New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculations
Samo za registrovane korisnike
2014
Autori
Hmuda, SleemTrišović, Nemanja
Rogan, Jelena R.
Poleti, Dejan
Vitnik, Željko
Vitnik, Vesna
Valentić, Nataša V.
Bozic, Biljana
Ušćumlić, Gordana
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Hydantoin / Antiproliferative activity / X-ray structure determination / Quantum chemical calculations / Natural bond orbital analysisIzvor:
Monatshefte Fur Chemie, 2014, 145, 5, 821-833Izdavač:
- Springer Wien, Wien
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
- 0-3D nanostrukture za primenu u elektronici i obnovljivim izvorima energije: sinteza, karakterizacija i procesiranje (RS-MESTD-Integrated and Interdisciplinary Research (IIR or III)-45007)
- Racionalni dizajn i sinteza biološki aktivnih i koordinacionih jedinjenja i funkcionalnih materijala, relevantnih u (bio)nanotehnologiji (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
Institucija/grupa
IHTMTY - JOUR AU - Hmuda, Sleem AU - Trišović, Nemanja AU - Rogan, Jelena R. AU - Poleti, Dejan AU - Vitnik, Željko AU - Vitnik, Vesna AU - Valentić, Nataša V. AU - Bozic, Biljana AU - Ušćumlić, Gordana PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1518 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 VL - 145 IS - 5 SP - 821 EP - 833 DO - 10.1007/s00706-013-1149-6 ER -
@article{ author = "Hmuda, Sleem and Trišović, Nemanja and Rogan, Jelena R. and Poleti, Dejan and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša V. and Bozic, 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", volume = "145", number = "5", pages = "821-833", doi = "10.1007/s00706-013-1149-6" }
Hmuda, S., Trišović, N., Rogan, J. R., Poleti, D., Vitnik, Ž., Vitnik, V., Valentić, N. V., Bozic, 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 S, Trišović N, Rogan JR, Poleti D, Vitnik Ž, Vitnik V, Valentić NV, Bozic 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, Trišović, Nemanja, Rogan, Jelena R., Poleti, Dejan, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša V., Bozic, 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 . .