Organometallic tosyl hydrazones: Synthesis, characterization, crystal structures and in vitro evaluation for anti-Mycobacterium tuberculosis and antiproliferative activities. (27th July 2017)

• Record Type: Journal Article
• Authors: Concha, Camila; Quintana, Cristóbal; Klahn, A. Hugo; Artigas, Vania; Fuentealba, Mauricio; Biot, Christophe; Halloum, Iman; Kremer, Laurent; López, Rodrigo; Romanos, Javier; Huentupil, Yosselin; Arancibia, Rodrigo
• Is Part Of: Polyhedron. Volume 131(2017)
• Page Start: 40
• Page End: 45
• Publication Date: 2017-07-27
• Subjects: Organometallic tosyl hydrazones -- Cyrhetrene -- Cymantrene -- Tuberculosis -- Cancer; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2017.04.031
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: A new series of organometallic tosyl hydrazones were synthesized and characterized by spectroscopy and X-ray crystallography. All compounds were evaluated in vitro against M. tuberculosis and non-small cell lung cancer cells. The bioorganometallic compounds showed poor antitubercular activity. The antitumoral evaluation demonstrated that the electronic effects of the substituents on the hydrazone carbon are influencing factor in the anticancer activity. Abstract: A series of new organometallic tosyl hydrazones of the general formula [{(η 5 -C5 H4 )-C(R) = NNHSO2 C6 H4 CH3 }]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, 1 H and 13 C NMR, mass spectrometry and elemental analysis). In addition, the molecular structures of the cymantrenyl hydrazones2a and2b have been determined by single-crystal X-ray diffraction. In the solid state, both compounds showed an E -configuration around the CN moiety. Evaluation of antitubercular activity, measured in vitro against Mycobacterium tuberculosis mc 2 6230 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 hydrazones1 –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.