Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/qsar-characterization-of-new-synthesized-hydantoins-with-rFdu1tl3Vm
References (43)
-
El Rabtti, M. Natić, D. Milojković-Opsenica, J. Trifković, I. Vučković, V. Vajs, ivoslav Tešic (2012)
RP TLC-based lipophilicity assessment of some natural and synthetic coumarinsJournal of the Brazilian Chemical Society, 23
-
Sleem Hmuda, N. Trišović, J. Rogan, D. Poleti, Ž. Vitnik, V. Vitnik, Nataša Valentić, Biljana Božić, G. Uscumlic (2014)
New derivatives of hydantoin as potential antiproliferative agents: biological and structural characterization in combination with quantum chemical calculationsMonatshefte für Chemie - Chemical Monthly, 145
-
W. Lambert (1993)
Modeling oil-water partitioning and membrane permeation using reversed-phase chromatographyJournal of Chromatography A, 656
-
E. Bate-smith, R. Westall (1950)
Chromatographic behaviour and chemical structure I. Some naturally occuring phenolic substancesBiochimica et Biophysica Acta, 4
-
D. Sergent, Qian Wang, N. Sasaki, J. Ouazzani (2008)
Synthesis of hydantoin analogues of (2S,3R,4S)-4-hydroxyisoleucine with insulinotropic properties.Bioorganic & medicinal chemistry letters, 18 15
-
A. Zissimos, M. Abraham, Matthew Barker, K. Box, K. Tam (2002)
Calculation of Abraham descriptors from solvent–water partition coefficients in four different systems; evaluation of different methods of calculationJournal of The Chemical Society-perkin Transactions 1
-
Á. Sándi, M. Nagy, L. Szepesy (1998)
Characterization of reversed-phase columns using the linear free energy relationship. III. Effect of the organic modifier and the mobile phase composition.Journal of Chromatography A, 893
-
L. Somsák, L. Kovács, M. Tóth, E. Ősz, L. Szilágyi, Z. Györgydeák, Z. Dinya,, T. Docsa, B. Tóth, P. Gergely (2001)
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.Journal of medicinal chemistry, 44 17
-
J. Trifunovic, V. Borčić, S. Vukmirović, Svetlana Kon, M. Mikov (2016)
Retention data of bile acids and their oxo derivatives in characterization of pharmacokinetic properties and in silico ADME modeling.European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 92
-
E. Naydenova, N. Pencheva, J. Popova, N. Stoyanov, M. Lazarova, B. Aleksiev (2002)
Aminoderivatives of cycloalkanespirohydantoins: synthesis and biological activity.Farmaco, 57 3
-
Ewelina Rutkowska, Karolina PAJ•K, Krzysztof J”èWIAK (2012)
LIPOPHILICITY ñ METHODS OF DETERMINATION AND ITS ROLE IN MEDICINAL CHEMISTRY -
Jie Dong, Ning-Ning Wang, Zhi-Jiang Yao, Lin Zhang, Yan Cheng, D. Ouyang, Aiping Lu, Dongsheng Cao (2018)
ADMETlab: a platform for systematic ADMET evaluation based on a comprehensively collected ADMET databaseJournal of Cheminformatics, 10
-
S. Scholl, A. Koch, D. Henning, G. Kempter, E. Kleinpeter (1999)
The Influence of Structure and Lipophilicity of Hydantoin Derivatives on Anticonvulsant ActivityStructural Chemistry, 10
-
J. Platts, Steven Oldfield, Maria Reif, Alessandra Palmucci, E. Gabano, D. Osella (2006)
The RP-HPLC measurement and QSPR analysis of logP(o/w) values of several Pt(II) complexes.Journal of inorganic biochemistry, 100 7
-
(1995)
Test No. 107: Partition Coefficient (n-octanol/water): Shake Flask Method -
I. Gomez-Monterrey, G. Santelli, P. Campiglia, D. Califano, Fabiano Falasconi, C. Pisano, L. Vesci, T. Lama, P. Grieco, E. Novellino (2005)
Synthesis and cytotoxic evaluation of novel spirohydantoin derivatives of the dihydrothieno[2,3-b]naphtho-4,9-dione system.Journal of medicinal chemistry, 48 4
-
M. Vitha, P. Carr (2006)
The chemical interpretation and practice of linear solvation energy relationships in chromatography.Journal of chromatography. A, 1126 1-2
-
