Browse > Article
http://dx.doi.org/10.13160/ricns.2015.8.3.184

Crystal Structure Analysis of Methyl-3-phenyl-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxylate  

Ganapathy, Jagadeesan (Department of Physics, Presidency College)
Srinivasan, J. (Department of Organic Chemistry, University of Madras, Guindy Campus)
Manickam, Bakthadoss (Department of Organic Chemistry, University of Madras, Guindy Campus)
Publication Information
Journal of Integrative Natural Science / v.8, no.3, 2015 , pp. 184-191 More about this Journal
Abstract
The crystal structure of the potential active methyl-3-phenyl-3H-chromeno[4,3-c]isoxazole-3a(4H)-carboxylate ($C_{18}H_{15}NO_4$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the orthorombic space group $P2_12_12_1$ with unit cell dimension $a=9.8320(17){\AA}$, $b=9.9890(18){\AA}$ and $c=15.588(3){\AA}$ [${\alpha}=90^{\circ}$, ${\beta}=90^{\circ}$ and ${\gamma}=90^{\circ}$]. In the structure chromene, isoxazole and carboxylate are almost coplanar each other. All geometrical parameters revelled that chromene ring of pyran ring adopt sofa conformation. The crystal packing is stabilized by intermolecular C-H...O and C-H...N hydrogen bond interaction.
Keywords
Chromene; Pyran; Single Crystal Structure; X-ray diffraction;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 W . Kemnitzer, S. Jiang, Y. Wang, S. Kasibhatla, C. Crogan-Grundy, and M. Bubenik, "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
2 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", Anticancer Drug Des., Vol. 8, pp. 349-360, 1993.
3 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)", Pestic. Sci., Vol. 22, pp. 41-50, 1998.
4 Q. G. Tang, W. -Y. Wu, W. He, H. -S. Sun, and C. Guo, "Methyl 2-amino-4-(3-fluorophenyl)-4H-benzo [h] chromene-3-carboxylate methanol solvate", Acta Crystallogr E, Vol. 63, pp. o1437-o1438, 2007.   DOI
5 M. Gabor and F. Kallay, "The pharmacology of benzopyrone derivatives and related compounds", Akad Kiado, Budapest, 91-126, 1986.
6 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
7 S. X. Cai, 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
8 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
9 M. Kidwai, S. Saxena, M. K. R. 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
10 J. L. Wang, D. Liu, Z. J. Zhang, S. Shan, X. Han, and S. M. Srinivasula, "Structure-based discovery of an organic compound that binds Bcl-2 protein and induces apoptosis of tumor cells", Proc. Natl. Acad. Sci. U S A, Vol. 97, pp. 7124-7129. 2000.   DOI
11 C. Bruhlmann, F. Ooms, P. A. Carrupt, B. Testa, M. Catto, and F. Leonetti, "Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase", J. Med. Chem., Vol. 44, pp. 3195-3198, 2001.   DOI   ScienceOn
12 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
13 Bruker, APEX2 and SAINT-Plus, Bruker AXS Inc., Madison, 2004.
14 G. M. Sheldrick, SHELXS-97 and SHELXL-97, "Program for crystal Structure solution and refinement", University of Gottingen, Gottingen, 1997.
15 G. M. Sheldrick, "A short history of SHELX", Acta Crystallogr. A, Vol. 64, pp. 112-122, 2008.   DOI   ScienceOn
16 L. J. Farrugia, "ORTEP-3 for Windows—A version of ORTEP-III with a graphical user interface (GUI)", J. Appl. Crystallogr., Vol. 30, p. 565, 1997.
17 A. L. Spek, "Structure validation in chemical crystallography", Acta Crystallogr. D, Vol. 65, pp. 48-155, 2009.   DOI   ScienceOn
18 L. J. Farrugia, "WinGX suite for small-molecule single-crystal crystallography", J. Appl. Crystallogr., Vol. 32, pp. 837-838, 1999.   DOI
19 G. Jagadeesan, G. Sivakumar, M. Bakthadoss, and S. Aravindhan, "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", J. Chosun Natural Sci., Vol. 8, pp. 19-29, 2015.   DOI   ScienceOn