are as defined in the specification, processes for their preparation and their use in HCV treatment are provided.

Melanin concentrating hormone antagonists

The present invention relates to compounds capable of serving as moderators of human and mammalian appetite and as such provide a means for reducing body mass and controlling obesity.

MELANIN-CONCENTRATING HORMONE RECEPTOR ANTAGONISTS AND COMPOSITIONS AND METHODS RELATED THERETO

Melanin-concentrating hormone (MCH) receptor antagonists are disclosed having utility for the treatment of MCH receptor-based disorders such as obesity. The compounds of this invention have the following structure of formula (I) including pharmaceutically acceptable salts, esters, solvates, stereoisomers, and prodrugs thereof, wherein m, n, Q1, Q2, R1, R2, R3, R4, R7 and X are as defined herein. Also disclosed are compositions containing a compound of this invention, as well as methods relating to the use thereof.