Schakel, Laura; Mirza, Salahuddin; Pietsch, Markus; Lee, Sang-Yong; Keuler, Tim; Sylvester, Katharina; Pelletier, Julie; Sevigny, Jean; Pillaiyar, Thanigaimalai; Namasivayam, Vigneshwaran; Guetschow, Michael; Mueller, Christa E. published an article about the compound: tert-Butyl 2-cyanoacetate( cas:1116-98-9,SMILESS:O=C(OC(C)(C)C)CC#N ).Quality Control of tert-Butyl 2-cyanoacetate. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1116-98-9) through the article.
The antithrombotic prodrugs ticlopidine and clopidogrel are thienotetrahydro-pyridine derivatives that are metabolized in the liver to produce thiols that irreversibly block ADP (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 ATP (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.
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Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem