C-C bond formation at C-2 of a quinoline ring: synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors |
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Authors: | Kumar K Shiva Kiran Kumar S Yogi Sreenivas B Gorja Dhilli Rao Kapavarapu Ravikumar Rambabu D Rama Krishna G Reddy C Malla Basaveswara Rao M V Parsa Kishore V L Pal Manojit |
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Institution: | Institute of Life Sciences, University of Hyderabad Campus, Gachibowli, Hyderabad 500 046, India. |
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Abstract: | A number of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives were synthesized via AlCl(3)-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC(50) ~0.89 μM) is presented. |
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