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Synthesis and X-ray diffraction data of 2-ethyl-6-(pyridin-4-yl)-7H-indeno[2,1-c]quinoline

Published online by Cambridge University Press:  10 October 2013

H.A. Camargo ,
A. Sánchez ,
J.A. Henao ,
Arnold R. Romero Bohórquez  and
Vladimir V. Kouznetsov
H.A. Camargo
Affiliation:
Grupo de Investigación en Nuevos Materiales y Energías Alternativas (GINMEA), Facultad de Química Ambiental, Universidad Santo Tomás, Campus Universitario Floridablanca, Santander, Colombia
A. Sánchez
Affiliation:
Grupo de Investigación en Nuevos Materiales y Energías Alternativas (GINMEA), Facultad de Química Ambiental, Universidad Santo Tomás, Campus Universitario Floridablanca, Santander, Colombia
J.A. Henao*
Affiliation:
Grupo de Investigación en Química Estructural (GIQUE), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
Arnold R. Romero Bohórquez
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
Vladimir V. Kouznetsov
Affiliation:
Laboratorio de Química Orgánica y Biomolecular (LQOBio), Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, A.A. 678, Carrera 27, Calle 9 Ciudadela Universitaria. Bucaramanga, Colombia
*
a) Author to whom correspondence should be addressed. Electronic mail: [email protected]
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Abstract

The compound 2-ethyl-6-(pyridin-4-yl)-7H-indeno[2,1-c]quinoline (2) (chemical formula C23H22N2) was synthesized through the free-solvent oxidation reaction mediated by elemental sulfur from the corresponding 2-ethyl-6-(pyridin-4-yl)-5,6,6a,11b-tetrahidro-7H-indeno[2,1-c]quinoline (1), an adduct easily obtained, using the Lewis acid-promoted [4 + 2] cycloaddition reaction. Preliminary molecular characterization was performed by Fourier transform-infrared and gas chromatography-mass spectrometry. The X-ray powder diffraction (XRPD) pattern for the title compound was analyzed and found to be crystallized in monoclinic system, space group P21/n (N° 14) with refined unit-cell parameters a = 20.795 (8) Å, b = 7.484 (2) Å, c = 10.787 (2) Å and ß = 93.96° (2). The volume of the unit cell is V = 1674.8 (6) Å3.

Keywords

indeno[2, 1-c]quinolinesantitumoral activityX-ray powder diffraction
Type
New Diffraction Data
Information
Powder Diffraction , Volume 29 , Issue 1 , March 2014 , pp. 53 - 57
Copyright
Copyright © International Centre for Diffraction Data 2013 

