Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines was written by Salem, Mohamed S. H.;Abdel Aziz, Yasmine M.;Elgawish, Mohamed S.;Said, Mohamed M.;Abouzid, Khaled A. M.. And the article was included in Bioorganic Chemistry in 2020.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:
In this study, twenty eight new compounds based on thieno[2,3-d]pyrimidine scaffold I [R = (2-methylphenyl)aminyl, diphenylaminyl, 2-naphthyloxy, etc.] and II [X = O, S; R1 = Ph, 4-fluorophenyl, ethyl] were synthesized as anti-pancreatic cancer agents mimicking the benzofuro[3,2-d]pyrimidine derivative, amuvatinib. Various linkers including amides, esters, ketones, urea and thiourea derivatives were utilized to study their effect on the anti-proliferative activity of these compounds Most of the tested compounds revealed good cytotoxic activities against pancreatic carcinoma cell line PANC-1. Compound I [R = (4-chlorophenyl)aminyl] (A) showed the highest cytotoxicity with an IC50 value of 5.4μM. Furthermore, (A) showed excellent platelet derived growth factor receptor (PDGFR-α) inhibitory activity, with IC50 value 0.155μM. Docking study was carried out into PDGFR-α active site which showed comparable binding mode to that of FDA approved PDGFR-α inhibitor, imatinib. 3D-Quant. structure activity relationship (QSAR) model was built up with five-featured pharmacophore which could be implemented for emerging effective lead structures. These compounds could serve as a new chemotype for discovering new agents for pancreatic cancer therapy. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).
2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Safety of 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts