24237-37-4

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-6-BENZYL-4,5,6,7-TETRAHYDRO-THIENO[2,3-C]PYRIDINE-3-CARBONITRILE is used as a potential pharmaceutical agent for its possible anti-cancer, anti-inflammatory, or antimicrobial properties. Its unique structure and functional groups make it a target for synthetic organic chemistry and drug discovery.
However, it is important to note that the specific applications and reasons for using 2-AMINO-6-BENZYL-4,5,6,7-TETRAHYDRO-THIENO[2,3-C]PYRIDINE-3-CARBONITRILE in the pharmaceutical industry are not explicitly provided in the materials. Further studies and research are required to fully understand its chemical and biological properties and to determine its exact applications and benefits in this field.

Upstream product

• 3612-20-2 1-phenylmethyl-4-piperidone 
• 109-77-3 malononitrile 

Downstream Products

• 37071-32-2 5,6,7,8-tetrahydro-7-(benzyl)-pyrido[4',3':4,5]thieno[2,3-D]pyrimidin-2,4-diamine 
• 331457-91-1 N-benzoyl-N'-(6-benzyl-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)thiourea 
• 126834-61-5 7-benzyl-4-amino-5,6,7,8-tetrahydro-pyrido[4',5':4,5]thieno[2,3-d]pyrimidine 

Relevant academic research and scientific papers

2-Substituted thienotetrahydropyridine derivatives: Allosteric ectonucleotidase inhibitors

The antithrombotic prodrugs ticlopidine and clopidogrel are thienotetrahydro-pyridine derivatives that are metabolized in the liver to produce thiols that irreversibly block adenosine diphosphate (ADP)-activated P2Y12 receptors on thrombocytes. In their native, nonmetabolized form, both drugs were reported to act as inhibitors of ectonucleoside triphosphate diphosphohydrolase-1 (NTPDase1, CD39). CD39 catalyzes the extracellular hydrolysis of nucleoside tri- and diphosphates, mainly adenosine 5?-triphosphate (ATP) and ADP, yielding adenosine monophosphate, which is further hydrolyzed by ecto-5?-nucleotidase (CD73) to produce adenosine. While ATP has proinflammatory effects, adenosine is a potent anti-inflammatory, immunosuppressive agent. Inhibitors of CD39 and CD73 have potential as novel checkpoint inhibitors for the immunotherapy of cancer and infection. In the present study, we investigated 2-substituted thienotetrahydropyridine derivatives, structurally related to ticlopidine, as CD39 inhibitors. Due to their substituent on the 2-position, they will not be metabolically transformed into reactive thiols and can, therefore, be expected to be devoid of P2Y12 receptor-antagonistic activity in vivo. Several of the investigated 2-substituted thienotetrahydropyridine derivatives showed concentration-dependent inhibition of CD39. The most potent derivative, 32, showed similar CD39-inhibitory potency to ticlopidine, both acting as allosteric inhibitors. Compound 32 showed an improved selectivity profile: While ticlopidine blocked several NTPDase isoenzymes, 32 was characterized as a novel dual inhibitor of CD39 and CD73.

Basic Ionic Liquid [bmIm]OH-Mediated Gewald Reaction as Green Protocol for the Synthesis of 2-Aminothiophenes

A simple, efficient, and environmental friendly procedure was developed based on the Gewald reaction for the synthesis of 2-aminothiophenes using a basic ionic liquid [bmIm]OH as both catalyst and solvent. Besides being a green protocol, the method offers advantages of successful synthesis of a variety of alkyl, aryl, alkoxy, and alkylamino-2-aminothiophenes in good yields.

3- and 6-Substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as A1 adenosine receptor allosteric modulators and antagonists

A series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were prepared and evaluated as potential allosteric modulators at the A1 adenosine receptor. The structure-activity relationships of the 3- and 6-positions of a series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were explored. Despite finding that 3- and 6-substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines possess the ability to recognize an allosteric site on the agonist-occupied A1AR at relatively high concentrations, the structural modifications we have performed on this scaffold favor the expression of orthosteric antagonist properties over allosteric properties. This research has identified 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as novel class of orthosteric antagonist of the A1AR and highlighted the close relationship between structural elements governing allosteric modulation and orthosteric antagonism of agonist function at the A1AR.