1263193-96-9Relevant academic research and scientific papers
Asymmetric syntheses of piperidino-benzodiazepines through 'cation-pool' host/guest supramolecular approach and their DNA-binding studies
Markandeya, Nagula,Shankaraiah, Nagula,Reddy, Ch. Sanjeeva,Santos, Leonardo Silva,Kamal, Ahmed
experimental part, p. 2625 - 2630 (2011/02/16)
The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed. The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position. This procedure features the use of a 'cation-pool' strategy and also a host/guest supramolecular co-catalysis approach. In this study, the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation, which are followed by nucleophilic addition to an N-acyliminium ion. In addition, intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a,b and 5a,b. Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81.
