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Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin
Masaki Ichitani (1)
, Soh-ichi Kitoh (2) , Keiko Tanaka (3) , Shuhei Fujinami (4) , Mitsuhiro Suda (5) , Mitsunori Honda (6) , Ko-Ki Kunimoto (7,*) (1) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(2) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(3) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(4) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(5) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(6) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(7) Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
(*) Corresponding Author
Received: 25 Sep 2013, Accepted: 06 Oct 2013, Published: 31 Mar 2014
Abstract
Crystal structures of racemic and enantiomeric 5-isopropyl-5-methylhydantoin (IPrMH) have been determined by single crystal X-ray diffraction. Melting temperatures and solid state infrared spectra are also measured. Racemic IPrMH has a lower melting temperature than the pure enantiomer by 25 °C. The infrared spectrum of racemic IPrMH is identical with that of the pure enantiomer. Nevertheless, the racemic IPrMH doesn’t crystallize as a conglomerate but as a racemic compound. The racemic and the enantiomeric crystals are very similar to each other in molecular geometries and intermolecular interactions. In the both cases, the molecules are connected via N−H···O hydrogen bonds to form R22(8) rings, and these rings are linked into infinite one-dimensional tapes. In the racemic crystal, a single tape is composed of single enantiomer and itself is homochiral.
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DOI: 10.5155/eurjchem.5.1.6-10.933
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References
[1]. Mutschler, E.; Derendorf, H. Drug Actions, Basic Principles and Therapeutic Aspects, Medpharm Scientific Publishers, Stuttgart, 1995.
[2]. Knabe, J.; Baldauf, J.; Ahlhem, A. Pharmazie 1997, 52, 912-919.
[3]. Dylag, T.; Zygmunt, M.; Maciag, D.; Handzlik, J.; Bednarski, M.; Filipek, B.; Kiec-Kononowicz, K. Eur. J. Med. Chem. 2004, 39, 1013-1027.
http://dx.doi.org/10.1016/j.ejmech.2004.05.008
[4]. Opacic, N.; Barbaric, M.; Zorc, B.; Cetina, M.; Nagl, A.; Frkovic, D.; Kralj, M.; Pavelic, K.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Raic-Malic, S.; Mintas, M. J. Med. Chem. 2005, 48, 475-482.
http://dx.doi.org/10.1021/jm040869i
[5]. Lattmann, E.; Ayuko, W. O.; Kinchinaton, D.; Langley, C. A.; Singh, H.; Karimi, L.; Tisdale, M. J. J. Phar. Pharmacol. 2003, 55, 1259-1265.
http://dx.doi.org/10.1211/0022357021756
[6]. Carmi, C.; Cavazzoni, A.; Zuliani, V.; Lodola, A.; Bordi, F.; Plazzi, P. V.; Alfieri, R. R.; Petronini, P. G.; Mor, M. Bioorg. Med. Chem. Lett. 2006, 16, 4021-4025.
http://dx.doi.org/10.1016/j.bmcl.2006.05.010
[7]. Singh, G.; Driever, P. H.; Sander, J. W. Brain 2005, 128, 7-17.
http://dx.doi.org/10.1093/brain/awh363
[8]. Kaindl, A. M.; Asimiadou, S.; Manthey, D.; Hagen, M. V.; Turski, L.; Ikonomidou, C. Cell. Mol. Life Sci. 2006, 63, 399-413.
http://dx.doi.org/10.1007/s00018-005-5348-0
[9]. Tompkins, J. E. J. Med. Chem. 1986, 29, 855-859.
http://dx.doi.org/10.1021/jm00155a042
[10]. Takahashi, A.; Matsuoka, H.; Yamada, K.; Uda, Y. Food Chem. Toxicol. 2005, 43, 521-528.
http://dx.doi.org/10.1016/j.fct.2004.12.005
[11]. Al-Madi, S. H.; Al-Obaid, A. M.; El-Subbagh, H. I. Anti-Cancer Drugs 2001, 12, 835-839.
