190579-92-1

Upstream product

• 7357-70-2 Cyanothioacetamide 
• 34772-98-0 (2E)-3-(dimethylamino)-1-thien-2-ylprop-2-en-1-one 
• 34772-98-0 3-dimethylamino-1-thiophen-2-ylpropenone 
• 88-15-3 2-Acetylthiophene 
• 50-00-0 formaldehyd 

Downstream Products

• 213481-48-2 2-(2-Nitro-benzylsulfanyl)-6-thiophen-2-yl-nicotinonitrile 
• 339022-03-6 2-(2-Oxo-2-phenyl-ethylsulfanyl)-6-thiophen-2-yl-nicotinonitrile 
• 933853-60-2 2-[2-(3-methoxy-phenyl)-2-oxo-ethylsulfanyl]-6-thiophen-2-yl-nicotinonitrile 
• 933973-25-2 2-[2-(4-bromo-phenyl)-2-oxo-ethylsulfanyl]-6-thiophen-2-yl-nicotinonitrile 
• 313380-32-4 2-(cyanomethylthio)-6-(2-thienyl)pyridine-3-carbonitrile 

Relevant academic research and scientific papers

Discovery and structure-activity relationships study of thieno[2,3-b]pyridine analogues as hepatic gluconeogenesis inhibitors

Type 2 diabetes mellitus (T2DM) is a chronic, complex and multifactorial metabolic disorder, and targeting gluconeogenesis inhibition is a promising strategy for anti-diabetic drug discovery. This study discovered a new class of thieno[2,3-b]pyridine derivatives as hepatic gluconeogenesis inhibitors. First, a hit compound (DMT: IC50 = 33.8 μM) characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. Structure activity relationships (SARs) study showed that replaced the CF3 in the thienopyridine core could improve the potency and led to the discovery of 8e (IC50 = 16.8 μM) and 9d (IC50 = 12.3 μM) with potent inhibition of hepatic glucose production and good drug-like properties. Furthermore, the mechanism of 8e for the inhibition of hepatic glucose production was also identified, which could be effective through the reductive expression of the mRNA transcription level of gluconeogenic genes, including glucose-6-phosphatase (G6Pase) and hepatic phosphoenolpyruvate carboxykinase (PEPCK). Additionally, 8e could also reduce the fasting blood glucose and improve the oral glucose tolerance and pyruvate tolerance in db/db mice. The optimization of this class of derivatives had provided us a start point to develop new anti-hepatic gluconeogenesis agents.

3-Amino-thieno[2,3-b]pyridines as microtubule-destabilising agents: Molecular modelling and biological evaluation in the sea urchin embryo and human cancer cells

A series of 3-amino-thieno[2,3-b]pyridines was prepared and tested in a phenotypic sea urchin embryo assay to identify potent and specific molecules that affect tubulin dynamics. The most active compounds featured a tricyclic core ring system with a fused cycloheptyl or cyclohexyl substituent and unsubstituted or alkyl-substituted phenyl moiety tethered via a carboxamide. Low nano-molar potency was observed in the sea urchin embryos for the most active compounds (1–5) suggestive of a microtubule-destabilising effect. The molecular modelling studies indicated that the tubulin colchicine site is inhibited, which often leads to microtubule-destabilisation in line with the sea urchin embryo results. Finally, the identified hits displayed a robust growth inhibition (GI50of 50–250?nM) of multidrug-resistant melanoma MDA-MB-435 and breast MDA-MB-468 human cancer cell lines. This work demonstrates that for the thieno[2,3-b]pyridines the most effective mechanism of action is microtubule-destabilisation initiated by binding to the colchicine pocket.

Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.

Synthesis and docking studies of some 3-amino-6-(thiophen-2-yl)thieno[2,3- b]pyridine derivatives

Some 3-amino-6-(thiophen-2-yl)thieno[2,3-b]pyridine derivatives (4a-j) were synthesized and characterized by 1H NMR, 13C NMR and elemental microanalyses based on the hit compound DZ9202, a nicotinate mononucleotide adenylyltransferase inhibitor against Bacillus anthracis. In the next step, molecular modeling and relative potency of these structures were studied. Copyright

Reactions with hydrazonoyl halides 45: Synthesis of some new triazolino [4,3-a]pyrimidines, pyrazolo [3,4-d]pyridazines, isoxazolo[3,4-d]pyridazines, and thieno[2,3-b]pyridines

Triazolino[4,3-α]pyrimidines pyrazolo[3,4-d]pyridazines and isoxazolo[3,4-d] pyridazines were synthesized from hydrazonoyl halides. Also, 3-aminothieno[2,3-b] pyridines and pyrimidino[4′,5′:4,5]thieno[2,3- b]pyridines were synthesized from cynothioacetamide. Structures of the newly synthesized compounds were established on the basis of elemental analyses and spectral data. Copyright Taylor & Francis LLC.

Thienopyridine and benzofuran derivatives as potent anti-tumor agents possessing different structure-activity relationships

(3-Amino-6-thiophen-2-yl-thieno[2,3-b]pyridin-2-yl)phenylmethanone (3) was discovered as a new type of cytotoxic agent selective against a tumorigenic cell line. The molecular structure of a previously reported compound, (4-hydroxy-3-methyl-6-phenylbenzofuran-2-yl)phenylmethanone (2), had remarkably similar bioisosteric substructures to that of compound 3. Although the relationship between the molecular structure and biological activity of each derivative synthesized from these two hit compounds (2 and 3) were studied, unexpectedly no correlation was observed. However, after further synthetic study from 3, one of the most potent derivative (10k) having a different SAR profile from 2, was discovered.

Regioselective synthesis and properties of 3-cyano-6-thienylpyridine-2(1H)-thiones

Reactions of sodium derivatives of 2-and 3-thenoylacetaldehydes with cyanothioacetamide gave 2-and 3-cyano-6-thienylpyridine-2(1H)-thiones, which were used in the synthesis of substituted 2-alkylthiopyridines, thieno[2,3-b]pyridines, and other fused heterocycles.