New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
Само за регистроване кориснике
2014
Аутори
Hmuda, Sleem F.Trišović, Nemanja
Rogan, Jelena
Poleti, Dejan
Vitnik, Željko
Vitnik, Vesna
Valentić, Nataša
Božić, Biljana
Ušćumlić, Gordana
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. Th...e data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.
Кључне речи:
Hydantoin / Antiproliferative activity / X-ray structure determination / Quantum chemical calculations / Natural bond orbital analysisИзвор:
Monatshefte Fur Chemie, 2014, 145, 5, 821-833Издавач:
- Springer Wien, Wien
Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
- 0-3D наноструктуре за примену у електроници и обновљивим изворима енергије: синтеза, карактеризација и процесирање (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-45007)
- Рационални дизајн и синтеза биолошки активних и координационих једињења и функционалних материјала, релевантних у (био)нанотехнологији (RS-MESTD-Basic Research (BR or ON)-172035)
DOI: 10.1007/s00706-013-1149-6
ISSN: 0026-9247
WoS: 000334511300014
Scopus: 2-s2.0-84899649174
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Hmuda, Sleem F. AU - Trišović, Nemanja AU - Rogan, Jelena AU - Poleti, Dejan AU - Vitnik, Željko AU - Vitnik, Vesna AU - Valentić, Nataša AU - Božić, Biljana AU - Ušćumlić, Gordana PY - 2014 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2862 AB - Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity. PB - Springer Wien, Wien T2 - Monatshefte Fur Chemie T1 - New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations EP - 833 IS - 5 SP - 821 VL - 145 DO - 10.1007/s00706-013-1149-6 ER -
@article{ author = "Hmuda, Sleem F. and Trišović, Nemanja and Rogan, Jelena and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša and Božić, Biljana and Ušćumlić, Gordana", year = "2014", abstract = "Two new series of hydantoin derivatives, 3-(4-substituted benzyl)-5,5-diphenyl- and 3-(4-substituted benzyl)-5-ethyl-5-phenylhydantoins, were synthesized and their antiproliferative activity was tested against human colon cancer HCT-116 and breast cancer MDA-MB-231 cell lines. The presence of different substituents on both hydantoin and benzyl moieties changed the antiproliferative activity of the investigated hydantoins, whereby most of the compounds showed superior antiproliferative activity against MDA-MB-231 than against the HCT-116 cell line. The structure of three compounds was studied by single-crystal X-ray diffraction. The general structural characteristic is the presence of N-H center dot center dot center dot O hydrogen bonds in crystal packings. The molecular geometry and bonding features of the investigated hydantoins in the ground states were calculated using the density functional method. The relationship between structure and antiproliferative activity was discussed. The data presented in this investigation afford guidelines for the preparation of new hydantoin derivatives with greater antiproliferative activity.", publisher = "Springer Wien, Wien", journal = "Monatshefte Fur Chemie", title = "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations", pages = "833-821", number = "5", volume = "145", doi = "10.1007/s00706-013-1149-6" }
Hmuda, S. F., Trišović, N., Rogan, J., Poleti, D., Vitnik, Ž., Vitnik, V., Valentić, N., Božić, B.,& Ušćumlić, G.. (2014). New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie Springer Wien, Wien., 145(5), 821-833. https://doi.org/10.1007/s00706-013-1149-6
Hmuda SF, Trišović N, Rogan J, Poleti D, Vitnik Ž, Vitnik V, Valentić N, Božić B, Ušćumlić G. New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations. in Monatshefte Fur Chemie. 2014;145(5):821-833. doi:10.1007/s00706-013-1149-6 .
Hmuda, Sleem F., Trišović, Nemanja, Rogan, Jelena, Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša, Božić, Biljana, Ušćumlić, Gordana, "New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations" in Monatshefte Fur Chemie, 145, no. 5 (2014):821-833, https://doi.org/10.1007/s00706-013-1149-6 . .