http://dx.doi.org/10.1097/00001813-200111000-00007
[12]. Shiozaki, M. Carbohyd. Res. 2002, 337, 2077-2088.
http://dx.doi.org/10.1016/S0008-6215(02)00217-3
[13]. Marton, J.; Enisz, J.; Hosztafi, S.; Timar, T. J. Agric. Food. Chem. 1993, 41, 148-152.
http://dx.doi.org/10.1021/jf00025a031
[14]. Jha, S.; Silversides, J. D.; Boyle, R. W.; Archibald, S. J. Cryst. Eng. Comm. 2010, 12, 1730-1739.
http://dx.doi.org/10.1039/b924683e
[15]. Cruz-Cabeza, A. J.; Schwalbe, C. H. New J. Chem. 2012, 36, 1347-1354.
http://dx.doi.org/10.1039/c2nj21060f
[16]. Ogawa, T.; Kitoh, S.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x199-x200.
http://dx.doi.org/10.2116/analscix.23.x199
[17]. Ogawa, T.; Kitoh, S.; Okagawa, M.; Ichitani, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2007, 23, x201-x202.
http://dx.doi.org/10.2116/analscix.23.x201
[18]. Kunimoto, K.; Ichitani, M.; Ogawa, T.; Kitoh, S.; Kuwae, A.; Hanai, K. Spectrosc. Lett. 2009, 42, 73-80.
http://dx.doi.org/10.1080/00387010802428575
[19]. Ogawa, T.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 91-92.
[20]. Taniguchi, K.; Okumura, H.; Honda, M.; Suda, M.; Fujinami, S.; Kuwae, A.; Hanai, K.; Maeda, S.; Kunimoto, K. Anal. Sci. X-ray Struct. Anal. Online 2009, 25, 93-94.
[21]. Ichitani, M.; Kitoh, S.; Fujinami, S.; Suda, M.; Honda, M.; Kunimoto, K. Acta Cryst. E 2013, 69, o953-o953.
http://dx.doi.org/10.1107/S1600536813013639
[22]. Ichitani, M.; Kitoh, S.; Tanaka, K.; Fujinami, S.; Suda, M.; Honda, M.; Kuwae, A.; Hanai, K.; Kunimoto, K. Eur. J. Chem. 2013, 4, 350-352.
http://dx.doi.org/10.5155/eurjchem.4.4.350-352.872
[23]. Rigaku CrystalClear, Rigaku Corporation, Tokyo, Japan, 2006.
[24]. Rigaku REQAB, Rigaku Corporation, Tokyo, Japan, 1998.
[25]. Burla, M. C.; Caliandro, R.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; De Caro, L.; Giacovazzo, C.; Polidori, G.; Siliqi, D.; Spagna, R. J. Appl. Cryst. 2007, 40, 609-613.
http://dx.doi.org/10.1107/S0021889807010941
[26]. Sheldrick, G. M. Acta Cryst. A 2008, 64, 112-122.
http://dx.doi.org/10.1107/S0108767307043930
[27]. Rigaku CrystalStructure, Rigaku Corporation, Tokyo, Japan, 2010.
[28]. Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739-750.
http://dx.doi.org/10.3390/11100739
[29]. Farrugia, L. J. J. Appl. Cryst. 2012, 45, 849-854.
http://dx.doi.org/10.1107/S0021889812029111
[30]. Macrae, C. F.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Shields, G. P.; Taylor, R.; Towler, M.; van de Streek, J. J. Appl. Cryst. 2006, 39, 453-457.
http://dx.doi.org/10.1107/S002188980600731X
[31]. Mitchell, A. G. J. Pharm. Pharmaceut. Sci. 1998, 1, 8-12.
[32]. Wilhoit, R. C.; Chan, J.; Hall, K. R. J. Phys. Chem. Ref. Data 1985, 14, 1-175.
http://dx.doi.org/10.1063/1.555747
[33]. Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
http://dx.doi.org/10.1021/ar00172a005
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