Elucidation of the absolute configuration of JNJ-27553292, a CCR2 receptor antagonist, by vibrational circular dichroism analysis of two precursors

Chirality

Volumn 18, Issue 8, 2006, Pages 609-620

  Kuppens, Tom ^a   Herrebout, Wouter ^b   Van Der Veken, Benjamin ^b   Corens, David ^c   De Groot, Alex ^c   Doyon, Julien ^c   Van Lommen, Guy ^c   Bultinck, Patrick ^a,d  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF ANTWERP   (Belgium)

^c JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^d Department of Inorganic and Physical Chemistry ^*  (Belgium)

Author keywords

Absolute configuration; CCR 2 antagonists; Chiral; Conformations; DFT; Inflammatory diseases; Infrared; Vibrational circular dichroism; Vibrational spectra

Indexed keywords

1 (3',4' DICHLOROPHENYL)PROPANAMINE; 1 (3',4' DICHLOROPHENYL)PROPANOL; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR2; IMIDAZOLE DERIVATIVE; JNJ 27553292; PROPANE; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DIPOLE; DRUG CONFORMATION; DRUG STRUCTURE; GEOMETRY; INFLAMMATORY DISEASE; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; STEREOSPECIFICITY; STRUCTURE ANALYSIS; VIBRATION; VIBRATIONAL CIRCULAR DICHROISM;

CIRCULAR DICHROISM; COMPUTER SIMULATION; ETHYLENETHIOUREA; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PRODRUGS; RECEPTORS, CHEMOKINE; ROTATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 33748754065     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20297     Document Type: Article

References (36)

