121746-08-5

Upstream product

• 4651-91-6 3-cyano-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene 
• 532-55-8 Benzoyl isothiocyanate 
• 108-94-1 cyclohexanone 
• 98-88-4 benzoyl chloride 

Downstream Products

• 121746-14-3 2-(methylsulfanyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4-amine 
• 382609-52-1 (4-imino-2-mercapto-4,5,6,7-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-3(4H)-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Synthesis, cytotoxicity and toxicity of thieno[2,3-d]pyrimidine derivatives derived from 2-amino-3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophene

The 4,5,6,7-tetrahydrobenzo[b]thiophene derivative 1 reacted with benzoylisothiocyanate to give N-benzoylthiourea derivative 3. The latter underwent ready cyclization to give the tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine derivative 4 which was used as t

Structure-Guided Optimization of Inhibitors of Acetyltransferase Eis from Mycobacterium tuberculosis

The enhanced intracellular survival (Eis) protein of Mycobacterium tuberculosis (Mtb) is a versatile acetyltransferase that multiacetylates aminoglycoside antibiotics abolishing their binding to the bacterial ribosome. When overexpressed as a result of promoter mutations, Eis causes drug resistance. In an attempt to overcome the Eis-mediated kanamycin resistance of Mtb, we designed and optimized structurally unique thieno[2,3-d]pyrimidine Eis inhibitors toward effective kanamycin adjuvant combination therapy. We obtained 12 crystal structures of enzyme-inhibitor complexes, which guided our rational structure-based design of 72 thieno[2,3-d]pyrimidine analogues divided into three families. We evaluated the potency of these inhibitors in vitro as well as their ability to restore the activity of kanamycin in a resistant strain of Mtb, in which Eis was upregulated. Furthermore, we evaluated the metabolic stability of 11 compounds in vitro. This study showcases how structural information can guide Eis inhibitor design.

Antiarrhythmic, serotonin antagonist and antianxiety activities of novel substituted thiophene derivatives synthesized from 2-amino-4,5,6,7-tetrahydro-N- phenylbenzo[b]thiophene-3-carboxamide

A series of novel thiophene derivatives 3-17 were synthesized by initial reactions of 2-amino-4,5,6,7-tetrahydro-N-phenylbenzo[b]thiophene-3-carboxamide 1 and 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile 7 with different organic reagents. T

2-(Benzoylimino)thiazolidin-4-ones: Formation by an alternative ring closure and analysis of rotational barriers

The reactions of N-benzoyl-N'-(o-cyanoaryl)thioureas with ethyl bromoacetate under alkaline conditions led to the formation of either fused 2-(alkylsulfanyl)-4-aminopyrimidines or 2-(benzoylimino)-3-(o-cyanoaryl) thiazolidin-4-ones. The accurate applicati

Analogs of a 4-aminothieno[2,3-d]pyrimidine lead (QB13) as modulators of P-glycoprotein substrate specificity

P-glycoprotein (P-gp) is an important factor in the development of multidrug resistance (MDR) in cancer cells. In literature reports, a thieno[2,3-d]pyrimidine (QB13) was described as P-gp modulator and opposed effects on the cell accumulation of distinct

A Facile Synthesis of 2-Alkylthio-4-amino-thienopyrimidines

The reaction of 2-benzoylthioureidothiophene-3-carbonitriles D/8,9 with diluted NaOH yields 4-amino-thienopyrimidin-2(1H)-thiones E/10,11.Compounds D react in alkaline solution with various alkyl halides in one step to give 2-alkylthio-4-amino-thie