Neural networks: Accurate nonlinear QSAR model for HEPT derivatives

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 4, 2003, Pages 1200-1207

  Douali, Latifa ^a   Villemin, Didier ^b   Cherqaoui, Driss ^a  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b 6 Bd du Maréchal Juin   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATIONAL METHODS; HYDROPHOBICITY; MULTILAYER NEURAL NETWORKS; ORGANIC COMPOUNDS; VIRUSES;

MOLECULAR DESCRIPTORS;

CHEMICAL ENGINEERING;

1 ((2 HYDROXYETHOXY)METHYL) 6 (PHENYLTHIO)THYMINE; 1-((2-HYDROXYETHOXY)METHYL)-6-(PHENYLTHIO)THYMINE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DRUG DERIVATIVE; RNA DIRECTED DNA POLYMERASE; RNA DIRECTED DNA POLYMERASE INHIBITOR; THYMINE;

ARTICLE; ARTIFICIAL NEURAL NETWORK; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; FACTUAL DATABASE; HUMAN; MULTIVARIATE ANALYSIS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SENSITIVITY AND SPECIFICITY;

ANTI-HIV AGENTS; DATABASES, FACTUAL; HIV-1 REVERSE TRANSCRIPTASE; HUMANS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; MULTIVARIATE ANALYSIS; NEURAL NETWORKS (COMPUTER); QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; REVERSE TRANSCRIPTASE INHIBITORS; SENSITIVITY AND SPECIFICITY; THYMINE;

EID: 0042199118     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci034047q     Document Type: Article

References (30)

