Amberlite IR-120H catalyzed MCR: design, synthesis and crystal structure analysis of 1,8-dioxodecahydroacridines as potential inhibitors of sirtuins.

Ali Nakhi, P T V A Srinivas, Md Shafiqur Rahman, Ravada Kishore, G P K Seerapu, K Lalith Kumar, Devyani Haldar, M V Basaveswara Rao, Manojit Pal

Dr. Reddy's Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India.

Bioorganic & medicinal chemistry letters 2013 Mar 15

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A rapid, inexpensive and high yielding method has been developed for the synthesis of 1,8-dioxodecahydroacridines using Amberlite IR-120H as a reusable catalyst under open air. These compounds were designed as potential inhibitors of sirtuins and prepared via the MCR of 5,5-dimethyl-1,3-cyclohexanedione, (hetero)aryl aldehydes and (hetero)aromatic amines under mild conditions. Further structure elaboration of a representative compound was performed via Pd catalyzed C-C bond forming reactions. The crystal structure analysis and H-bonding patterns along with in vitro inhibitory activity against yeast Sir2 of the same compound is presented. Docking studies indicated that the compound interacts well with the yeast Sir2. Copyright © 2013 Elsevier Ltd. All rights reserved.

Citation

Ali Nakhi, P T V A Srinivas, Md Shafiqur Rahman, Ravada Kishore, G P K Seerapu, K Lalith Kumar, Devyani Haldar, M V Basaveswara Rao, Manojit Pal. Amberlite IR-120H catalyzed MCR: design, synthesis and crystal structure analysis of 1,8-dioxodecahydroacridines as potential inhibitors of sirtuins. Bioorganic & medicinal chemistry letters. 2013 Mar 15;23(6):1828-33