Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives
Apstrakt
Modeling properties of newly synthesized compounds is important for both understanding their activity and predicting their interactions. This paper describes the evaluation of the lipophilicity of the newly synthesized cycloalkylspiro-5-hydantoins by experimental and calculation methods. The chromatographic lipophilicity (R-M(0)) of the analyzed compounds was determined by reversed-phase liquid chromatographic system consisting of RP-18 stationary phase and methanol-water mobile phase. Correlation coefficients between R-M(0) values and the predicted log P were above 0.93, indicating a strong linear relationship between the variables. Multivariate data analysis applied in this study enabled the comparison of the lipophilicity and the structure of the investigated compounds using solely information obtained from thin-layer chromatography. Hierarchical clustering analysis (HCA) reveals a high similarity between R-M(0) and miLogP whereas squared log Ps such as ALOGP2 and MLOGP2 were distin...ct from R-M(0). HCA classifies the investigated compounds into three clusters according to lipophilicity. Principal component analysis (PCA) yields two principal components which explained gt 99.19% total variance. The changes in the lipophilicity of the substituents attached in the molecule are reflected in the value of PCs. An increase in the lipophilicity of spiro substituent results in a decrease of values of both PC1 and PC2. The increase in the lipophilicity of R substituent decreases the value of PC1 and increases the value of PC2. The positive value of PC1 is typical for the compounds with the electron withdrawing groups such as CN, NO2, or OCH3.
Ključne reči:
Quantitative structure-retention relationships / Cycloalkanespiro-5-hydantoins / Lipophilicity / Hierarchical clustering analysis / Principal component analysisIzvor:
JPC-Journal of Planar Chromatography-Modern Tlc, 2016, 29, 4, 281-286Izdavač:
- Akademiai Kiado Zrt, Budapest
Finansiranje / projekti:
- Proučavanje sinteze, strukture i aktivnosti organskih jedinjenja prirodnog i sintetskog porekla (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.1556/1006.2016.29.4.6
ISSN: 0933-4173
WoS: 000385039300007
Scopus: 2-s2.0-84979697043
Institucija/grupa
Inovacioni centarTY - JOUR AU - Đaković-Sekulić, Tatjana AU - Vastag, Gyongyi AU - Tot, Kristina AU - Tot, Jadranka AU - Lazić, Anita PY - 2016 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/3364 AB - Modeling properties of newly synthesized compounds is important for both understanding their activity and predicting their interactions. This paper describes the evaluation of the lipophilicity of the newly synthesized cycloalkylspiro-5-hydantoins by experimental and calculation methods. The chromatographic lipophilicity (R-M(0)) of the analyzed compounds was determined by reversed-phase liquid chromatographic system consisting of RP-18 stationary phase and methanol-water mobile phase. Correlation coefficients between R-M(0) values and the predicted log P were above 0.93, indicating a strong linear relationship between the variables. Multivariate data analysis applied in this study enabled the comparison of the lipophilicity and the structure of the investigated compounds using solely information obtained from thin-layer chromatography. Hierarchical clustering analysis (HCA) reveals a high similarity between R-M(0) and miLogP whereas squared log Ps such as ALOGP2 and MLOGP2 were distinct from R-M(0). HCA classifies the investigated compounds into three clusters according to lipophilicity. Principal component analysis (PCA) yields two principal components which explained gt 99.19% total variance. The changes in the lipophilicity of the substituents attached in the molecule are reflected in the value of PCs. An increase in the lipophilicity of spiro substituent results in a decrease of values of both PC1 and PC2. The increase in the lipophilicity of R substituent decreases the value of PC1 and increases the value of PC2. The positive value of PC1 is typical for the compounds with the electron withdrawing groups such as CN, NO2, or OCH3. PB - Akademiai Kiado Zrt, Budapest T2 - JPC-Journal of Planar Chromatography-Modern Tlc T1 - Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives EP - 286 IS - 4 SP - 281 VL - 29 DO - 10.1556/1006.2016.29.4.6 ER -
@article{ author = "Đaković-Sekulić, Tatjana and Vastag, Gyongyi and Tot, Kristina and Tot, Jadranka and Lazić, Anita", year = "2016", abstract = "Modeling properties of newly synthesized compounds is important for both understanding their activity and predicting their interactions. This paper describes the evaluation of the lipophilicity of the newly synthesized cycloalkylspiro-5-hydantoins by experimental and calculation methods. The chromatographic lipophilicity (R-M(0)) of the analyzed compounds was determined by reversed-phase liquid chromatographic system consisting of RP-18 stationary phase and methanol-water mobile phase. Correlation coefficients between R-M(0) values and the predicted log P were above 0.93, indicating a strong linear relationship between the variables. Multivariate data analysis applied in this study enabled the comparison of the lipophilicity and the structure of the investigated compounds using solely information obtained from thin-layer chromatography. Hierarchical clustering analysis (HCA) reveals a high similarity between R-M(0) and miLogP whereas squared log Ps such as ALOGP2 and MLOGP2 were distinct from R-M(0). HCA classifies the investigated compounds into three clusters according to lipophilicity. Principal component analysis (PCA) yields two principal components which explained gt 99.19% total variance. The changes in the lipophilicity of the substituents attached in the molecule are reflected in the value of PCs. An increase in the lipophilicity of spiro substituent results in a decrease of values of both PC1 and PC2. The increase in the lipophilicity of R substituent decreases the value of PC1 and increases the value of PC2. The positive value of PC1 is typical for the compounds with the electron withdrawing groups such as CN, NO2, or OCH3.", publisher = "Akademiai Kiado Zrt, Budapest", journal = "JPC-Journal of Planar Chromatography-Modern Tlc", title = "Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives", pages = "286-281", number = "4", volume = "29", doi = "10.1556/1006.2016.29.4.6" }
Đaković-Sekulić, T., Vastag, G., Tot, K., Tot, J.,& Lazić, A.. (2016). Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives. in JPC-Journal of Planar Chromatography-Modern Tlc Akademiai Kiado Zrt, Budapest., 29(4), 281-286. https://doi.org/10.1556/1006.2016.29.4.6
Đaković-Sekulić T, Vastag G, Tot K, Tot J, Lazić A. Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives. in JPC-Journal of Planar Chromatography-Modern Tlc. 2016;29(4):281-286. doi:10.1556/1006.2016.29.4.6 .
Đaković-Sekulić, Tatjana, Vastag, Gyongyi, Tot, Kristina, Tot, Jadranka, Lazić, Anita, "Quantitative Structure-Retention Relationships Modeling and Multivariate Data Analysis of Lipophilicity Data of New Spirohydantoin Derivatives" in JPC-Journal of Planar Chromatography-Modern Tlc, 29, no. 4 (2016):281-286, https://doi.org/10.1556/1006.2016.29.4.6 . .