18678-14-3

Usage

Uses

Used in Pharmaceutical Industry:
2-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL is used as a therapeutic agent for the treatment of diabetes and obesity. It functions as an inhibitor of protein tyrosine phosphatase 1B (PTP-1B), which is crucial in insulin signaling and the regulation of glucose and lipid metabolism. By inhibiting PTP-1B, 2-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL can enhance insulin sensitivity and reduce blood glucose levels, offering a potential solution for managing diabetes and obesity.
Used in Drug Development:
2-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL is used as a lead compound in the development of new anti-diabetic and anti-obesity drugs. Its unique molecular structure, featuring a phenyl group and a thieno-pyrimidine ring, provides a distinct target for medicinal chemistry efforts, allowing for the design and synthesis of novel inhibitors with improved potency, selectivity, and pharmacokinetic properties.
Used in Research:
2-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL is used as a research tool to study the role of protein tyrosine phosphatase 1B (PTP-1B) in insulin signaling and glucose homeostasis. By investigating the effects of 2-PHENYLTHIENO[3,2-D]PYRIMIDIN-4-OL on PTP-1B activity and its downstream consequences, researchers can gain insights into the molecular mechanisms underlying insulin resistance and develop strategies for the treatment of diabetes and obesity.

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 825-60-5 benzimidic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 79128-70-4 methyl 3-benzoylaminothiophene-2-carboxylate 
• 100-42-5 styrene 
• 147123-47-5 3-aminothiophene-2-carboxamide 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 299199-50-1 N-(quinolin-8-yl)thiophene-2-carboxamide 
• 1670-14-0 benzamidine monohydrochloride 
• 618-32-6 Benzoyl bromide 
• 108-88-3 toluene 

Downstream Products

• 214417-22-8 4-chloro-2-phenylthieno[3,2-d]pyrimidine 

Relevant academic research and scientific papers

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

Chemical Space Exploration around Thieno[3,2- d]pyrimidin-4(3 H)-one Scaffold Led to a Novel Class of Highly Active Clostridium difficile Inhibitors

Clostridium difficile infection (CDI) is the leading cause of healthcare-associated infection in the United States. Therefore, development of novel treatments for CDI is a high priority. Toward this goal, we began in vitro screening of a structurally diverse in-house library of 67 compounds against two pathogenic C. difficile strains (ATCC BAA 1870 and ATCC 43255), which yielded a hit compound, 2-methyl-8-nitroquinazolin-4(3H)-one (2) with moderate potency (MIC = 312/156 μM). Optimization of 2 gave lead compound 6a (2-methyl-7-nitrothieno[3,2-d]pyrimidin-4(3H)-one) with improved potency (MIC = 19/38 μM), selectivity over normal gut microflora, CC50s > 606 μM against mammalian cell lines, and acceptable stability in simulated gastric and intestinal fluid. Further optimization of 6a at C2-, N3-, C4-, and C7-positions resulted in a library of >50 compounds with MICs ranging from 3 to 800 μM against clinical isolates of C. difficile. Compound 8f (MIC = 3/6 μM) was identified as a promising lead for further optimization.

Copper-mediated synthesis of quinazolin-4(3: H)-ones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides

An efficient copper-mediated tandem C(sp2)-H amination to provide quinazolinones from N-(quinolin-8-yl)benzamide and amidine hydrochlorides has been developed. It can afford rather complex products in a single step synthesis from easily availab

Method for synthesizing 2-heterocyclic benzene (2,3-d) pyrimidine-4(3H)-ketone compounds

The invention discloses a method for synthesizing 2-heterocyclic benzene (2,3-d) pyrimidine-4(3H)-ketone compounds. Carbon bond rupture of styrene compound carbon is utilized to generate benzaldehydecompounds, the generated benzaldehyde compounds and heterocyclic o-amino-formamide compounds are subjected to intermolecular condensation coupling reaction to obtain the 2-heterocyclic benzene (2,3-d)pyrimidine-4(3H)-ketone compounds, wherein the styrene compounds refer to styrene or 2-ethoxystyrene, and the heterocyclic o-amino-formamide compounds refer to 3-aminothiophene-2-formamide or 4-amino-1-methyl-3-n-propyl-1H-pyrazol-5-formamide. The method has the advantages that raw materials are easy to obtain, and more economy is achieved; efficient reaction and high yield are achieved; high temperature and high pressure are not needed, and reaction conditions are moderate; the synthesis process is easy to operate, and the obtained product is easy for post-processing and suitable for large scale production.

Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives

A series of thieno[2,3-d]- and thieno[3,2-d]pyrimidines have been easily synthesized using as key step a deproto-cadmiation-trapping sequence. Some of the compounds thus synthesized were screened for anticancer (cytotoxic) activities, and (S)-2-(6-iodo-2-

Design, synthesis, and biological activities of new thieno[3,2- d]pyrimidines as selective type 4 phosphodiesterase inhibitors

A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (c