Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions
Само за регистроване кориснике
2020
Аутори
Lazić, Anita M.Đorđević, Ivana S.
Radovanović, Lidija D.
Popović, Dragan M.
Rogan, Jelena R.
Janjić, Goran V.
Trišović, Nemanja P.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater cont...ribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.
Кључне речи:
chiral recognition / drugs / fragment-based analysis / molecular docking / noncovalent interactionsИзвор:
Chempluschem, 2020, 85, 6, 1220-1232Издавач:
- Wiley-VCH Verlag
Финансирање / пројекти:
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200135 (Универзитет у Београду, Технолошко-металуршки факултет) (RS-MESTD-inst-2020-200135)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200287 (Иновациони центар Технолошко-металуршког факултета у Београду доо) (RS-MESTD-inst-2020-200287)
DOI: 10.1002/cplu.202000273
ISSN: 2192-6506
PubMed: 32515167
WoS: 000544057700017
Scopus: 2-s2.0-85086356663
Колекције
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Lazić, Anita M. AU - Đorđević, Ivana S. AU - Radovanović, Lidija D. AU - Popović, Dragan M. AU - Rogan, Jelena R. AU - Janjić, Goran V. AU - Trišović, Nemanja P. PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4504 AB - A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit. PB - Wiley-VCH Verlag T2 - Chempluschem T1 - Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions EP - 1232 IS - 6 SP - 1220 VL - 85 DO - 10.1002/cplu.202000273 ER -
@article{ author = "Lazić, Anita M. and Đorđević, Ivana S. and Radovanović, Lidija D. and Popović, Dragan M. and Rogan, Jelena R. and Janjić, Goran V. and Trišović, Nemanja P.", year = "2020", abstract = "A racemic spirohydantoin derivative with two aromatic substituents, a tetralin and a 4-methoxybenzyl unit, was synthesized and its crystal structure was determined. To define the relationship between molecular stereochemistry and spatial association modes, development of the crystal packing was analyzed through cooperativity of intermolecular interactions. Homo and heterochiral dimeric motifs were stabilized by intermolecular N-H...O, C-H...O, C-H...pi interactions and parallel interactions at large offsets (PILO), thus forming alternating double layers. The greatest contribution to the total stabilization came from a motif of opposite enantiomers linked by N-H...O bonds (interaction energy=-13.72 kcal/mol), followed by a homochiral motif where the 4-methoxybenzyl units allowed C-H...pi, C-H...O interactions and PILO (interaction energy=-11.56 kcal/mol). The number of the contact fragments in the environment of the tetralin unit was larger, but the 4-methoxybenzyl unit had greater contribution to the total stabilization. The statistical analysis of the data from the Cambridge Structural Database (CSD) showed that this is a general trend. The compound is a potential inhibitor of kinase enzymes and antigen protein-coupled receptors. A correlation between the docking study and the results of the CSD analysis can be drawn. Due to a greater flexibility, the 4-methoxybenzyl unit is more adaptable for interactions with the biological targets than the tetralin unit.", publisher = "Wiley-VCH Verlag", journal = "Chempluschem", title = "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions", pages = "1232-1220", number = "6", volume = "85", doi = "10.1002/cplu.202000273" }
Lazić, A. M., Đorđević, I. S., Radovanović, L. D., Popović, D. M., Rogan, J. R., Janjić, G. V.,& Trišović, N. P.. (2020). Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem Wiley-VCH Verlag., 85(6), 1220-1232. https://doi.org/10.1002/cplu.202000273
Lazić AM, Đorđević IS, Radovanović LD, Popović DM, Rogan JR, Janjić GV, Trišović NP. Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions. in Chempluschem. 2020;85(6):1220-1232. doi:10.1002/cplu.202000273 .
Lazić, Anita M., Đorđević, Ivana S., Radovanović, Lidija D., Popović, Dragan M., Rogan, Jelena R., Janjić, Goran V., Trišović, Nemanja P., "Self-Assembly and Biorecognition of a Spirohydantoin Derived from alpha-Tetralone: Interplay between Chirality and Intermolecular Interactions" in Chempluschem, 85, no. 6 (2020):1220-1232, https://doi.org/10.1002/cplu.202000273 . .