411
Views
7
CrossRef citations to date
0
Altmetric
Articles

Synthesis, molecular structure exploration and in vitro cytotoxicity screening of five novel N, N′- disubstituted thiocarbamide derivatives

, , , &
Pages 507-514 | Received 26 Dec 2017, Accepted 11 Mar 2018, Published online: 18 Apr 2018

References

  • Saeed, A.; Ulrich, F.; Erben, M. F. A Review on the Chemistry, Coordination, Structure and Biological Properties of 1-(Acyl/Aroyl)-3-(Substituted) Thioureas. J. Sulfur Chem. 2014, 35, 318–355. DOI:10.1080/17415993.2013.834904.
  • Ashraf, A. Aly.; Essam, K. A.; Khaled, M. Update Survey on Aroyl Substituted Thioureas and Their Applications. J. Sulfur Chem. 2007, 28, 73–93. DOI:10.1080/17415990601124691.
  • Estevez-Hernandez, O.; Otazo-Sanchez, E. A Raman and Infrared Study of 1-Furoyl-3-Monosubstituted and 3, 3-Disubstituted Thioureas. Spectrochim. Acta Part A 2005, 62, 964–971. DOI:10.1016/j.saa.2005.04.016.
  • Otazo-Sanchez, E.; Ortiz-del-Toro, P. Aroylthioureas: New Organic Ionophores for Heavy Metal Ion Selective Electrodes. A Nuclear Magnetic Resonance Study. Spectrochim. Acta Part A 2002, 58, 2281–2290. DOI:10.1016/S1386-1425(01)00724-7.
  • Estevez-Hernandez, O.; Duque, J; Reguera, E. Structural Features of 1-Furoylthioureas 3-Monosubstituted and 3, 3-Disubstituted: Coordination to Cadmium and Analytical Applications. J. Sulfur Chem. 2011, 32, 213–222. DOI:10.1080/17415993.2011.566926.
  • Zhang, Q.; Zhao, B.; Song, Y.; Hua, Chengwen.; Gou, Xiao.; Chen, B.; Zhao, Junlong. Synthesis and Biological Activity of N-Aroyl (Aryloxyacetyl)-N-Ferrocenyl Thiourea Derivatives. Heteroatom Chem. 2015, 26, 5. DOI:10.1002/hc.21200.
  • Halim, A. N. A.; Ngaini, Z. Synthesis and Characterization of Halogenated Bis (Acylthiourea) Derivatives and Their Antibacterial Activities. Phosphorus Sulfur Silicon Relat. Elem. 2017, 192, 1012–1017. DOI:10.1080/10426507.2017.1315421.
  • Yuan, Y. F.; Wang, JiTao.; Gimeno, M. C.; Laguna, A.; Jones, P. G. Synthesis and Characterisation of Copper Complexes with N-Ferrocenoyl-N-Aryl(Alkyl) Thioureas. Inorg. Chim. Acta. 2001, 324, 309–317. DOI:10.1016/S0020-1693(01)00661-2.
  • Xian, L.; Wei, T.; Zhang, Y. M. Synthesis and Crystal Structure of Bis (N-O-Methylphenyl-N′-Ethoxycarbonylthiourea) Copper (I) Chloride. J. Coord. Chem. 2004, 57, 453–457. DOI:10.1080/00958970410001671147.
  • Duque, J.; Hernández, O. E.; Reguera, E.; Ellena, J.; Corrêa, R. S. Synthesis, Characterization, and Single Crystal X-ray Structure of the 1-Furoyl-3-Cyclohexylthiourea Cadmium Chloride Complex, Cd[C4H3OC(O)NHC(S)NHC6H11]4Cl2. J. Coord. Chem. 2009, 62, 2804–2813. DOI:10.1080/00958970902926795.
  • Li, D.; Che, D. J.; Li, Z. F.; Zhu, Y.; Zou, D. P. Versatile Coordination Patterns in the Reaction System of N-Benzoyl-N′-(2-Pyridyl) Thiourea with CuCl2. Their Reaction Conditions, Systematic Isolation and Crystal Structures. New J.Chem. 2002, 26, 1629–1633. DOI:10.1039/B206257G.
