165558-79-2Relevant academic research and scientific papers
Preparation of benzindole compounds from naphthalene compounds
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, (2008/06/13)
The invention relates to a process for preparing a substituted 2-amino-benz[cd]indole of the Formula I: STR1 The nitro group of a substituted 1-nitro-8-cyano-naphthalene compound is reduced to an amine group to form a substituted 1-amino-8-cyano-naphthalene compound, which is cyclized to form the substituted 2-amino-benz[cd]indole. The reduction and cyclization may be effected in a one-pot procedure using a reducing agent such as stannous chloride, which generates an acid that cyclizes the reduction product. The syntheses of the 1-nitro-8-cyanonaphthalene compound and its precursors are also described.
Synthesis and Biological Evaluation of Novel 2,6-Diaminobenzindole Inhibitors of Thymidylate Synthase Using the Protein Structure as a Guide
Varney, Michael D.,Palmer, Cindy L.,Deal, Judith G.,Webber, Stephanie,Welsh, Katherine M.,et al.
, p. 1892 - 1903 (2007/10/02)
The design, synthesis, and biochemical and biological evaluations of a novel series of 2,6-diaminobenzindole-containing inhibitors of human thymidylate synthase (TS) are described.The compounds are characterized by having either a pyridine or pyridazine ring in place of the (phenylsulfonyl)morpholinyl group of the known inhibitor N6--N6-methyl-2,6-diaminobenzindole glucuronate (i).Active compounds from this series showed human TS inhibition constants below the 10 nM level and were potent, selective submicromolar antitumor agents in cell culture.The compounds were synthesized by reductive alkylation of a substituted 6-aminobenzindole or reductive cyclization of a substituted 1-cyano-8-nitronaphthalene.
