RESUMO
Thienylallylamines, readily accessible from the corresponding thienyl aldehydes, react with maleic and trifluoromethylmaleic anhydrides leading to the formation of acids with a thieno[2,3-f]isoindole core. The reaction sequence involves two successive steps: acylation of the nitrogen atom of the initial allylamine and the intramolecular Diels-Alder vinylarene (IMDAV) reaction. The scope and limitations of the proposed method were thoroughly investigated. It has been revealed with the aid of X-ray analysis and DFT calculations that the key step, the IMDAV reaction, proceeds through an exo-transition state, giving rise to the exclusive formation of a single diastereomer of the target heterocycle. The obtained functionally substituted thieno[2,3-f]isoindole carboxylic acids are potentially useful substrates for further transformations and bioscreening. The antimicrobial evaluation of the obtained compounds revealed that 1-oxo-2-(3-(trifluoromethyl)phenyl)hexahydrobenzo[4,5]thieno[2,3-f]isoindole-10-carboxylic acid is the most active sample in the synthesized library. It exhibits antibacterial activity against sensitive strains of Gram-positive bacteria, including S. aureus, Enterococcus faecium, Bacillus cereus, and Micrococcus luteus, as well as the Gram-negative bacteria E. coli and Pseudomonas fluorescens, with MIC values ranging from 4 to 64 µg mL-1. 9-Oxo-8-phenyloctahydronaphtho[2,1-d]thieno[2,3-f]isoindole-10-carboxylic acid showed antifungal activity against yeast culture C. albicans with a MIC value of 32 µM.
Assuntos
Escherichia coli , Staphylococcus aureus , Testes de Sensibilidade Microbiana , Antibacterianos/química , Ácidos Carboxílicos , IsoindóisRESUMO
In the title compound, C20H18N2S, the asymmetric unit comprises two similar mol-ecules (A and B). In mol-ecule A, the central thio-phene ring makes dihedral angles of 89.96â (12) and 57.39â (13)° with the 1H-pyrrole rings, which are bent at 83.22â (14)° relative to each other, and makes an angle of 85.98â (11)° with the phenyl ring. In mol-ecule B, the corresponding dihedral angles are 89.49â (13), 54.64â (12)°, 83.62â (14)° and 85.67â (11)°, respectively. In the crystal, mol-ecular pairs are bonded to each other by N-Hâ¯N inter-actions. N-Hâ¯π and C-Hâ¯π inter-actions further connect the mol-ecules, forming a three-dimensional network. A Hirshfeld surface analysis indicates that Hâ¯H (57.1% for mol-ecule A; 57.3% for mol-ecule B), Câ¯H/Hâ¯C (30.7% for mol-ecules A and B) and Sâ¯H/Hâ¯S (6.2% for mol-ecule A; 6.4% for mol-ecule B) inter-actions are the most important contributors to the crystal packing.
RESUMO
In the title compound, C24H21NO3S, the cyclopentene ring adopts an envelope conformation. In the crystal, mol-ecules are linked by C-Hâ¯π inter-actions, forming ribbons along the a axis. Inter-molecular C-Hâ¯O hydrogen bonds connect these ribbons to each other, forming layers parallel to the (01) plane. The mol-ecular packing is strengthened by van der Waals inter-actions between the layers. The inter-molecular contacts were qu-anti-fied using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing the relative contributions of the contacts to the crystal packing to be Hâ¯H 46.0%, Câ¯H/Hâ¯C 21.1%, Oâ¯H/Hâ¯O 20.6% and Sâ¯H/Hâ¯S 9.0%.
RESUMO
In the title compound, C15H15Br2NO2, two bridged tetra-hydro-furan rings adopt envelope conformations with the O atom as the flap. The pyrrolidine ring also adopts an envelope conformation with the spiro C atom as the flap. In the crystal, the mol-ecules are linked into dimers by pairs of C-Hâ¯O hydrogen bonds, thus generating R 2 2(18) rings. The crystal packing is dominated by Hâ¯H, Brâ¯H, Hâ¯π and Brâ¯π inter-actions. One of the Br atoms is disordered over two sites with occupation ratio of 0.833â (8):0.167â (8).