304463-94-3Relevant academic research and scientific papers
Design, synthesis, and inhibition of platelet aggregation for some 1-o-chlorophenyl-1,2,3,4-tetrahydroisoquinoline derivatives
Yang, Jie,Hua, Wei-Yi,Wang, Fu-Xiang,Wang, Zhi-Yuan,Wang, Xiang
, p. 6547 - 6557 (2007/10/03)
Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent), which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Based on ticlopidine active as an ADP receptor antagonist for inhibiting platelet aggregation in clinical test, and upon finding (±)-1,2-substituted-7-sulfonylamide/amide-1,2,3,4-tetrahydroisoquinoline (11-31) inhibited of platelet aggregation, a series of (±)-1-o- chlorophenyl-2-substituted-tetrahydroisoquinoline derivatives was designed and synthesized. Four analogs proved to be potential antiplatelet aggregation agents, and compound 9 (TQP-3, applying for patent) which inhibits ADP-induced human platelet aggregation with IC50 values of approximately 0.206 nM was the most active. Compound 2 is more active than compound 1, which (Type I) is similar to ticlopidine. This is because there is a spacial hindrance in compound 1, and the o-chloro group of compound 2 may play the same a role as o-chloro group of ticlopidine. On the other hand, with the different substitutions at different positions on the 2-substituted phenylacyl group, their inhibition of platelet aggregation differs. These compounds with m-substituted group (5, 7, 9) showed a higher IC50 value for inhibiting ADP-induced human platelet aggregation than those with o-substituted group (4, 6) or p-substituted group (3, 8). It was observed that their inhibition is bromine-substituted derivative (9), chlorine-substituted derivative (7), and nitro-substituted derivative (5) in turn. Moreover, these compounds (Type II) may be more similar to clopidogrel than to ticlopidine due to the acyl group at 2 position of the nucleus playing a role as the ester group of clopidogrel. It was conjectured that these analogs function as a potential antiplatelet aggregation role by acting as ADP receptor antagonists.
Synthesis of racemic 1,2,3,4-tetrahydroisoquinolines and their resolution
Suna,Trapencieris
, p. 287 - 300 (2007/10/03)
1-Aniline-substituted 3,4-dihydroisoquinolines were obtained in various ways using the Bischler-Napieralski reaction. The effect of the protecting group at the aniline nitrogen atom on the course of the reaction has been studied and it was found that the N-phthalyl group was stable under the cyclization conditions. The dihydroisoquinolines were reduced to the racemic 1,2,3,4-tetrahydroisoquinolines which were resolved by crystallization of the diastereomeric tartrates. Two examples of 1,2,3, 4-tetrahydroisoquinolines were obtained in optically pure form (>99% ee).
