Synthesis of Privileged Scaffolds by Using Diversity‐Oriented Synthesis |
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Authors: | Ramu Surakanti Sumalatha Sanivarapu Chiranjeevi Thulluri Pravin S Iyer Raghuram S Tangirala Rambabu Gundla Dr Uma Addepally Y L N Murthy Lakshmi Velide Dr Subhabrata Sen |
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Institution: | 1. Chemistry Services, GVKBioscience, Plot 28?A, IDA Nacharam, Hyderabad (India);2. Department of Chemistry, Food, Drugs and Water, College of Science and Technology, Jawaharlal Andhra University, Vishakhapatnam (India);3. Department of Biotechnology, Gokaraju Rangaraju Institute of Engineering and Technology, Hyderabad (India);4. Institute of Science and Technology, Jawaharlal Nehru Technological University, Kukatpally, Hyderabad (India) |
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Abstract: | An elegant reagent‐controlled strategy has been developed for the generation of a diverse range of biologically active scaffolds from a chiral bicyclic lactam. Reduction of the chiral lactam with LAH or alkylation with LHMDS to trigger different cyclization reactions have been shown to generate privileged scaffolds, such as pyrrolidines, indolines, and cyclotryptamines. Their amenability to substitution allows us to create various compound libraries by using these scaffolds. In silico studies were used to estimate the drug‐like properties of these compounds. Selected compounds were subjected to anticancer screening by using three different cell lines. In addition, all these compounds were subjected to antibacterial screening to gauge the spectrum of biological activity that was conferred by our DOS methodology. Gratifyingly, with no additional iterative cycles, our method directly generated anticancer compounds with potency at low nanomolar concentrations, as represented by spiroindoline 14 . |
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Keywords: | biological activity diversity‐oriented synthesis heterocycles scaffolds spiro compounds |
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