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The present work emphasizes the utility of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine as starting precursors. The reaction of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine with a variety of aliphatic and aromatic amines yielded 2‐amino substituted 2,4‐dichlorobenzo[h]naphthyridines. All the compounds were examined for their in vitro anticancer activity against six human cancer lines and docked with PDK1 inhibitors. The structure‐activity relationship studies are revealed that the compounds holding aminocarbazole moiety and triazole amine moiety improve the activity profile. All the structures of synthesized compounds were optimized at B3LYP‐D3/6‐31G(d) level in the water. Furthermore, the electronic properties and biological reactivity of the synthesized compounds are explored using computational techniques.

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