Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

The Synthesis and Theoretical Anti-Tumor Studies of Some New Monoaza-10H-Phenothiazine and 10H-Phenoxazine Heterocycles

Efeturi A. Onoabedje1, Sunday N. Okafor2, Kovo G. Akpomie1, Uchechukwu C. Okoro1.
Affiliation: 
1 Department of Pure & Industrial Chemistry, University of Nigeria, Nsukka, Nigeria 2 Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, Nsukka, Nigeria uchechukwu.okoro@unn.edu.ng
DOI: 
https://doi.org/10.23939/chcht13.03.288
AttachmentSize
PDF icon full_text.pdf422.29 KB

Keywords:

Abstract: 
The synthesis and anticancer activity of a series of new 3-amido derivatives of 3-chloro-10H-pyrido[3,2-b][1,4]benzoxazine and 3-chloro-10H-pyrido[3,2-b][1,4]benzothiazine is presented. The synthesized structures were characterized by UV-visible, FT-IR, 1H NMR spectroscopy and elemental analytical data. The in silico physicochemical properties disclosed that neither 3-chloro-10H-pyrido[3,2-b][1,4]benzoxazine and 3-chloro-10H-pyrido[3,2-b][1,4]benzothiazine intermediates nor their carboxyamido derivatives violate Lipinski’s rule of five. In addition, molecular docking studies showed that they exhibited good interaction with cancer receptors. 1,3-di-10H-Pyrido[3,2-b][1,4]benzothiazin-3-ylurea which showed a significant interaction with all the employed receptors possessed the highest anticancer activity.
References: 

[1] Pluta K., Morak-Mlodawska B., Jelen M.: Eur. J. Med. Chem., 2011, 46, 3180. https://doi.org/10.1016/j.ejmech.2011.05.013
[2] Aaron J., Gaye Seye M., Trajkovska S. et al.: Top. Heterocycl. Chem., 2009, 16, 202. https://doi.org/10.1007/7081_2008_125
[3] Motohashi N., Sakagami H., Kamata K., Yamamoto Y.: Anticancer Res., 1991, 11, 1933.
[4] Pluta K., Jelen M., Morak-Mlodawska B. et al.: Pharmacology Rep., 2010, 62, 319. https://doi.org/10.1016/S1734-1140(10)70272-3
[5] Miyano-Kurosaki N, Ikegami K., Kurosaki K. et al.: J. Pharmacol. Sci., 2009, 110, 87. https://doi.org/10.1254/jphs.08347FP
[6] Thimmaiah K., Horton K., Seshadri R. et al.: J. Med. Chem., 1992, 35, 3358. https://doi.org/10.1021/jm00096a009
[7] Shimizu S., Suzuki M., Tomoda A. et al.: Tohoku J. Exp. Med., 2004, 203, 47.
[8] Kato S., Shirato K., Imaizumi K. et al.: Oncol. Rep., 2006, 15, 843.
[9] Azuine M., Tokuda H., Takayasu J. et al.: Pharmacol. Res., 2004, 49, 161. https://doi.org/10.1016/j.phrs.2003.07.014
[10] Onoabedje E., Ibezim A., Okafor S. et al.: PLoS ONE, 2016, 11, e0163467. https://doi.org/10.1371/journal.pone.0163467
[11] Ghorab M., Alsaid M., Al-Dosary M. et al.: Chem. Cent. J., 2016, 10, 1. https://doi.org/10.1186/s13065-016-0148-1
[12] Ullah M.: Asian Pacific J. Cancer Prev., 2008, 9, 1.
[13] Fors B., Dooleweerdt K., Zeng Q. et al.: Tetrahedron, 2009, 65, 6576. https://doi.org/10.1016/j.tet.2009.04.096
[14] Brett P., Philip K., Strieter F. et al.: Org. Lett., 2008, 10, 3505. https://doi.org/10.1021/ol801285g
[15] Yin J., Buchwald S.: Org. Lett., 2000, 2, 1101. https://doi.org/10.1021/ol005654r
[16] Buchwald S., Yin J.: Tetrahedron, 2009, 65, 6576. https://doi.org/10.1016/j.tet.2009.04.096
[17] Agbo S., Anoh V., Okoro U.: J. Applicable Chem., 2014, 3, 2526.
[18] Shima F., Ijiri Y., Muraoka S. et al.: J. Biol. Chem., 2010, 285, 22696. https://doi.org/10.1074/jbc.M110.125161
[19] Colombo R., Caldarelli M., Mennecozzi M. et al.: J. Moll. Cancer Res., 2010, 70, 10255. https://doi.org/10.1158/0008-5472.CAN-10-2101
[20] Pai E., Krengel U., Petsko G. et al.: EMBO J., 1990, 9, 2351. https://doi.org/10.1002/j.1460-2075.1990.tb07409.x
[21] Matias P., Carrondo M., Coelho R. et al. J. Med. Chem., 2002, 45, 1439. https://doi.org/10.1021/jm011072j
[22] Dong Q., Dougan D., Gong X. et al.: Bioorg. Med. Chem. Lett., 2011, 21, 1315. https://doi.org/10.1016/j.bmcl.2011.01.071
[23] Colombo R., Caldarelli M., Mennecozzi M.: Cancer Res., 2010, 70, 10255. https://doi.org/10.1158/0008-5472.CAN-10-2101
[24] Rajalingam K., Schreck R., Rapp U., Albert S.: Biochim. Biophys. Acta, 2007, 1773, 1177. https://doi.org/10.1016/j.bbamcr.2007.01.012
[25] Dassault Systèmes BIOVIA, Discovery Studio Modeling Environment, Release 2017, San Diego: Dassault Systèmes, 2016.
[26] ACD/ChemSketch (Freeware), version 15.01, Advanced Chemistry Development, Inc., Toronto, ON, Canada, www.acdlabs.com, 2015.
[27] Boyle N., Banck M., James C. et al.: J. Chemoinform., 2011, 3, 33. https://doi.org/10.1186/1758-2946-3-33
[28] Morris G., Huey R., Lindstrom W. et al.: J. Comput. Chem., 2009, 16, 2785. https://doi.org/10.1002/jcc.21256
[29] Trott O., Olson A.: J. Comput. Chem., 2010, 31, 455. https://doi.org/10.1002/jcc.21334
[30] The PyMOL Molecular Graphics System, Version 1.8 Schrödinger, LLC.
[31] Okafor C., Castle R., Wise Jr. D.: J. Heterocyclic Chem., 1983, 20, 1047. https://doi.org/10.1002/jhet.5570200441
[32] Okafor C., Uche I., Akpanisi L.: J. Heterocyclic Chem., 1981, 18, 1589. https://doi.org/10.1002/jhet.5570180820
[33] Veber D., Stephen R., Hung-Yuan C. et al.: J. Med. Chem., 2002, 45, 2615. https://doi.org/10.1021/jm020017n