1. Turner, B. G.; Summers, M. F. Structural Biology of HIV. J. Mol. Biol. 1999, 285, 1-32.
2. Shinazi, R. F. Competitive Inhibitors of Human Immunodeficiency Virus Reverse Transcriptase. Perspect. Drug Discovery Des. 1993, 1, 151-180.
3. De Clercq, E. Perspective of Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) in the Therapy of HIV-1 Infection. Il Farmaco 1999, 54, 26-45.
4. Esnouf, R.; Ren, J.; Ross, C.; Jones, Y.; Stammers, D.; Stuart, D. Mechanism of Inhibition of HIV-1 Reverse Transcriptase by Non-Nucleoside Inhibitors. Struct. Biol. 1995, 2, 303-308.
5. Miyasaka, T.; Tanaka, H.; Baba, M.; Hayakawa, H.; Walker, R. T.; Balzarini, J.; DeClercq, E. A Novel Lead for Specific anti-HIV-1 Agents: 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine. J. Med. Chem. 1989, 32, 2507-2509.
6. Tanaka, H.; Baba, M.; Hayakawa, H.; Sakamaki, T.; Miyasaka, T.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, S.; Walker, R. T.; Balzarini, J.; DeClercq, E. A New Class of HIV-1 Specific 6-Substituted Acyclouridine Derivatives: Synthesis and Anti-HIV Activity of 5- or 6- Substituted Analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 349-357.
7. Tanaka, H.; Baba, M.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, S.; Walker, R. T.; Miyasaka, T. Synthesis and Anti-HIV Activity of 2-,3-, and 4-Substituted Analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT). J. Med. Chem. 1991, 34, 1394-1399.
8. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; DeClercq, E.; Miyasaka, T. Structure-Activity Relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine Analogues: Effect of Substitutions at the C-6 Phenyl Ring and the C-5 Position on Anti-HIV-1 Activity. J. Med. Chem. 1992, 35, 337-345.
9. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; DeClercq, E.; Miyasaka, T. Synthesis and Antiviral Activity of Deoxy Analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) as Potent and Selective Anti-HIV Agents. J. Med. Chem. 1992, 35, 4713-4719.
10. Hansh, C.; Leo, A. Exploring QSAR. Fundamentals and Applications in Chemistry and Biology. American Chemical Society: Washington, DC, 1995.
11. Aoyama, T.; Suzuki, Y.; Ichikawa, H. Neural Networks Applied to Quantitative Structure-Activity Relationship Analysis. J. Med. Chem. 1990, 33, 2583-2590.
12. Zhu, J.; Chen, D.; Wu, P. Exploration of Artificial Neural System for Simulation of the Halogen-Exchange Fluorination Reaction. Comput. Chem. 1999, 23, 97-100.
13. Yan, A.; Jiao, G.; Hu, Z.; Fan, B. T. Use of Artificial Neural Networks to Predict the Gas Chromatographic Retention Index Data of Alkylbenzenes on Carbowax-20M. Comput. Chem. 2000, 24, 171-179.
14. Douali, L.; Villemin, D.; Cherqaoui, D. Comparative QSAR based on Neural Networks for the Anti-HIV Activity of HEPT Derivatives. Curr. Pharm. Des., in press.
15. Zupan, J.; Novic, M. General Type of a Uniform and Reversible Representation of Chemical Structures. Anal. Chim. Acta 1997, 348, 409-418.
16. Luco, J. M.; Ferretti, F. H. QSAR Based on Multiple Linear Regression and PLS Methods for the Anti-HIV Activity of a Large Group of HEPT Derivatives. J. Chem. Inf. Comput. Sci. 1997, 37, 392-401.
17. Garg, R.; Gupta, S. P.; Gao, H.; Babu, M. S. Debnath, A. K. Comparative Quantitative Structure-Activity Relationship Studies on Anti-HIV Drugs. Chem. Rev. 1999, 99, 3525-3601.
18. Jalali-Heravi, M.; Parastar, F. Use of Artificial Neural Networks in a QSAR Study of Anti-HIV Activity for a large Group of HEPT Derivatives. J. Chem. Inf. Comput. Sci. 2000, 40, 147-154.
19. Kireev, D. B.; Chretien, J. R.; Griersson, D. S.; Monneret, C. A. 3D QSAR Study of a Series of HEPT Analogues: The Influence of Conformational Mobility on HIV-1 Reverse Transcriptase Inhibition. J. Med. Chem. 1997, 40, 4257-4264.
20. Hannongbua, S.; Nivesnanond, K.; Lawtrakul, L.; Pungpo, P.; Wolschann, P. 3D-Quantitative Structure-Activity Relationships of HEPT Derivatives as HIV-1 Reverse Transcriptase Inhibitors, Based on Ab Initio Calculations. J. Chem. Inf. Comput. Sci. 2001, 41, 848-855.
21. Bazoui, H.; Zahouily, M.; Boulajaaj, S.; Sebti, S.; Zakarya, D. QSAR for anti-HIV activity of HEPT derivatives. SAR QSAR Environ. Res. 2002, 13, 567-577.
22. Gaudio, A. C.; Montanari, C. A. HEPT Derivatives as Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase: QSAR Studies agree with the Crystal Structures. J. Comput.-Aided Mol. Des. 2002, 16, 287-295.
23. Zupan, J.; Gasteiger, J. Neural Networks for Chemists. VCH-Wiley: Weinheim, Germany, 1993; p 207.
24. Andrea, T. A.; Kalayeh, H. Application of Neural Networks in Quantitative Structure-Activity Relationships of Dihydrofolate Reductase Inhibitors. J. Med. Chem. 1991, 34, 2824-2836.
25. So, S.; Richards, G. Application of Neural Networks: Quantitative Structure-Activity Relationships of the Derivatives of 2,4-Diamino-5- (substituted-benzyl) pyrimidines as DHFR Inhibitors. J. Med. Chem. 1992, 35, 3201-3207.
26. Freeman, J. A.; Skapura, D. M. Neural Networks Algorithms, Applications and Programming Techniques, Addison Wesley Publishing Company: Reading, MA, 1991.
27. Gasteiger, J.; Zupan, J. Neural Networks in Chemistry. Angew. Chem., Int. Ed. Engl. 1993, 32, 503-527.
28. Bishop, C. M. Neural Networks and their Applications. Rev. Sci. Instrum. 1994, 65, 1803-1832.
29. Zakarya, D.; Cherqaoui, D.; Esseffar, M.; Villemin, D.; Cense, J. M. Application of Neural Networks to Structure-Sandalwood Odour Relationships. J. Phys. Org. Chem. 1997, 10, 612-622.
30. Ren, J.; Esnouf, R.; Hopkins, A.; Ross, C.; Jones, Y.; Stammers, D.; Stuart, D. The Structure of HIV-1 Reverse Transcriptase Complexed with 9-Chloro-TIBO: Lessons for Inhibitor Design. Structure 1995, 3, 915-926.