Enterovirus inhibitory activity of C-8-tert-butyl substituted 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones was written by Kumar Biswas, Bishyajit;Malpani, Yashwardhan R.;Ha, Neul;Kwon, Do-Hyun;Shin, Jin Soo;Kim, Hae-Soo;Kim, Chonsaeng;Han, Soo Bong;Lee, Chong-Kyo;Jung, Young-Sik. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2017.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate The following contents are mentioned in the article:
Members of a series of 4-aryl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-ones were prepared and tested against representative enteroviruses including Human Coxsackievirus B1 (Cox B1), Human Coxsackievirus B3 (Cox B3), human Poliovirus 3 (PV3), human Rhinovirus 14 (HRV14), human Rhinovirus 21 (HRV21) and human Rhinovirus 71 (HRV71). The C-8-tert-Bu group on the tetrahydrobenzene ring in these substances is crucial for their enterovirus activity. One member of this group, 8-(tert-butyl)-4-phenyl-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3-a]pyrimidin-5(4H)-one , showed single digit micromolar activities (1.6-8.85 μM) against a spectrum of viruses screened, and the highest selectivity index (SI) values for Cox B1 (>11.2), for Cox B3 (>11.5), and for PV3 (>51.2), resp. In contrast, 8-(tert-butyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3a]pyrimidin-5(4H)-one, was the most active analog against the selected HRVs (1.8-2.6 μM), and showed the highest selectivity indexes among the group of compounds tested. The SI values for 8-(tert-butyl)-4-(4-methoxyphenyl)-6,7,8,9-tetrahydrobenzo[4,5]thieno[3,2-e][1,2,4]triazolo[4,3a]pyrimidin-5(4H)-one were 11.5 for HRV14, 8.4 for HRV21, and 12.1 for HRV71, resp. This study involved multiple reactions and reactants, such as Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate).
Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (cas: 95211-67-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Safety of Ethyl 2-amino-4-methyl-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate
Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem