352016-27-4

Upstream product

• 288083-64-7 1-benzyl-6-benzyloxy-7-methoxy-3,4-dihydroisoquinoline 
• 100-44-7 benzyl chloride 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 16575-33-0 N-(3-benzyloxy-4-methoxyphenylethyl)-phenylacetamide 
• 63909-29-5 3-benzyloxy-4-methoxy-β-nitrostyrene 
• 621-59-0 isovanillin 

Downstream Products

• 478855-08-2 (6-benzyloxy-7-methoxy-isoquinolin-1-yl)-phenyl-methanone 

Relevant academic research and scientific papers

Syntheses and antitumor targeting G1 phase of the cell cycle of benzoyldihydroisoquinolines and related 1-substituted isoquinolines

A series of 1-substituted 3,4-dihydroisoquinolines were synthesized and tested in vitro against the leukemia L 1210 cell line to evaluate their ability to perturb the cell cycle by arresting cells in the G1 phase. 1-Benzoylimines, 1-phenylimines, and 1-alkylimines were synthesized. The most powerful cytotoxic derivatives, 1-benzoyl-3,4-dihydroisoquinolines (1-26), were obtained from amides I via 1-benzyl-3,4-dihydroisoquinoline in good yield by a direct selective oxidation of the benzylic carbon of the corresponding imines through 10% Pd/C in acetonitrile. SAR studies let us to identify the essential structural features for cytotoxic activity. The most bioactive compounds (with IC50 5μM) were BzDHIQ (13, 22, 21, 8, 9, 11, 1, 20, 6, and 19), and they are characterized by the following: (i) An α-ketoimine moiety is necessary for potent antiproliferative activity (1-phenyl- and 1-alkyl-3,4-dihydroisoquinoline derivatives, 34-40, are less active). (ii) An hydrophobic, benzyloxy, alkyloxy, or allyloxy group at the C-6 position seems to be relevant for cytotoxicity. (iii) Regarding the influence of the benzoylic moiety, both the unsubstituted (13, 8, 9, 11, 1, and 6) and the 3′-monosubstituted (22, 21, 20, and 19) compounds were more potent than compounds with other substitutions.

An efficient method for the preparation of antitumoral α-keto-imines benzyldihydroisoquinolines by selective benzylic oxidation with C/Pd in acetonitrile

A series of potent antitumor α-keto-imine BDHIQ derivatives were synthesized and assayed in vitro against L1210 leukemia cell line. A new and easy method for the direct formation of α-keto-imine from imine BDHIQ's was performed with 10% C/Pd in acetonitrile.