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References

Boultif, A. and Loüer, D. (2004). “Indexing of powder diffraction patterns of low symmetry lattices by successive dichotomy method,” J. Appl. Crystallogr. 37, 724–731.CrossRefGoogle Scholar
de Wolff, P. M. (1968). “A simplified criterion for the reliability of a powder pattern,” J. Appl. Crystallogr. 1, 108–113.CrossRefGoogle Scholar
Dong, C. (1999). “PowderX: Windows-95-based program for powder X-ray diffraction data processing,” J. Appl. Crystallogr. 32, 838–838.Google Scholar
Ewesuedo, R. B., Iyer, L., Das, S., Koenig, A., Mani, S., Vogelzang, N. J., Schilsky, R. L., Brenckman, W., and Ratain, M. J. (2001). “Phase I clinical and pharmacogenetic study of weekly TAS-103 in patients with advanced cancer,” J. Clin. Oncol. 19, 2084–2090.CrossRefGoogle ScholarPubMed
Gelderblom, H. and Sparreboom, A. (2006). “Topoisomerase inhibitors.” Drugs Affecting of Tumours, edited by Pinedo, H. M. and Smorenburg, C. H. (Birkhuser Vergal, Switzerland), pp. 83–100.Google Scholar
Ishida, K. and Asao, T. (2002). “Self-association and unique DNA binding properties of the anti-cancer agent TAS-103, a dual inhibitor of topoisomerases I and II,” Biochim. Biophys. Acta 1587, 155–163.Google Scholar
Kouznetsov, V. V., Ochoa Puentes, C., Romero Bohorquez, A. R., Zacchino, S., Sortino, M., Gupta, M., Vásquez, Y., and Bahsas, A. (2006). “A straightforward synthetic approach to antitumoral pyridinyl substituted 7H-Indeno[2,1-c]quinoline derivatives via three-component imino Diels-Alder reaction,” Lett.Org. Chem. 3, 300–304.Google Scholar
Kouznetsov, V. V., Romero Bohórquez, A. R., and Astudillo, L. (2009). “A convenient procedure for the synthesis of new α-Pyridinyl-substituted 7H-Indeno[2,1-c]quinoline derivatives based on a three-component imino Diels–Alder reaction,” Synthesis 24, 4219–4225.Google Scholar
Laugier, J. and Bochu, B. (2002). CHEKCELL. “LMGP-Suite–Suite of Programs for the interpretation of X-ray. Experiments,” ENSP/Laboratoire des Matériaux et du Génie Physique, BP 46. 38042, Saint Martin d'Hères, France. http://www.inpg.fr/LMGP and http://www.ccp14.ac.uk/tutorial/lmgp/.Google Scholar
Li, Q. -Y., Zu, Y. -G., Shi, R. -Z., and Yao, L. -P. (2006). “Review camptothecin: current perspectives,” Curr. Med. Chem. 13, 2021–2039.Google Scholar
Miguell, A. D., Hubberd, C. R., and Stalick, J. K. (1981). NBS* AIDS80: A FORTRAN Program for Crystallographic Data Evaluation. Tech. Note 1141. USA: National Bureau of Standards.CrossRefGoogle Scholar
Ohyama, T., Li, Y., Utsugi, T., Irie, S., Yamada, Y., and Sato, T. (1999). “A dual topoisomerase inhibitor, TAS-103, induces apoptosis in human cancer cells,” Jpn J. Cancer Res. 90, 691–698.Google Scholar
Pommier, Y. (2006). “Topoisomerase I inhibitors: camptothecins and beyond,” Nat. Rev. Cancer. 6, 789–802.CrossRefGoogle ScholarPubMed
Priel, E., Showalter, S. D., Roberts, M., Oroszlan, S., and Blair, D. G. (1991). “The topoisomerase I inhibitor, camptothecin, inhibits equine infectious anemia virus replication in chronically infected CF2Th cells,” J. Virol. 65, 4137–4141.CrossRefGoogle ScholarPubMed
Rachinger, W. A. (1948). “A correction for the α 1 α 2 doublet in the measurement of widths of X-ray diffraction lines,” J. Sci. Instrum. 25, 254.Google Scholar
Saviztky, A. and Golay, M. J. (1964). “Smoothing and differentiation of data by simplified least squares procedures,” Anal. Chem. 36, 1627–1639.Google Scholar
Smith, G. S. and Snyder, R. L. (1979). “ F N : a criterion for rating powder diffraction patterns and evaluating the reliability of powder-pattern indexing,” J. Appl. Crystallogr. 12, 60–65.Google Scholar
Sonneveld, E. J. and Visser, J. W. (1975). “Automatic collection of powder diffraction data from photographs,” J. Appl. Crystallogr. 8, 1–7.Google Scholar
Twelves, C. J., Gardner, C., Flavin, A., Sludden, J., Dennis, I., de Bono, J., Beale, P., Vasey, P., Hutchison, C., Macham, M. A., Rodríguez, A., Judson, I., and Bleehen, N. M. (1999). “Phase I and pharmacokinetic study of DACA (XR5000): a novel inhibitor of topoisomerase I and II,” Br. J. Cancer 80, 1786–1791.Google Scholar