Organometallic tosyl hydrazones: Synthesis, characterization, crystal structures and in vitro evaluation for anti- Mycobacterium tuberculosis and antiproliferative activities

• DOI: 10.1016/j.poly.2017.04.031
• Publication Date: 2017-04-27T21:45:19Z
• Authors: Camila Concha; Cristóbal Quintana; A. Hugo Klahn; Vania Artigas; Mauricio Fuentealba; Christophe Biot; Iman Halloum; Laurent Kremer; Rodrigo López; Javier Romanos; Yosselin Huentupil; Rodrigo Arancibia
• Keywords: Tosyl; Hydrazone; Moiety

Abstract A series of new organometallic tosyl hydrazones of the general formula [{(η5-C5H4)-C(R) = NNHSO2C6H4CH3}]M(CO)3 (M = Re, Mn; R = H, CH3) were prepared by the reaction between formyl or acetyl organometallic precursors with p-toluenesulfonyl hydrazide. All compounds were characterized by conventional spectroscopic techniques (infrared, 1H and 13C NMR, mass spectrometry and elemental analysis). In addition, the molecular structures of the cymantrenyl hydrazones 2a and 2b have been determined by single-crystal X-ray diffraction. In the solid state, both compounds showed an E-configuration around the C N moiety. Evaluation of antitubercular activity, measured in vitro against Mycobacterium tuberculosis mc26230 strain, indicate that all organometallic tosyl hydrazones are considerably less active than the reference drug isoniazid. The antiproliferative activity against non-small cell lung cancer cells (H1299 cells) was also evaluated. Even though the IC50 measured for hydrazones 1–3 resulted 2–3-fold higher than cisplatin, biological results demonstrate that the electronic effects of the substituents on the hydrazone carbon are influencing factor in the anticancer activity.