Theoretical characterization of some amides and esters derivatives of valproic acid

Journal of Molecular Modeling

Volumn 16, Issue 2, 2010, Pages 343-359

  Comelli, Nieves C ^a   Fuentealba, Patricio ^b   Castro, Eduardo A ^a   Jubert, Alicia H ^c  

^a INSTITUTO DE INVESTIGACIONES FISICOQUÍMICAS TEÓRICAS Y APLICADAS INIFTA   (Argentina)

^b UNIVERSITY OF CHILE   (Chile)

^c Centro de Quimica Inorganica   (Argentina)

Author keywords

Antiepileptic drugs; DFT; Electronic delocalization; ELF; Non conventional hydrogen bonds

Indexed keywords

(1 METHYL)PROPYL 2 PROPYLPENTANOATE; 2 BUTANOL VALPROATE; BENZYLVALPROATE; DIMETHYLVALPROMIDE; ISOPENTYL VALPROATE; N (1 PHENYLETHYL) 2 PROPYLPENTANAMIDE; N BENZHYDRYLVALPROMIDE; N ETHYLAMINEVALPROMIDE; N ETHYLVALPROMIDE; N ISOPROPYLVALPROMIDE; PROPYLVALPROATE ESTER; PROPYLVALPROMIDE; UNCLASSIFIED DRUG; VALPROIC ACID; VALPROIC ACID DERIVATIVE; VALPROMIDE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; HYDROGEN BOND; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL;

AMIDES; ANTICONVULSANTS; ENZYME INHIBITORS; ESTERS; HYDROGEN BONDING; MODELS, THEORETICAL; VALPROIC ACID;

EID: 75949090876     PISSN: 16102940     EISSN: 09485023     Source Type: Journal    
DOI: 10.1007/s00894-009-0554-6     Document Type: Article

References (34)