J. Kossakowski, T. Zawadowski, J. Turło, J. Kleps (1998)
Synthesis of N-(4-aryl-1-piperazinylbutyl)-substituted 7,8-benzo-1,3-diazaspiro[4,5]decane-2,4-dione derivatives with potential anxiolytic activity.Farmaco, 53 2
-
K. Kimata, Kazufusa Iwaguchi, S. Onishi, K. Jinno, R. Eksteen, K. Hosoya, M. Araki, N. Tanaka (1989)
Chromatographic Characterization of Silica C18 Packing Materials. Correlation between a Preparation Method and Retention Behavior of Stationary PhaseJournal of Chromatographic Science, 27
-
J. Dorsey, M. Khaledi (1993)
Hydrophobicity estimations by reversed‐phase liquid chromatography, 656
-
A. Katritzky, M. Kuanar, S. Slavov, C. Hall, M. Karelson, Iiris Kahn, D. Dobchev (2010)
Quantitative correlation of physical and chemical properties with chemical structure: utility for prediction.Chemical reviews, 110 10
-
J. Obniska, H. Byrtus, K. Kamiński, M. Pawłowski, M. Szczesio, J. Karolak‐Wojciechowska (2010)
Design, synthesis, and anticonvulsant activity of new N-Mannich bases derived from spirosuccinimides and spirohydantoins.Bioorganic & medicinal chemistry, 18 16
-
Milica Karadžić, L. Jevric, A. Mandic, S. Markov, S. Podunavac-Kuzmanovic, Strahinja Kovačević, Andrea Nikolić, Aleksandar Oklješa, M. Sakač, K. Penov-Gaši (2017)
Chemometrics approach based on chromatographic behavior, in silico characterization and molecular docking study of steroid analogs with biomedical importanceEuropean Journal of Pharmaceutical Sciences, 105
-
Meng Lv, Zhuo Chen, Gaoyun Hu, Qianbin Li (2015)
Therapeutic strategies of diabetic nephropathy: recent progress and future perspectives.Drug discovery today, 20 3
-
Abubaker Atrrog, M. Natić, Tomislav Tosti, D. Milojković-Opsenica, I. Dordević, V. Tešević, M. Jadranin, S. Milosavljevic, M. Lazić, S. Radulović, Ž. Tešić (2009)
Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro.Biomedical chromatography : BMC, 23 3
-
E. Soczewiński, G. Matysik (1968)
Two types of RM-composition relationships in liquid-liquid partition chromatographyJournal of Chromatography A, 32
-
E. C. Bate‐Smith, R. G. Westall (1950)
Chromatographic behaviour and chemical structure, 4
-
Hardik Patel, J. Sarra, F. Caruso, M. Rossi, U. Doshi, R. Stephani (2006)
Synthesis and anticonvulsant activity of new N-1',N-3'-disubstituted-2'H,3H,5'H-spiro-(2-benzofuran-1,4'-imidazolidine)-2',3,5'-triones.Bioorganic & medicinal chemistry letters, 16 17
-
John Dorsey, M. Khaledi (1993)
Hydrophobicity estimations by reversed-phase liquid chromatography. Implications for biological partitioning processes.Journal of chromatography, 656 1-2
-
T. Mosmann (1983)
Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays.Journal of immunological methods, 65 1-2
-
C. Kavitha, Mridula Nambiar, C. Kumar, B. Choudhary, K. Muniyappa, K. Rangappa, S. Raghavan (2009)
Novel derivatives of spirohydantoin induce growth inhibition followed by apoptosis in leukemia cells.Biochemical pharmacology, 77 3
-
M. Abraham, Adam Ibrahim, A. Zissimos (2004)
Determination of sets of solute descriptors from chromatographic measurements.Journal of chromatography. A, 1037 1-2
-
A. Czopek, M. Kołaczkowski, Adam Bucki, H. Byrtus, M. Pawłowski, G. Kazek, A. Bojarski, Agata Piaskowska, J. Kalinowska‐Tłuścik, A. Partyka, A. Wesołowska (2015)
Novel spirohydantoin derivative as a potent multireceptor-active antipsychotic and antidepressant agent.Bioorganic & medicinal chemistry, 23 13
-
M. Abraham (1993)
Application of solvation equations to chemical and biochemical processesPure and Applied Chemistry, 65
-
M. Yamagishi, Y. Yamada, K. Ozaki, M. Asao, R. Shimizu, M. Suzuki, M. Matsumoto, Y. Matsuoka, K. Matsumoto (1992)
Biological activities and quantitative structure-activity relationships of spiro[imidazolidine-4,4'(1'H)-quinazoline]-2,2',5(3'H)-triones as aldose reductase inhibitors.Journal of medicinal chemistry, 35 11