1. Dawson J, Miltz W, Mir AK, Wiessner C. Targeting monocyte chemoattractant protein-1 signalling in disease. Expert Opinion on Therapeutic Targets 2003;7:35-48.
2. Van Lommen G, Doyon J, Coesemans E, Boeckx S, Cools M, Buntinx M, Hermans B, VanWauwe J. 2-mercaptoimidazoles, a new class of potent CCR2 antagonists. Bioorg Med Chem Lett 2005;15:497-500.
3. Thompson AS, Humphrey GR, Demarco AM, Mathre DJ, Grabowski EJJ. Direct conversion of activated alcohols to azides using diphenyl phosphorazidate: a practical alternative to mitsunobu conditions. J Org Chem 1993;58:5886-5888.
4. Yoshioka M, Kawakita T, Ohno M. Asymmetric induction catalyzed by conjugate bases of chiral proton acids as ligands - enantioselective addition of dialkylzinc-orthotitanate complex to benzaldehyde with catalytic ability of a remarkable high order. Tetrahedron Lett 1989;30:1657-1660.
5. Kitamura M, Suga S, Kawai K, Noyori R. Catalytic asymmetric induction: highly enantioselective addition of dialkylzincs to aldehydes. J Am Chem Soc 1986;108:6071-6072.
6. Stephens PJ, Devlin FJ. Determination of the structure of chiral molecules using ab initio vibrational circular dichroism spectroscopy. Chirality 2000;12:172-179.
7. Stephens PJ. Vibrational circular dichroism spectroscopy: A new tool for the stereochemical characterization of chiral molecules. In: Bultinck P, De Winter H, Langenaeker W, Tollenaere JP, editors. Computational medicinal chemistry for drugs discovery. New York: Marcel Dekker, Inc.; 2004. p 699-725.
8. Berova N, Nakanishi K, Woody RW. Circular Dichroism: Principles and Applications. New York: Wiley-VCH; 2000.
9. Holzwart G, Hsu EC, Mosher HS, Faulkner TR, Moscowit A. Infrared circular-dichroism of carbon-hydrogen and carbon-deuterium stretching modes: observations. J Am Chem Soc 1974;96:251-252.
10. Nafie LA, Keiderling TA, Stephens PJ. Vibrational circular-dichroism. J Am Chem Soc 1976;98:2715-2723.
11. Freedman TB, Cao XL, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758.
12. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ. Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996;252:211-220.
13. Devlin FJ, Stephens PJ, Cheeseman JR, Frisch MJ. Ab initio prediction of vibrational absorption and circular dichroism spectra of chiral natural products using density functional theory: alpha-pinene. J Phys Chem A 1997;101:9912-9924.
14. Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ. Ab-initio calculation of vibrational absorption and circular-dichroism spectra using density-functional force-fields. J Phys Chem US 1994;98:11623-11627.
15. Ayers PW, Yang W. Density-functional theory. In: Bultinck P, De Winter H, Langenaeker W, Tollenaere JP, editors. Computational medicinal chemistry for drugs discovery. New York: Marcel Dekker, Inc.; 2004. p 89-118.
16. Kuppens T, Bultinck P, Langenaeker W. Determination of absolute configuration via vibrational circular dichroism. Drug Discovery Today. Technologies 2004;1:269-275.
17. Urbanova M, Setnicka V, Volka K. Measurements of concentration dependence and enantiomeric purity of terpene solutions as a test of a new commercial VCD spectrometer. Chirality 2000;12:199-203.
18. Nafie LA. Dual polarization modulation: A real-time, spectral-multiplex separation of circular dichroism from linear birefringence spectral intensities. Appl Spectrosc 2000;54(11):1634-1645.
19. Kuppens T, Vandyck K, Van der Eycken J, Herrebout W, van der Veken BJ, Bultinck P. Determination of the Absolute Configuration of three as-hydrindacene compounds by Vibrational Circular Dichroism. J Org Chem 2005;70:9103-9114.
20. Setnicka V, Urbanova M, Bour P, Kral V, Volka K. Vibrational circular dichroism of 1,1′-binaphthyl derivatives: Experimental and theoretical study. J Phys Chem A 2001;105:8931-8938.
21. Gaussian03, version Revision B.05; Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery Jr JA, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA. Wallingford, CT: Gaussian, Inc.; 2004.
22. Becke AD. Density-functional thermochemistry. 3. The role of exact exchange. J Chem Phys 1993;98:5648-5652.
23. Lee CT, Yang WT, Parr RG. Development of the colle-salvetti correlation-energy formula into a functional of the electron-density. Phys Rev B 1988;37:785-789.
24. Kuppens T, Langenaeker W, Tollenaere JP, Bultinck P. Determination of the stereochemistry of 3-hydroxymethyl-2,3-dihydro-[1,4]dioxino[2,3·b] pyridine by vibrational circular dichroism and the effect of DFT integration grids. J Phys Chem A 2003;107:542-553.
25. Hehre WJ, Radom L, Schleyer PR, Pople JA. Ab initio molecular orbital theory. New York: Wiley; 1986.
26. Sadowski J, Schwab CH, Gasteiger J. 3D structure generation and conformational searching. In: Bultinck P, De Winter H, Langenaeker W, Tollenaere JP, editors. Computational medicinal chemistry for drugs discovery. New York: Marcel Dekker, Inc.; 2004. p 151-212.
27. Woon DE, Dunning TH. Gaussian-basis sets for use in correlated molecular calculations. 3. The atoms aluminum through argon. J Chem Phys 1993;98:1358-1371.
28. Kendall RA, Dunning TH, Harrison RJ. Electron-affinities of the 1st-row atoms revisited - systematic basis-sets and wave-functions. J Chem Phys 1992;96:6796-6806.
29. Ditchfield R. Self-consistent perturbation-theory of diamagnetism. 1. Gauge-invariant lcao method for NMR chemical-shifts. Mol Phys 1974;27:789-807.
30. Stephens PJ. Gauge dependence of vibrational magnetic dipole transition moments and rotational strengths. J Phys Chem US 1987;91: 1712-1715.
31. McQuarrie DA. Statistical Thermodynamics. New York: Harper and Row; 1973.
32. Polavarapu PL. New spectroscopic tool - absolute-configuration determination of pharmaceutical compounds by vibrational circular-dichroism. Spectroscopy 1994;9:48-55.
33. Rauk A. Vibrational circular dichroism intensities: ab initio calculations. In: Mezey PG, editor. New developments in molecular chirality. Boston: Kluwer Academic Publishers; 1991. p 57-92.
34. Schellman JA. Circular-dichroism and optical-rotation. Chem Rev 1975;75:323-331.
35. Scott AP, Radom L. Harmonic vibrational frequencies: An evaluation of Hartree-Fock, Moller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J Phys Chem US 1996;100:16502-16513.
36. Wong MW. Vibrational frequency prediction using density functional theory. Chem Phys Lett 1996;256:391-399.