VT-NMR and cytotoxic evaluation of some new ortho-(alkylchalcogen)acetanilides |
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Authors: | Susana S. Ramos Sandra S. Almeida Paula M. Leite Renato E.F. Boto Samuel Silvestre Paulo Almeida |
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Affiliation: | 1. UMTP-UBI, Unit of Textile and Paper Materials, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal;2. CICS-UBI—Health Sciences Research Centre, University of Beira Interior, Av. Infante D. Henrique, 6200-506 Covilhã, Portugal;3. Department of Chemistry, University of Beira Interior, Rua Marquês d’Ávila e Bolama, 6201-001 Covilhã, Portugal |
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Abstract: | Several novel atropisomeric N-alkyl-N-[(2-alkylchalcogen)phenyl)]acetamides have been synthesized and fully characterized by 1H and 13C NMR, FTIR, and HRMS (FAB). The barriers of the restricted rotation about the N-aryl bond between the two atropisomeric forms were measured by accurate lineshape simulation of variable temperature NMR (VT-NMR) spectra obtained in DMSO-d6 solution and ranged from 17.0 to 20.5 kcal/mol. The relationship between the structure of the different acetanilide moieties and both coalescence temperature and energy of rotation are herein discussed. Taking in mind the acetamide structural resemblances with nimesulide related compounds known by their anticancer activity, the in vitro cytotoxicity of 20 representative acetanilides, against human breast (MCF-7) and prostate (LNCaP) cancer cell lines as well as normal human dermal fibroblasts (NHDF) was also preliminary evaluated. Interestingly a selective antiproliferative activity was observed for cancerous cells with prominence to LNCaP within the most potent O- and/or N-benzylic and -hexyl acetanilides. |
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Keywords: | Atropisomerism Axial chirality Cytotoxic evaluation Dynamic VT-NMR Nimesulide analogues ortho-(Alkylchalcogen)acetanilides |
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