702-62-5Relevant articles and documents
On the supramolecular outcomes of fluorination of cyclohexane-5-spirohydantoin derivatives
Gak Simi?, Kristina,?or?evi?, Ivana,Lazi?, Anita,Radovanovi?, Lidija,Petkovi?-Benazzouz, Marija,Rogan, Jelena,Tri?ovi?, Nemanja,Janji?, Goran
, p. 2606 - 2622 (2021)
The quantitative assessment of intermolecular interactions and their cooperative effects has been performed in spirohydantoin-based model compounds, 3-benzoyl-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-fluorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), through single crystal X-ray crystallography and quantum chemical studies. In both crystal structures, molecules generate the same hydrogen-bonded centrosymmetric R22(8) synthon. The extended supramolecular architectures depend on the C-HO, C-Hπ, stacking interactions and parallel interactions at large offsets, which lead to molecular sheets and further, with the assistance of the C-HF interaction in the case of2, to three-dimensional networks. Electrostatic potential maps have indicated that formation of the intermolecular FF interaction in the crystal structure of2results in a new region with a larger surface area and a higher negative potential in comparison to the individual fluorine atoms. Establishment of this interaction leads to strengthening of the interaction of one of the fluorine atoms with a third molecule from the environment which does not interact with both of them. When this third molecule interacts with both fluorine atoms simultaneously, the calculations have shown that the effect of strengthening of the individual interactions due to formation of the FF interaction is absent.
Synthesis, characterization and antimicrobial activity of nalidixic acid derivatives with spirohydantoins
Marinov, Marin,Kostova, Iliana,Naydenova, Emilia,Prodanova, Rumyana,Stoyanov, Neyko
, p. 2787 - 2793 (2019/08/01)
This article presents the synthesis of a series of amides, based on the interaction of several 3-aminospirohydantoins with nalidixic acid. The target compounds were characterized by physicochemical parameters, IR, 1H and 13C NMR spectral data. The antimicrobial activity of the products obtained was determined against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, Gram-negative bacteria Escherichia coli, Pseudomonas aeruginosa and Salmonella abony, the yeasts Candida albicans and Saccharomyces cerevisiae and the molds Penicillium chrysogenum and Aspergillus niger. The relationship between structure and biological activity of the products obtained was discussed. It was found that the most effective compounds are tetralin (5f) and indane (5g) derivatives, which exhibit a pronounced antimicrobial activity against both tested Gram-positive and Gram-negative bacteria.
Towards understanding intermolecular interactions in hydantoin derivatives: the case of cycloalkane-5-spirohydantoins tethered with a halogenated benzyl moiety
Lazi?, Anita,Tri?ovi?, Nemanja,Radovanovi?, Lidija,Rogan, Jelena,Poleti, Dejan,Vitnik,Vitnik, Vesna,U??umli?, Gordana
, p. 469 - 483 (2017/01/29)
A series of cycloalkane-5-spirohydantoins bearing a halogeno substituted benzyl group (X = Cl and Br) in position 3 has been synthesized and their structures (1-6) have been determined by a single crystal X-ray diffraction method. These compounds have multiple functional groups, which allow greater competition and/or cooperation among the different intermolecular interactions in the formation of their crystal structures. The molecules are linked together by paired N-H?O hydrogen bonds in R22(8) rings, while the C-H?O interactions lead to their further association into double chains. The contribution of the cycloalkyl ring depends on its conformational flexibility and the multiple C-H donor implications. In the case of compounds 1-4 bearing the cyclopentyl or the cyclohexyl ring, halogen bonding (X?O) interactions give rise to a supramolecular pseudo-hexagonal network. In addition, the C-H?X interactions with a higher degree of multifurcation at the halogen acceptor have an important role in the formation of the crystal structure. Regarding compounds 5 and 6 with the cycloheptane ring, the X?O interaction is absent, and along with the C-H?X interactions, these compounds realize an alternative crystal structure with an emphasis on the X?π interactions. The lattice energies of all these crystal structures, as well as the intermolecular pair energies, have been calculated using PIXEL and further partitioned into coulombic, dispersive, polarization and repulsive factors. The crystal structures have also been subjected to Hirshfeld surface analysis which reveals that approximately 75% of the close contacts correspond to relatively weak interactions. The application of both concepts has provided a new insight into the relationship between the molecular interactions and crystal structures of the hydantoin derivatives.