(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

Raphaël Frédérick; Frederic Ooms; Neal Castagnoli; Jacques P. Petzer; Jiang Fan Feng; Michael A. Schwarzschild; Cornells J. Van Der Schyf; Johan Wouters

doi:10.1107/S0108270105023140

(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

Raphaël Frédérick, Frederic Ooms, Neal Castagnoli, Jacques P. Petzer, Jiang Fan Feng, Michael A. Schwarzschild, Cornells J. Van Der Schyf, Johan Wouters

Unit of theoretical and structural physico-chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

In the crystal structure of (E)-8-(3-chlorostyryl)-1,3,7- trimethylxanthine (CSC) [systematic name: (E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H- purine-2,6-dione], C ₁₆H ₁₅ClN ₄O ₂, the xanthine ring and the lateral styryl chain are coplanar. The crystal packing involves mainly parallel stacking of these planar molecules. The electrostatic potential calculated on the crystal structure conformation confirms the pharmacophore elements associated with MAO-B inhibition.

Original language	English
Journal	Acta crystallographica. Section C: Crystal structure communications
Volume	61
Issue number	9
DOIs	https://doi.org/10.1107/S0108270105023140
Publication status	Published - 1 Sept 2005

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Frédérick, R., Ooms, F., Castagnoli, N., Petzer, J. P., Feng, J. F., Schwarzschild, M. A., Van Der Schyf, C. J., & Wouters, J. (2005). (E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B. Acta crystallographica. Section C: Crystal structure communications, 61(9). https://doi.org/10.1107/S0108270105023140

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title = "(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B",

abstract = "In the crystal structure of (E)-8-(3-chlorostyryl)-1,3,7- trimethylxanthine (CSC) [systematic name: (E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H- purine-2,6-dione], C 16H 15ClN 4O 2, the xanthine ring and the lateral styryl chain are coplanar. The crystal packing involves mainly parallel stacking of these planar molecules. The electrostatic potential calculated on the crystal structure conformation confirms the pharmacophore elements associated with MAO-B inhibition.",

author = "Rapha{\"e}l Fr{\'e}d{\'e}rick and Frederic Ooms and Neal Castagnoli and Petzer, {Jacques P.} and Feng, {Jiang Fan} and Schwarzschild, {Michael A.} and {Van Der Schyf}, {Cornells J.} and Johan Wouters",

year = "2005",

month = sep,

day = "1",

doi = "10.1107/S0108270105023140",

language = "English",

volume = "61",

journal = "Acta crystallographica. Section C: Crystal structure communications",

issn = "0108-2701",

publisher = "Munksgaard",

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Frédérick, R, Ooms, F, Castagnoli, N, Petzer, JP, Feng, JF, Schwarzschild, MA, Van Der Schyf, CJ & Wouters, J 2005, '(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B', Acta crystallographica. Section C: Crystal structure communications, vol. 61, no. 9. https://doi.org/10.1107/S0108270105023140

(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B. / Frédérick, Raphaël; Ooms, Frederic; Castagnoli, Neal et al.
In: Acta crystallographica. Section C: Crystal structure communications, Vol. 61, No. 9, 01.09.2005.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - (E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

AU - Frédérick, Raphaël

AU - Ooms, Frederic

AU - Castagnoli, Neal

AU - Petzer, Jacques P.

AU - Feng, Jiang Fan

AU - Schwarzschild, Michael A.

AU - Van Der Schyf, Cornells J.

AU - Wouters, Johan

PY - 2005/9/1

Y1 - 2005/9/1

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AB - In the crystal structure of (E)-8-(3-chlorostyryl)-1,3,7- trimethylxanthine (CSC) [systematic name: (E)-8-(3-chlorostyryl)-1,3,7-trimethyl-3,7-dihydro-1H- purine-2,6-dione], C 16H 15ClN 4O 2, the xanthine ring and the lateral styryl chain are coplanar. The crystal packing involves mainly parallel stacking of these planar molecules. The electrostatic potential calculated on the crystal structure conformation confirms the pharmacophore elements associated with MAO-B inhibition.

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M3 - Article

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AN - SCOPUS:30344455384

SN - 0108-2701

VL - 61

JO - Acta crystallographica. Section C: Crystal structure communications

JF - Acta crystallographica. Section C: Crystal structure communications

IS - 9

ER -

(E)-8-(3-Chlorostyryl)-1,3,7-trimethylxanthine, a caffeine derivative acting both as antagonist of adenosine A2A receptors and as inhibitor of MAO-B

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