QSAR studies on imidazothienopyrazines as IKK-ß inhibitors: from 2D to 3D

Journal of Chemometrics

Volumn 23, Issue 6, 2009, Pages 304-314

  Long, Wei ^a,b   Liu, Peixun ^b   Li, Xinru ^b   Xu, Yang ^b   Yu, Jie ^b   Ma, Shitang ^b   Yu, Lingling ^a   Zou, Zhongmei ^a  

^a PEKING UNION MEDICAL COLLEGE   (China)

^b INSTITUTE OF RADIATION MEDICINE   (China)

Author keywords

QSAR; IKK inhibitors; imidazothienopyrazines; HM; SVM; Phase

Indexed keywords

BIOACTIVITY; COMPUTATIONAL CHEMISTRY; MOLECULAR GRAPHICS; NONLINEAR SYSTEMS; SUPPORT VECTOR MACHINES;

HEURISTIC METHOD;; IKK-SS INHIBITOR;; IMIDAZOTHIENOPYRAZINE;; PHASE; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;; SUPPORT VECTOR MACHINE;; SUPPORT VECTORS MACHINE; TEST SETS; TRAINING SETS;

HEURISTIC METHODS;

EID: 67649872793     PISSN: 08869383     EISSN: 1099128X     Source Type: Journal    
DOI: 10.1002/cem.1235     Document Type: Article

References (28)

1. Siebenlist U, Franzoso G, Brown K. Structure, regulation and function of NF-kappa B. Annu. Rev. Cell Biol. 1994; 10:405.
2. Burke JR, Wood MK, Ryseck RP, Walther S, Meyers CA. Peptides corresponding to the N and C termini of Ikappaβ-alpha, -beta, and -epsilon as probes of the two catalytic subunits of Ikappaβ kinase, IKK-1 and IKK-2. J. Biol. Chem. 1999; 274:36146.
3. Aupperle KR, Bennett BL, Han Z, Boyle DL, Manning AM, Firestein GSJ. NF-kappa B regulation by I kappa β kinase-2 in rheumatoid arthritis synoviocytes. Immunology 2001; 166:2705.
4. Bonafoux D, Bonar S, Christine L, Clare M, Donnelly A, Guzova J, Kishore N, Lennon P, Libby A, Mathialagan S, McGhee W, Rouw S, Sommers C, Tollefson M, Tripp C, Weier R, Wolfson S, Min Y. Inhibition of IKK-2 by 2-[(aminocarbonyl) amino]-5-acetylenyl-3-thiophenecar-boxamides. Bioorg. Med. Chem. Lett. 2005; 15:2870.
5. Coish PDG, Wickens PL, Lowinger TB. Small molecule inhibitors ofIKK kinase activity. Expert Opin. Ther. Pat. 2006; 16:1.
6. Herrmann O, Baumann B, de Lorenzi R, Muhammad S, Zhang W, Kleesiek J, Malfertheiner M, Kohrmann M, Potrovita I, Maegele I, Beyer C, Burke JR, Hasan MT, Bujard H, Wirth T, Pasparakis M, Schwaninger M. IKK mediates ischemia-induced neuronal death. Nat. Med. 2005; 11:1322-1329.
7. Belema M, Bunker A, Nguyen VN, Beaulieu F, Ouellet C, Qiu Y, Zhang Y, Martel A, Burke JR, McIntyre KW, Pattoli MA, Daloisio C, Gillooly KM, Clarke WJ, Brassil PJ, Zusi FC, Vyas DM. Synthesis and structure-activity relationship of imidazo(1, 2-a)thieno(3, 2-e)pyrazines as IKK-beta inhibitors. Bioorg. Med. Chem. Lett. 2007; 17:4284-4289.
8. Alice B, Daniele P, Patrick D, Anna MB. QSAR study on thiazole and thiadiazole analogues as antagonists for the adenosine A1 and A3 receptors. Bioorg. Med. Chem. 2005; 13:5330.
9. Andrei IK, Igor AS, Mark TQ. Quantitative structure-activity relationships for small non-peptide antagonists of CXCR2: indirect 3D approach using the frontal polygon method. Bioorg. Med. Chem. 2006; 14:352.
10. Li W, Tang Y, Zheng YL, Qiu ZB. Molecular modeling and 3D-QSAR studies of indolomorphinan derivatives as kappa opioid antagonists. Bioorg. Med. Chem. 2006; 14:601.
11. Yao XJ, Liu MC, Zhang XY, Hu ZD, Fan BT. QSAR model for prediction capacity factor of molecular imprinting polymer based on gene expression programming. Anal. Chim. Acta 2002; 462:101-117.
12. Si H, Yuan S, Zhang K, Fu A, Duan Y, Hu Z. Quantitative structure activity relationship study on EC5.0 of anti-HIV drugs. Chemometr. Intell. Lab. 2008; 90:15-24.
13. HyperChem 7.0, Hypercube 2002.
14. Stewart JPP. MOPAC 6.0, Quantum chemistry program exchange, QCPE, No.455, Indiana University, Bloomington, IN, 1989.
15. CODESSA. Comprehensive Descriptors for Structural and Statistical Analysis, Version 2.7.10.
16. Wright JS, Carpenter DJ, McKay DJ. Theoretical calculation of sub-stituent effects on the O-H bond strength of phenolic antioxidants related to vitamin E. J. Am. Chem. Soc. 1985; 107:3902-3909.
17. Katritzky AR, Lobanov VS, Karelson M. Comprehensive Descriptors for Structural and Statistical Analysis, Reference Manual, Version 2.7.10.
18. Katritzky AR, Petrukhin R, Jain R, Karelson M. QSPR analysis of flash points. J. Chem. Inf. Comput. Sci. 2001; 41:1521-1530.
19. Cortes C, Vapnik V. Support-vector networks. Mach. Learn. 1995; 20:273-279.
20. Palm K, Belluardo N, Metsis M, Timmusk T. SAR and QSAR study on 2-aminothiazole derivatives, modulators of transcriptional repression in Huntington's disease. J. Neurosci. 1998; 18:1280.
21. Phase, version 2.5.213; Schrodinger, LLC: New York, 2007.
22. MacroModel, version 9.5.213; Schrodinger, LLC: New York, 2007.
23. Sannigrahi AB. Ab-initio molecular-orbital calculations of bond index and valency. Adv. Quant. Chem. 1992; 23:301-3351.
24. Basak SC, Harriss DK, Magnuson VR. Comparative study of lipophilicity versus topological molecular descriptors in biological correlations. J. Pharm. Sci. 1984; 73:429.
25. Rohrbaugh RH, Jurs PC. Molecular shape and the prediction of high-performance liquid chromatographic retention indexes of polycyclic aromatic hydrocarbons. Anal. Chem. 1987; 59:1048.
26. Rohrbaugh RH, Jurs PC. Descriptions of molecular shape applied in studies of structure activity and structure/property relationships. Anal. Chim. Acta 1987; 199:99.
27. Zefirov NS, Kirpichenok MA, Izmailov FF, Trofimov MI. Calculation schemes for atomic electronegativities in molecular graphs within the framework of sanderson principle. Dokl. Akad. Nauk SSSR 1987; 296:883.
28. Kirpichenok MA, Zefirov NS. Electronegativity and geometry of molecules. 1. Principles of developed approach and analysis of the effect of nearest electrostatic interactions on the bond length in organic-molecules. Zh. Org. Khim. 1987; 23:4.