Browse > Article
http://dx.doi.org/10.13160/ricns.2015.8.1.19

Crystal Structure Theory and Applications of 14-Ethoxy-4,6,-dimethyl-8.12- dioxa-4.6-diazatetracyclo [8.8.0.02,7.013,18]octadeca-13,15,17-triene-3,5-dione  

Ganapathy, Jagadeesan (Department of Physics, Presidency College)
Sivakumar, G. (Department of Organic Chemistry, University of Madras, Guindy Campus)
Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras, Guindy Campus)
Sanmargam, Aravindhan (Department of Physics, Presidency College)
Publication Information
Journal of Integrative Natural Science / v.8, no.1, 2015 , pp. 19-29 More about this Journal
Abstract
In view of the growing medicinal importance of chromene and its derivatives, the single crystal X-ray diffraction study was carried out for the potential active 4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo [8.8.0.02,7.013,18]octadeca-2(7),13,15,17-tetraene-3,5,11-trione-2-ethoxyphenyl (2E)-but-2-enoate ($C_{18}H_{20}N_2O_5$). In the title compound are two molecules exist in the asymmetric unit. It crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=14.608(3) ${\AA}$, b=12.845(3) and c= 17.781(4) [alpha & gamma=$90^{\circ}$ beta=$91.233(5)^{\circ}$]. Both pyran and pyran ring of the chromene moiety adopts sofa conformation in the molecule A & B. The crystal structure is stabilized by intramolecular C-H...O hydrogen bond interaction.
Keywords
Pyran; Chromene; Sofa Conformation; Single Crystal Structure; X-ray Diffraction (XRD);
Citations & Related Records
연도 인용수 순위
  • Reference
1 G. T. Brooks, A. P. Ottridge, and D. W. Mace, "The effect of some furochromene and benzochromene analogues of 2,2-dimethyl-7-methoxychromene (precocene I) and benzofuran precursors on Oncopeltus fasciatus (dallas) and Locusta migratoria migratorioides (R&F)", Pest Manag. Sci., Vol. 22, pp. 41-50, 1988.   DOI   ScienceOn
2 C. Bruhlmann, F. Ooms, P. A. Carrupt, B. Testa, M. Catto, F. Leonetti, C. Altomare, and A. Carotti, "Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase", J. Med. Chem., Vol. 44, pp. 3195-3198, 2001.   DOI   ScienceOn
3 S. X. Cai, "Small molecule vascular disrupting agents: potential new drugs for cancer treatment", Recent Pat. Anti-Canc., Vol. 2, pp. 79-101, 2007.   DOI   ScienceOn
4 C. S. Xiong, J. Drewe, and S. Kasibhatla, "A chemical genetics approach for the discovery of apoptosis inducers: from phenotypic cell based HTS assay and structure-activity relationship studies, to identification of potential anticancer agents and molecular targets", Curr. Med. Chem., Vol. 13, pp. 2627-2644, 2006.   DOI   ScienceOn
5 S. X. Cai, J. Drewe, and W. Kemnitzer, "Discovery of 4-aryl-4H-chromenes as potent apoptosis inducers using a cell- and caspase-based Anti-cancer Screening Apoptosis Program (ASAP): SAR studies and the identification of novel vascular disrupting agents", Anti-Cancer Agent. Me., Vol. 9, pp. 437-456, 2009.   DOI
6 G. P. Ellis, "The chemistry of heterocyclic compounds", John Wiley and Sons Inc, New York, 1997.
7 M. Gabor and F. Kallay, "The pharmacology of benzopyrone derivatives and related compounds", Akademiai Kiado, pp. 91-126, 1986.
8 A. Hassanabadi, M. H. Mosslemin, M. Anary-Abbasinejad, and M. Ghasemi, "One-pot synthesis of substituted 4H-chromenes by three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and N-aryl-3-hydroxynaphthalene-2-carboxamide", Synthetic Commun., Vol. 41, pp. 3714-3719, 2011.   DOI   ScienceOn
9 W. Kemnitzera, S. Jianga, Y. Wanga, S. Kasibhatlaa, C. Crogan-Grundya, M. Bubenikb, D. Labrecqueb, R. Denisb, S. Lamotheb, G. Attardob, H. Gourdeaub, B. Tsenga, J. Drewea, and S. X. Cai "Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based HTS assay. Part 5: modifications of the 2- and 3-positions", Bioorg. Med. Chem. Lett., Vol. 18, pp. 603-607, 2008.   DOI   ScienceOn
10 S. R. Kesten, T. G. Heffner, S. J. Johnson, T. A. Pugsley, J. L. Wright, and L. D. Wise, "Design, synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists", J. Med. Chem., Vol. 42, pp. 3718-3725, 1999.   DOI   ScienceOn
11 M. Kidwai, S. Saxena, M. K. Rahman Khan, and S. S. Thukral, "Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents", Bioorg. Med. Chem. Lett., Vol. 15, pp. 4295-4298, 2005.   DOI   ScienceOn
12 Bruker, "APEX2 and SAINT-Plus", Bruker AXS Inc., Madison, 2004.
13 Q.-G. Tang, W.-Y Wu, W. He, H.-S. Sun, and C. Guo, "Methyl 2-amino-4-(3-fluoro-phen-yl)-4Hbenzo[ h]chromene-3-carboxyl-ate methanol solvate", Acta Crystallogr. E, Vol. 63, pp. o1437-o1438, 2007.   DOI
14 P. Valenti, P. Da Re, A. Rampa, P. Montanari, M. Carrara, and L. Cima, "Benzo-gamma-pyrone analogues of geiparvarin: synthesis and biological evaluation against B16 melanoma cells", Anti-Cancer Drug Design, Vol. 8, pp. 349-360, 1993.
15 J.-L. Wang, D. Liu, Z.-J. Zhang, S. Shan, X. Han, S. M. Srinivasula, C. M. Croce, E. S. Alnemri, and Z. Huang, "Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells", P. Natl. Acad. Sci. USA., Vol. 97, pp. 7124-7129, 2000.   DOI
16 G. M. Sheldrick, "SHELXS-97 and SHELXL-97, Program for Crystal Structure Solution and Refinement", University of Gottingen, Gottingen, Germary, 1997.
17 G. M. Sheldrick, "A short history of SHELX", Acta Crystallogr. A, Vol. 64, pp. 112-122, 2008.   DOI   ScienceOn
18 L. J. Farrugia, "ORTEP-3 for Windows-A version of ORTEP-III with a graphical user interface (GUI)", J. Appl. Crystallogr., Vol. 30, pp. 565, 1997.
19 A. L. Spek, "Structure validation in chemical crystallography", Acta Crystallogr. D, Vol. 65, pp. 148-155, 2009.   DOI   ScienceOn
20 L. J. Farrugia, "WinGX Suite for small-molecule single-crystal crystallography", J. Appl. Crystallogr., Vol. 32, pp. 837-838, 1999.   DOI