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In silico design of new pyrimidine-2,4-dione derivatives as promising inhibitors for HIV Reverse Transcriptase-associated RNase H using 2D-QSAR modeling and (ADME/Tox) properties


 
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1. Title Title of document In silico design of new pyrimidine-2,4-dione derivatives as promising inhibitors for HIV Reverse Transcriptase-associated RNase H using 2D-QSAR modeling and (ADME/Tox) properties
 
2. Creator Author's name, affiliation, country Y. El Masaoudy; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco
 
2. Creator Author's name, affiliation, country K. Tabti; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco; Morocco
 
2. Creator Author's name, affiliation, country Y. Koubi; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco; Morocco
 
2. Creator Author's name, affiliation, country H. Maghat; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco; Morocco
 
2. Creator Author's name, affiliation, country T. Lakhlifi; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco; Morocco
 
2. Creator Author's name, affiliation, country M. Bouachrine; Molecular Chemistry and Natural Substances Laboratory (MCNSL), Department of Chemistry, Faculty of Sciences, University Moulay Ismail, Meknes, Morocco
 
3. Subject Discipline(s)
 
3. Subject Keyword(s) Pyrimidine-2,4-dione; HIV RT RNase; 2D-QSAR; Lipinski’s RO5; ADME/Tox properties
 
4. Description Abstract The main target of present QSAR modeling is to pave the way for the development of new pyrimidine-2,4-dione derivatives and predict their HIV reverse transcriptase-associated RNase H inhibitory activity. To accelerate this process, linear and non-linear models of thirty-nine pyrimidine-2,4-dione derivatives have been constructed by exploiting PCA, MLR, and MNLR statistical techniques available in the XLSTAT software, as well as the (DFT/ Beck3LYP/6-31G (d,p)) approach. Among the 16 quantum and physicochemical descriptors measured, only four optimal molecular descriptors have been employed to perform QSAR models, i.e., density, number of H-bond acceptors, octanol/water partition coefficient, and LUMO energy. The Loo/cross-validation procedure, the Y-scrambling test, Golbraikh-Tropsha’s criteria and the applicability area have all been utilized to evaluate the linear model's performance accuracy. Likewise, the nonlinear model's predictive power has been measured internally through the Loo/cross-validation procedure with coefficient R_(CV(LOO))^2  and externally through test set compounds with external prediction coefficient R_pred^2. Herein, both MLR and MNLR models which exhibited excellent performance and met OECD criteria were exploited to predict inhibitory activities. By analyzing the structural characteristics of the studied compounds encoded in the afore-mentioned descriptors along with their effects on pIC50 inhibitory activity, we have been able to design eleven new chemical inhibitors. All of these inhibitors with new substituents displayed significantly higher HIV RT-associated RNase H inhibitory activities than the existing ones, as well as satisfactory results in silico ADME/Toxicity assessments.
 
5. Publisher Organizing agency, location
 
6. Contributor Sponsor(s)
 
7. Date (YYYY-MM-DD) 21-02-2023
 
8. Type Status & genre Peer-reviewed Article
 
8. Type Type
 
9. Format File format PDF
 
10. Identifier Uniform Resource Identifier https://revues.imist.ma/index.php/morjchem/article/view/35455
 
10. Identifier Digital Object Identifier (DOI) https://doi.org/10.48317/IMIST.PRSM/morjchem-v11i2.35455
 
11. Source Title; vol., no. (year) Moroccan Journal of Chemistry; Vol 11, No 2 (2023)
 
12. Language English=en en
 
13. Relation Supp. Files
 
14. Coverage Geo-spatial location, chronological period, research sample (gender, age, etc.)
 
15. Rights Copyright and permissions Copyright (c) 2023 Moroccan Journal of Chemistry