  • Singh, D. P.; Pratap, S.; Shukla, M. Solvent Induced Geometry Transformation of Trigonal Planar Cu(I) Complexes of N-((2/4-Methyoxy Carbonyl) Phenyl)-N′-(Ethoxy/Methoxy Carbonyl) Thiocarbamides to Square-Planar Cu(II) Complexes: Synthesis, Spectral, Single Crystal, DFT and in Vitro Cytotoxic Study. Inorg.Chim. Acta 2014, 423, 386–396. DOI:10.1016/j.ica.2014.08.031.
  • Singh, D. P.; Pratap, S.; Pandey, S. K.; Butcher, R. J.; Marverti, G. N-(Naphthyl)-N′-(Methoxy Carbonyl) Thiocarbamide and Its Cu(I) Complex: Synthesis, Spectroscopic, X-ray, DFT and in Vitro Cytotoxicity Study. J. Coord. Chem. 2015, 68, 261–276. DOI:10.1080/00958972.2014.979165.
  • Khanam, S.; Pandey, S. K.; Rai, S. K.; Verma, D.; Jasinski, J. P.; Pratap, S.; Tewari, A. K. Synthesis of N, N-Bis-Sulfonylated and N-Alkyl-N-Sulfonylated G1 Dendrimers Via Click Reaction: Application of Thiocarbamide Based Cu(I) Catalysts. Chem. Select. 2017, 2, 6370–6374.
  • Wang, Dan.; Wu, Su-Yun.; Li, Hai-Pu.; Yang, Y.; Roesky, H. W. Synthesis and Characterization of Copper Complexes with the N-(2,6-Diisopropylphenyl)-N′-Acylthiourea Ligands. Eur. J. Inorg. Chem. 2017, 1406–1413. DOI:10.1002/ejic.201601451.
  • Santini, C.; Pellei, M.; Gandin, V.; Porchia, M.; Tisato, F. C.; Marzano, C. Advances in Copper Complexes as Anticancer Agents. Chem. Rev. 2014, 114, 815–862. DOI:10.1021/cr400135x.
  • Eatock, M. M.; Schatzlein, A.; Kaye, S. B. Tumour Vasculature as a Target for Anticancer Therapy. Cancer Treat. Rev. 2000, 26, 191. DOI:10.1053/ctrv.1999.0158.
  • Marverti, G.; Ligabue, A.; Lombardi, P.; Ferrari, S.; Monti, M. G.; Frassineti, C.; Costi, M. P. Modulation of the Expression of Folate Cycle Enzymes and Polyamine Metabolism by Berberine in Cisplatin-Sensitive and -Resistant Human Ovarian Cancer Cells. Int. J. Oncol. 2013, 43, 1269–1280. DOI:10.3892/ijo.2013.2045.
  • Li, H. Q.; Yan, Tao.; Yang, Ying. Synthesis and Structure.Activity Relationships of N-Benzyl-N-(X-2-Hydroxybenzyl)-N′-Phenylureas and Thioureas as Antitumor Agents. Bioorg. Med. Chem. 2010, 18, 305–313. DOI:10.1016/j.bmc.2009.10.054.
  • Zhang, Y. M.; Wei, T. B.; Xian, L.; Gao, L. M. An Efficient Synthesis of Polymethylene Bis-Aroyl Thiourea Derivatives Under the Condition of Phase-Transfer Catalysis. Phosphorus Sulfur Silicon Relat. Elem. 2004, 179, 2007–2013. DOI:10.1080/10426500490473456.
  • Solomon, V. R.; Haq, W.; Smilkstein, M.; Srivastava, K.; Puri, S. K.; Katti, S. B. 4-Aminoquinoline Derived Antimalarials: Synthesis, Antiplasmodial Activity and Heme Polymerization Inhibition Studies. Eur. J. Med. Chem. 2010, 45, 4990–4996. DOI:10.1016/j.ejmech.2010.07.068.
