HPLC enantioseparation and absolute configuration of novel anti-inflammatory pyrrole derivatives

Chirality

Volumn 20, Issue 6, 2008, Pages 775-780

  Biava, Mariangela ^a   Cirilli, Roberto ^b   Fares, Vincenzo ^c   Ferretti, Rosella ^b   Gallinella, Bruno ^b   La Torre, Francesco ^b   Poce, Giovanna ^a   Porretta, Giulio Cesare ^a   Supino, Sibilla ^a   Villani, Claudio ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^c CNR   (Italy)

Author keywords

Absolute configuration; Anti inflammatory pyrrole derivatives; Chiralpak IA; Chiroptical properties; Polysaccharide based chiral stationary phases; Semipreparative scale enantioseparation; Stereoselective HPLC

Indexed keywords

ANTIINFLAMMATORY AGENT; PYRROLE DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT;

ANALYTIC METHOD; ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OPTICAL ROTATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ISOLATION AND PURIFICATION; METHODOLOGY; STEREOISOMERISM; ULTRAVIOLET SPECTROPHOTOMETRY;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PYRROLES; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 45849083178     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20518     Document Type: Article

References (17)

1. Federsel HJ. Facing chirality in the 21st century: approaching the challenges in the pharmaceutical industry. Chirality 2003;15:S128-S142.
2. Cerè V, Peri F, Pollicino S, Ricci A, Devlin FJ, Shephens PH, Gasparrini F, Rompietti R, Villani C. Synthesis, chromatographic separation, vibrational circular dichroism spectroscopy, and ab initio DFT studies of chiral thiepane tetraol derivatives. J Org Chem 2005;70:664-669.
3. Huang X, Nakanishi K, Berova N. Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies. Chirality 2000;12:237-255.
4. Polavarapu PL. Optical rotation: recent advances in determining the absolute configuration. Chirality 2002;14:768-781.
5. Ohno A, Kunitomo J, Kawai Y. Physical properties of Atropisomeric 5-deazaflavin derivatives. Tetrahedron 1997;53:4601-4610.
6. Mattheews JM, Dyatkin AB, Evangelisto M, Gauthier DA, Hecker LR, Hoekstra WJ, Liu F, Poulter BL, Sorgi KL, Maryanoff BE. Synthesis, resolution, and absolute configuration of novel tricyclic benzodiazepines. Tetrahedron; Asymmetry 2004;15:1259-1267.
7. Cirilli R, Ferretti R, Gallinella B, Turchetto L, Bolasco A, Secci D, Chimenti P, Pierini M, Fares V, Befani O, La Torre F. Enantiomers of C(5)-chiral l-acetyl-3,5-dipheny1-5,5-dihydro-(lH)-pyrazole derivatives: analytical and semipreparative HPLC separation, chiroptical properties, absolute configuration, and inhibitory activity against monoamine oxidase. Chirality 2004;16:625-636.
8. Pirkle WH, Hoover DJ. NMR chiral solvating agents. Top Stereochem 1982;13:263-331.
9. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer regents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and .alpha.-methoxy-.alpha.- trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
10. Seco JM, Quiñoá E, Riguera R The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117.
11. Zang T, Kentzy C, Franco P, Ohnishi A Kagamihara Y, Kurosawa H. Solvent versatility of immobilized 3,Mimethylphenylcarbamate of amylose in enantiomeric separations by HPLC. J Chromatogr A 2005;1075:65-75.
12. Di Bari L, Pescitelli G, Salvadori P, Rovini M, Anzini M, Cappelli A, Vomero S. Synthesis, resolution, and absolute configuration of two novel and selective cyclooxygenase-2 inhibitors based on the 1,5-diar-ylpyrrole structure. Tetrahedron: Asymmetry 2006;17:3430-3436.
13. Burla MC, Calandro R, Cavalli M, Carrozzini B, Cascarano GL, De Caro L, Giacovazzo C, Polidori G, Spagna R. SIR2004: An improved tool for crystal structure determination and refinement J Appl Crystallogr 2005;38:381-388.
14. Flack HD. On enantiomorph-polarity estimation. Acta Cryst 1983:76-881.
15. Cirilli R, Orlando V, Ferretti R, Turchetto L, Silvestri R, De Martino G, La Torre F. Chirality 2006;18:621-632.
16. Cirilli R, Simonelli A, Ferretti R, Bolasco A, Chimenti P, Secci D, Maccioni E, La Torre F. Analytical and semipreparative high performance liquid chromatography enantioseparation of new substituted 1-thiocar-bamoyl-3,5-diaryl- 4,5-dihydro-(1H)-pyrazoles on polysaccharide-based chiral stationary phases in normal-phase, polar organic and reversed-phase conditions. J Chromatogr A 2006;1101:198-203.
17. Gasparrini F, Misiti D, Rompietti R, Villani C. New hybrid polymeric liquid chromatography chiral stationary phase prepared by surface-initiated polymerization. J Chromatogr A 2005;1064:25-38.