New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
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2014
Authors
Hmuda, Sleem F.Trišović, Nemanja

Rogan, Jelena

Poleti, Dejan

Vitnik, Željko

Vitnik, Vesna

Valentić, Nataša

Božić, Biljana

Ušćumlić, Gordana

Article (Published version)

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Show full item recordAbstract
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.
Keywords:
Hydantoin / Antiproliferative activity / X-ray structure determination / Quantum chemical calculations / Natural bond orbital analysisSource:
Monatshefte Fur Chemie, 2014, 145, 5, 821-833Publisher:
- Springer Wien, Wien
Funding / projects:
- Study of the Synthesis, Structure and Activity of Natural and Synthetic Organic Compounds (RS-172013)
- Zero- to Three-Dimensional Nanostructures for Application in Electronics and Renewable Energy Sources: Synthesis, Characterization and Processing (RS-45007)
- Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology (RS-172035)
DOI: 10.1007/s00706-013-1149-6
ISSN: 0026-9247
WoS: 000334511300014
Scopus: 2-s2.0-84899649174
Institution/Community
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 . .