X-ray crystallographic and theoretical studies of an anticonvulsant enaminone: Methyl 4-(4′-bromophenyl)amino-6-methyl-2-oxocyclohex-3-en-1- oate

Medical Principles and Practice

Volumn 12, Issue 4, 2003, Pages 237-242

  Edafiogho, I O ^a   Denny, B J ^a   Schwalbe, C H ^b   Lowe, P R ^b  

^a KUWAIT UNIVERSITY   (Kuwait)

^b ASTON UNIVERSITY   (United Kingdom)

Author keywords

Ab initio quantum mechanics; Anticonvulsant enaminone; X ray structure

Indexed keywords

ANTICONVULSIVE AGENT; CARBON; CYCLOHEXENE DERIVATIVE; E 139; ENAMINONE METHYL 4 (4' BROMOPHENYL)AMINO 6 METHYL 2 OXOCYCLOHEX 3 EN 1 OATE; NITROGEN; OXYGEN; UNCLASSIFIED DRUG;

AB INITIO CALCULATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG CONFORMATION; DRUG POTENCY; DRUG STRUCTURE; ENANTIOMER; ENERGY; GEOMETRY; MOLECULE; MOUSE; NONHUMAN; PHARMACOPHORE; RAT; SEIZURE; THEORETICAL STUDY; X RAY CRYSTALLOGRAPHY;

ANTICONVULSANTS; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0345168178     PISSN: 10117571     EISSN: None     Source Type: Journal    
DOI: 10.1159/000072290     Document Type: Article

References (18)

1. Cholli AL, Lau ML, Gala K: Necessary conditions for the pi-electron delocalization of enamino-type muscle relaxants. J Pharm Sci 1993; 82:1275-1280.
2. Dannhardt G, Dominiak P, Laufer S: Hypertensive effects and structure-activity relationships of 5-omega-aminoalkyl isoxazoles. Arzneimittelforschung 1993;43:441-444.
3. Patzel M, Liebscher J: Ring transformation with bridged 1,3-dicarbonyl heteroanalogues, III: 5-(omega-aminoalkyl)-1,2,4-oxadiazoles by ring-transformations of 3-methylthio-2-aza-3-propeniminium salts. Arch Pharm (Weinheim) 1991;324:963-965.
4. Dominguez JN, Lopez S, Charris J, Iarruso L, Lobo G, Semenov A, Olsen JE, Rosenthal PJ: Synthesis and antimalarial effects of phenothiazine inhibitors of a Plasmodium falciparum cysteine protease. J Med Chem 1997;40:2726-2732.
5. Edafiogho IO, Moore JA, Farrar VA, Nicholson JM, Scott KR: Synthesis, reactions and preliminary evaluations of enaminone esters. J Pharm Sci 1994;83:79-84.
6. Eddington ND, Cox DS, Roberts RR, Stables JP, Powell CB, Scott KR: Enaminones - versatile therapeutic pharmacophores: Further advances. Curr Med Chem 2000;7:417-436.
7. Scott KR, Edafiogho IO, Richardson EL, Farrar VA, Moore JA, Teitz EI, Hinko CN, Chang H, El-Assadi A, Nicholson JM: Synthesis and anticonvulsant activity of enaminones. 2. Further structure-activity correlations. J Med Chem 1993;36:1947-1955.
8. Edafiogho IO, Moore JA, Alexander MS, Scott KR: Nuclear magnetic resonance studies of anticonvulsant enaminones. J Pharm Sci 1994;83:1155-1170.
9. Sheldrick GM: SHELXL, a Program for the Refinement of Crystal Structures. Göttingen, University of Göttingen, 1997.
10. Johnson CK: ORTEP. Report ORNL-5138. Oak Ridge, Oak Ridge National Laboratory, 1976.
11. Schmidt MW, Baldridge KK, Boatz JA, Elbert ST, Gordan MS, Jensen JH, Koseki S, Matsunaga N, Nguyen KA, Su SJ, Windus TL, Dupuis M, Montgomery JA: General atomic and molecular electronic-structure system. J Comput Chem 1993;14:1347-1363.
12. CHEM-X from Oxford Molecular Ltd, a subsidiary of Pharmacopoeia.
13. Foster JE, Nicholson JM, Butcher R, Stables JP, Edafiogho IO, Goodwin AM, Henson MC, Smith CA, Scott KR: Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants. Bioorg Med Chem 1999;7:2415-2425.
14. Bertolasi V, Gilli P, Ferretti V, Gilli G: Intermolecular N-H...O hydrogen bonding assisted by resonance. II. Self-assembly of hydrogen-bonded secondary enaminones in supramolecular catemers. Acta Crystallogr B 1998;54:50-65.
15. 3. Acta Crystallogr C 1993;49:2045-2046.
16. ConQuest from the Cambridge Crystallographic Data Centre, Cambridge, 2000
17. Dimmock JR, Vashishtha SC, Stables JP: Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarba-zones derived from aromatic and unsaturated carbonyl compounds. Eur J Med Chem 2000;35:241-248.
18. Pandeya SN, Yogeeswari P, Stables JP: Synthesis and anticonvulsant activity of 4-bromophenyl substituted aryl semicarbazones. Eur J Med Chem 2000;35:879-886.