New thieno[2,3-b]pyridine phosphoramidates compounds were synthesized and characterized by infrared; 1H, 13C, and 31P NMR spectroscopy; and high-resolution mass spectrometry. The products were obtained in good yields (64-82%) under mild conditions by nucleophilic aromatic substitution reaction of aminoalkylphosphoramidates over 4-chlorothieno[2,3-b] pyridine-5-carbonitrile. The crystal structures of two compounds were solved by X-ray diffraction and showed a network of intermolecular interactions involving phosphoramidate groups. Druglike properties and toxicity of the new compounds were studied with the help of the software Molinspiration, Osiris, and Toxtree, and were compared with the standard drugs amphotericin B, miltefosine, benznidazole, and nifurtimox. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] © 2013 Copyright Taylor and Francis Group, LLC.
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