2,6,9-Triazabicyclo[3.3.1]nonanes as overlooked amino-modification products by acrolein.
The reaction of several primary amines with acrolein smoothly provided the corresponding 2,6,9-triazabicyclo[3.3.1]nonanes through a formal [4 + 4] reaction of the intermediary unsaturated imines. The reactivity profiles in aqueous media and the results from cytotoxic activity assays suggested that the caged products may be relevant in biological systems and may contribute to the mechanisms underlying the oxidative stress response to acrolein.
Biofunctional Synthetic Chemistry Laboratory, RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. kotzenori@riken.jp.
Ayumi
A
Tsutsui
Katsunori
K
Tanaka
D000171:Acrolein / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D053961:Azabicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D018384:Oxidative Stress / Q000187:drug effects; D013329:Structure-Activity Relationship
D000588:Amines; D000970:Antineoplastic Agents; D053961:Azabicyclo Compounds; D000171:Acrolein