A novel type of organometallic 2-R-2,4-dihydro- 1H-3,1-benzoxazine with R = [M(η5-C5H4)(CO)3] (M = Re or Mn) units. Experimental and computational studies of the effect of substituent R on ring-chain tautomerism
| Autor: | Ramon Messeguer, A. Hugo Klahn, Vania Artigas, Mercè Font-Bardia, Juan Oyarzo, Ramón Bosque, Rodrigo Arancibia, Carme Calvis, Carlos P. Silva, Patricia M. Toro, Concepción López |
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| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
Crystallography Double bond 010405 organic chemistry Stereochemistry Antiparasitic medicine.drug_class Cristal·lografia Substituent Crystal structure 010402 general chemistry Ring (chemistry) Electrochemistry 01 natural sciences Tautomer 0104 chemical sciences Inorganic Chemistry chemistry.chemical_compound chemistry Chain (algebraic topology) medicine Estructura cristal·lina (Sòlids) Layer structure (Solids) |
| Zdroj: | Dipòsit Digital de la UB Universidad de Barcelona |
| Popis: | The syntheses, characterization, X-ray crystal structures, electrochemical properties and anticancer and 35 antichagasic activities of the first examples of 2-substituted 2,4-dihydro-1H-3,1-benzoxazines with 36 halfsandwich organometallic arrays, [M(η5-C5H4)(CO)3] (M = Re or Mn), at position-2 are described. 37 Experimental and computational studies based on DFT calculations on the open forms [Schiff bases of 38 general formulae R-CHvN-C6H4-2-CH2OH] (5), with R = ferrocenyl (a), phenyl (b), cyrhetrenyl (c) or 39 cymantrenyl (d), and their tautomeric forms (2-substituted 2,4-dihydro-1H-3,1 benzoxazines) 40 haveallowed us to establish the influence of substituents a-d and solvents on: (a) the extent of 41 tautomeric equilibria (5a-5d) ↔ (6a-6d) and (b) their electrochemical properties and the electronic 42 distribution on the open and closed forms. Despite the formal similarity between 6c and 6d, their 43 anticancer and antiparasitic activities are markedly different. Compound 6d is inactive in the HCT116, 44 MDA-MB231 and MCF7 cancer cell lines, but 6c shows moderate activity in the latter cell line, while 45 the Mn(I) complex (6d) is a more potent anti-Trypanosoma cruzi agent than its Re(I) analogue (6c). |
| Databáze: | OpenAIRE |
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