-
Alshimaa Aboeldahab, E. Beshr, Mai Shoman, Safwat Rabea, O. Aly (2018)
Spirohydantoins and 1,2,4-triazole-3-carboxamide derivatives as inhibitors of histone deacetylase: Design, synthesis, and biological evaluation.European journal of medicinal chemistry, 146
-
Qifeng Zhu, Yuanhu Pan, Zaixu Xu, Ruimin Li, G. Qiu, Wenjin Xu, Xianbing Ke, Lamei Wu, Xianming Hu (2009)
Synthesis and potential anticonvulsant activity of new N-3-substituted 5,5-cyclopropanespirohydantoins.European journal of medicinal chemistry, 44 1
-
N. Milošević, S. Stojanovic, K. Penov-Gaši, N. Perišić-Janjić, R. Kaliszan (2014)
Reversed- and normal-phase liquid chromatography in quantitative structure retention-property relationships of newly synthesized seco-androstene derivatives.Journal of pharmaceutical and biomedical analysis, 88
-
V. Pliska, B. Testa, H. Waterbeemd (1996)
Lipophilicity in Drug Action and Toxicology: Pliška/Lipophilicity -
Hisashi Suzuki, M. Kneller, D. Rock, Jeffrey Jones, W. Trager, A. Rettie (2004)
Active-site characteristics of CYP2C19 and CYP2C9 probed with hydantoin and barbiturate inhibitors.Archives of biochemistry and biophysics, 429 1
-
M. Bialer (2012)
Chemical properties of antiepileptic drugs (AEDs).Advanced drug delivery reviews, 64 10
-
F. Settimo, G. Primofiore, C. Motta, S. Salerno, E. Novellino, G. Greco, A. Lavecchia, S. Laneri, E. Boldrini (2005)
Spirohydantoin derivatives of thiopyrano[2,3-b]pyridin-4(4H)-one as potent in vitro and in vivo aldose reductase inhibitors.Bioorganic & medicinal chemistry, 13 2
-
Mitsuharu Ohno, Tsutomu Abe (1991)
Rapid colorimetric assay for the quantification of leukemia inhibitory factor (LIF) and interleukin-6 (IL-6).Journal of immunological methods, 145 1-2
- Publisher
- Wiley
- Copyright
- © 2019 John Wiley & Sons, Ltd.
- ISSN
- 0269-3879
- eISSN
- 1099-0801
- DOI
- 10.1002/bmc.4539
- Publisher site
- See Article on Publisher Site
Abstract
Hydantois have been identified as constituents of a number of pharmacologically active molecules. In the present study, we have examined in vitro antiproliferative activity against human colon cancer cell lines HCT‐116 of three series of 3‐(4‐substituted benzyl)‐hydantoins with various substituent attached in position 5 of the hydantoin ring. Since the investigated compounds have recently been synthesized and show antiproliferative activity, a good understanding of the properties of the potential drug responsible for their pharmacokinetics is an important goal for their further development. One of the important properties is lipophilicity. Lipophilicity has been assessed by reversed‐phase liquid chromatography (high‐performance thin‐layer chromatography and high‐pressure liquid chromatography) by means of direct and indirect (using calibration curve) methods. Chromatographic lipophilicity indices in addition to calculated logP values were compared by hierarchical cluster analysis. The linear solvation energy relationship approach was used to understand and compare the types and relative strength of the molecular interactions that occur in the chromatographic as well as in the n‐octanol–water partitioning systems. Finally, correlation between in silico pharmacokinetic predictors and antiproliferative activity was examined. Preliminary quantitative structure–activity relationship modeling indicates that pharmacokinetic predictors capture only one‐quarter of all chemical features that are important for antiproliferative activity itself. Among selected descriptors are chromatographic lipophilicity indices.
Journal
Biomedical Chromatography – Wiley
Published: Aug 1, 2019
Keywords: ; ; ; ;