New cyrhetrenyl and ferrocenyl sulfonamides: Synthesis, characterization, X-ray crystallography, theoretical study and anti-Mycobacterium tuberculosis activity. (25th September 2017)

• Record Type: Journal Article
• Authors: Quintana, Cristóbal; Silva, Gisella; Klahn, A. Hugo; Artigas, Vania; Fuentealba, Mauricio; Biot, Christophe; Halloum, Iman; Kremer, Laurent; Novoa, Néstor; Arancibia, Rodrigo
• Is Part Of: Polyhedron. Volume 134(2017)
• Page Start: 166
• Page End: 172
• Publication Date: 2017-09-25
• Subjects: Organometallic sulfonamide -- Cyrhetrene -- Ferrocene -- Anti-Mycobacterium tuberculosis activity -- DFT calculations; Chemistry, Inorganic -- Periodicals; Chimie inorganique -- Périodiques; Organometaalverbindingen; Anorganische chemie; 546.05
• DOI: 10.1016/j.poly.2017.06.015
• Languages: English
• ISSNs: 0277-5387

Abstract

Graphical abstract: A new series of cyrhetrenyl and ferrocenyl sulfonamides were have been synthesized and characterized by spectroscopy and X-ray crystallography. DFT studies were carried out to rationalize the influences of the electronic natures of the organometallic fragments into the sulfonamide skeleton. All the complexes were screened in vitro against Mycobacterium tuberculosis and exhibited only modest activities in the micromolar range. Abstract: A new series of cyrhetrenyl and ferrocenyl sulfonamides were designed, synthesized and characterized. The reactions of organometallic amines (P2 andP3 ) with the corresponding arylsulfonyl chlorides produced cyrhetrenyl (2a-c ) and ferrocenyl (3a-c ) sulfonamide derivatives. All the compounds were characterized by conventional spectroscopic techniques (FT-IR, 1 H and 13 C NMR and mass spectrometry). The proposed molecular structures of2a and3a were confirmed by single-crystal X-ray crystallography. Theoretical calculations at the DFT level were also carried out as an approximation to rationalize the influences of the electronic natures of the organometallic fragments into the sulfonamide skeleton. All the complexes were screened in vitro against Mycobacterium tuberculosis and exhibited only modest activities in the micromolar range.