1. HS White 2003 Preclinical development of antiepileptic drugs: past, present, and future directions Epilepsia 44 suppl 7 2 8 10.1046/j.1528-1157.44. s7.10.x 1:CAS:528:DC%2BD3sXnvFOhtL8%3D
2. PE Keane J Simiand E Mendes V Santucci 1983 The effects of analogues of valproic acid on seizures induced by pentylenetetrazol and GABA content in brain of mice Neuropharmacol 22 875 879 10.1016/0028-3908(83)90134-X 1:CAS:528:DyaL3sXkvFyrsLo%3D
3. W Loscher H Nau 1985 Pharmacological evaluation of various metabolites and analogues of valproic acid Anticonvulsant and toxic potencies in mice. Neuropharmacol 24 427 435 1:STN:280:DyaL2M3mvVekug%3D%3D
4. D Lindhout H Meinardi 1984 Spina bifida and in-utero exposure to valproic acid Lancet II 396 10.1016/S0140-6736(84)90557-9
5. E Jager-Roman A Deichl S Jakob A Hartmann S Koch D Rating R Steldinger H Nau H Helge 1986 Fetal growth, major malformations, and minor anomalies in infants born to women receiving valproic acid J Pediatr 108 997 1004 10.1016/S0022-3476(86)80949-0 1:STN:280:DyaL283is1yltg%3D%3D
6. H Nau W Loscher 1986 Pharmacologic evaluation of various metabolites and analogs of valproic acid teratogenic potencies in mice Fundam Appl Toxicol 6 669 676 10.1016/0272-0590(86)90180-6 1:CAS:528:DyaL28XktFOrtrw%3D
7. M Bialer S Hadad B Kadry A Abdul-Hai A Haj-Yehia J Sterling Y Herzig B Yagen 1996 Pharmacokinetic analysis and antiepileptic activity of tetra-methylcyclopropane analogues of valpromide Pharm Res 13 284 289 10.1023/A:1016055517724 1:CAS:528:DyaK28Xht1Oku7o%3D (Pubitemid 26072149)
8. M Bialer 1991 Clinical pharmacology of valpromide Clin Pharmacokinet 20 114 122 10.2165/00003088-199120020-00003 1:STN:280:DyaK3M3jtVyisA%3D%3D
9. A Haj-Yehia M Bialer 1989 Structure-pharmacokinetic relationships in a series of valpromide derivatives with antiepileptic activity Pharm Res 6 682 689 10.1023/A:1015934321764
10. A Haj-Yehia S Hadad M Bialer 1992 Pharmacokinetic analysis of the structural requirements for forming "stable" analogues of valpromide Pharm Res 9 1058 1063 10.1023/A:1015862613315 1:CAS:528:DyaK38XmsVCqsrw%3D
11. O Spiegelstein DL Kroetz RH Levy B Yagen SI Hurst M Levi A Haj-Yehia M Bialer 2000 Structure activity relationship of human microsomal epoxide hydrolase inhibition by amide and acid analogues of valproic acid Pharm Res 17 216 221 10.1023/A:1007577600088 1:CAS:528:DC%2BD3cXitVOqurk%3D (Pubitemid 30158372)
12. S Tasso L Bruno-Blanch G Estiú 2001 Design, synthesis, and anticonvulsant activity of some sulfamides J Mol Model 7 231 239 1:CAS:528:DC%2BD3MXnsF2ktb4%3D
13. S Tasso S Moon L Bruno-Blanch G Estiu 2004 Characterization of the anticonvulsant profile of valpromide derivatives Bioorg Med Chem 12 3857 3869 10.1016/j.bmc.2004.05.003 1:CAS:528:DC%2BD2cXltVKisr4%3D (Pubitemid 38798248)
14. L Gavernet MJ Dominguez Cabrera L Bruno-Blanch G Estiu 2007 Design, synthesis, and anticonvulsant activity of some sulfamides Bioorg Med Chem 15 5604 5614 10.1016/j.bmc.2007.05.024 1:CAS:528:DC%2BD2sXmvV2it7s%3D (Pubitemid 46962986)
15. HyperChem Release 7.5 for Windows. Hypercube, USA, 2002
16. C Peng PY Ayala HB Schlegel MJ Frisch 1996 Using redundant internal coordinates to optimize equilibrium geometries and transition states J Comp Chem 17 49 56 10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0 1:CAS:528:DyaK28XpvFSi
17. Gaussian 03, Revision B.04. Gaussian, Pittsburgh, 2003
18. A Becke 1993 Density-functional thermochemistry III. The role of exact exchange. J Chem Phys 98 5648 5652 1:CAS:528:DyaK3sXisVWgtrw%3D
19. C Lee W Yang R Parr 1988 Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys Rev B 37 785 789 10.1103/PhysRevB.37.785 1:CAS:528:DyaL1cXktFWrtbw%3D
20. Nour S, Krokidis XF, Fuster B, Silvi (1997) TopMod Package, Paris
21. S Noury X Krokidis F Fuster B Silvi 1999 Computational Tools for the Electron Localization Function Topological Analysis Computers and Chemistry 23 597 604 10.1016/S0097-8485(99)00039-X 1:CAS:528:DyaK1MXmvVOrsbs%3D
22. Flükiger P, Lüthi HP, Portmann S, Weber J (2000) MOLEKEL 4.0. Swiss Center for Scientific Computing, Manno
23. A Savin 2005 The electron localization function (ELF) and its relatives: interpretations and difficulties J Mol Struct 727 127 131 1:CAS:528: DC%2BD2MXot1CjtLk%3D
24. AD Becke KE Edgecombe 1990 A simple measure of electron localization in atomic and molecular systems J Chem Phys 92 5397 5403 10.1063/1.458517 1:CAS:528:DyaK3cXisVSlu78%3D
25. B Silvi A Savin 1994 Classification of Chemical bonds based on topological analysis of electron localization functions Nature 371 683 686 10.1038/371683a0 1:CAS:528:DyaK2cXntVyktL4%3D (Pubitemid 24329613)
26. A Savin S Silvi F Colonna 1996 Topological analysis of the electron localization function applied to delocalized bonds Can J Chem 74 1088 1096 10.1139/v96-122 1:CAS:528:DyaK28Xks1yrt7g%3D
27. Gillespie RJ, Hargittai I (1991) The VSEPR Model of Molecular Geometry. Allyn & Bacon, Boston
28. FH Allen O Kennard DG Watson L Brammer AG Orpen R Taylor 1987 Tables of bond lengths determined by X-Ray and neutron diffraction. Part 1. Bond lengths in organic compounds J Chem Soc Perkin Trans II S1 S19
29. Dunitz JD (1995) X -Ray analysis of the structure of Organic Molecules. Verlag Helvetica Chimica Acta, CH-4010 Basel, Switzerland
30. S Berski G Gajewski Z Latajka 2007 Electron localization function (ELF) study on intramolecular delocalization of the electron density in the H2X, H2C=X and XO2 (X = O, S, Se, Te) molecules: Role of the atomic core and lone pair J Mol Struct 844-845 278 285 10.1016/j.molstruc.2007.05.024 (Pubitemid 47576128)
31. Bakhmutov V (2008) Dihydrogen bond: Principles, Experiments, and Applications. Wiley-Interscience, New Jersey
32. Grabowski SJ (2006) Hydrogen Bonding - New Insights. Springer, The Netherlands
33. G Gilli F Bellucci V Ferreti P Gilli 1989 Evidence for resonance-assisted hydrogen bonding from crystal-structure correlations on the enol form of the.beta.-diketone fragment J Am Chem Soc 111 1023 1028 10.1021/ja00185a035 1:CAS:528:DyaL1MXlslSntw%3D%3D
34. M Alikhani F Fuster B Silvi 2005 What can tell the topological analysis of ELF on hydrogen bonding? Struct Chem 16 203 210 10.1007/s11224-005-4451-z 1:CAS:528:DC%2BD2MXmtVWrurw%3D (Pubitemid 41016371)