ABSTRACT
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%.
ABSTRACT
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.
Subject(s)
Escherichia coli , Staphylococcus aureus , Microbial Sensitivity Tests , Anti-Bacterial Agents/chemistry , Carboxylic Acids , IsoindolesABSTRACT
In the title compound, C25H17N3O5S2, intra-molecular π-π inter-actions [centroid-to-centroid distance = 3.5640â (9)â Å] are observed between the furan and benzene rings of the 4-cyano-phenyl group. In the crystal, mol-ecules are connected via C-Hâ¯O and C-Hâ¯N hydrogen bonds, forming layers parallel to the (100) plane. These layers are inter-connected by C-Hâ¯π inter-actions and weak van der Waals inter-actions. Hirshfeld surface analysis indicates that Hâ¯H (30.2%), Nâ¯H/Hâ¯N (22.3%), Câ¯H/Hâ¯C (17.9%) and Oâ¯H/Hâ¯O (15.4%) inter-actions make the most significant contributions to the crystal packing.
ABSTRACT
In the title compound, C22H19NO5S·C2D6OS, the central six-membered ring has a slightly distorted boat conformation, while the fused pyrrolidine ring adopts an envelope conformation. These conformations are stabilized by O-Hâ¯O hydrogen bonds between the main compound and solvent mol-ecules. In addition, intra-molecular C-Hâ¯O hydrogen bonds in the main mol-ecule form two S(6) rings. Mol-ecules are connected by pairs of inter-molecular C-Hâ¯O hydrogen bonds, forming dimers with a R 2 2(8) motif. These dimers form a three-dimensional network through O-Hâ¯O, O-Hâ¯S and C-Hâ¯O hydrogen bonds with each other directly and through solvent mol-ecules. In addition, weak π-π stacking inter-actions [centroid-to-centroid distances = 3.9937â (10) and 3.9936â (10)â Å, slippages of 2.034 and 1.681â Å] are observed. 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 41.7%, Oâ¯H/Hâ¯O 27.7%, Câ¯H/Hâ¯C 17.0%, and Sâ¯H/Hâ¯S 7.5%.
