Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies |
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| Authors: | Nagula Markandeya Nagula Shankaraiah Ch Sanjeeva Reddy Leonardo Silva Santos Ahmed Kamal |
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| Institution: | 1. Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500 607, India;2. Department of Chemistry, Kakatiya University, Warangal 506 009, India;3. National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037, India;4. Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, University of Talca, Talca, PO Box 747, Chile |
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| Abstract: | 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. |
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