  • Li, Q. J.; Yang, C. L. Synthesis and Crystal Structure of a Compound with Two Conformational Isomers: N-(2-Methylbenzoyl)-N′-(4-Nitrophenyl) Thiourea. J. Chem. Crystallogr. 2008, 38, 927–930. DOI:10.1007/s10870-008-9413-z.
  • Selvakumaran, N.; Pratheepkumar, A.; Ng, S. W.; Karvembu, R. Synthesis, Structural Characterization and Cytotoxicity of Nickel (II) Complexes Containing 3, 3-Dialkyl/Aryl-1-Benzoylthiourea Ligands. Inorg.Chim. Acta 2013, 404, 82–87. DOI:10.1016/j.ica.2013.04.024.
  • Maurya, M. R.; Uprety, Bhawna. Palladium (II) Complexes of OS Donor N-(Di(Butyl/Phenyl)Carbamothioyl) Benzamide and Their Antiamoebic Activity. Eur. J. Med. Chem. 2015, 98, 54–60. DOI:10.1016/j.ejmech.2015.05.006.
  • Venkatachalam, T. K.; Mao, C.; Uckun, F. M. Effect of Stereochemistry on the Anti-HIV Activity of Chiral Thiourea Compounds. Bioorg. Med. Chem. 2004, 12, 4275–4284. DOI:10.1016/j.bmc.2004.04.050.
  • Saeed, S.; Rashid, N.; Jones, P. G.; Ali, M.; Hussain, R. Synthesis, Characterization and Biological Evaluation of Some Thiourea Derivatives Bearing Benzothiazole Moiety as Potential Antimicrobial and Anticancer Agents. Eur. J. Med. Chem. 2010, 45, 1323–1331. DOI:10.1016/j.ejmech.2009.12.016.
  • Hernandez, O. E.; Duque, J.; Reguera, E. Structural Features of 1-Furoylthioureas 3-Monosubstituted and 3, 3-Disubstituted: Coordination to Cadmium and Analytical Applications. J. Sulfur Chem. 2011, 32, 213–222. DOI:10.1080/17415993.2011.566926.
  • Luckay, R. C.; Mebrahtu, F.; Esterhuysen, C.; Koch, K. R. Extraction and Transport of Gold(III) Using Some Acyl(Aroyl)Thiourea Ligands and a Crystal Structure of One of the Complexes. Inorg. Chem. Commun. 2010, 13, 468–470. DOI:10.1016/j.inoche.2010.01.010.
  • Seshadri, T.; Haupt, H. J. Thermotropic Properties of Monosubstituted Ferrocene Derivatives Bearing Bidentate N-Benzoyl-N'-Arylthiourea Ligands Novel Building Blocks for Heterometallic Liquid Crystal Systems. J. Mater. Chem. 1998, 8, 1345–1350. DOI:10.1039/a708738a.
  • Seshadri, T.; Haupt, H. J.; Florke, U.; Herald, G. Novel Cholesteric Glassy Liquid Crystals of Monosubstituted Ferrocenes: Synthesis and Selective Reflection Properties of a Dimesogen, and Crystal Atructure of a Monomesogen. Liq. Cryst. 2007, 34, 33–47. DOI:10.1080/02678290601033008.
  • Venkataramanan, V.; Srinivasan, M. R.; Bhat H. L. Vibrational Spectroscopic Study of Zinc Tris (Thiourea) Sulphate, a New Organometallic Non-Linear Optical Crystal. J. Raman Spectrosc. 1994, 25, 805–811. DOI:10.1002/jrs.1250251006.
  • Venkataramanan, V.; Bhat, H. L.; Srinivasan, M. R.; Ayyub, P.; Multan, M. S. Vibrational Spectroscopic Study of the Semiorganic Non-Linear Optical Crystal Bis (Thiourea) Cadmium Chloride. J. Raman Spectrosc. 1997, 28, 779–784. DOI:10.1002/(SICI)1097-4555(199710)28:10<779::AID-JRS147>3.0.CO;2-5.
  • Gunasekaran, N.; Ramesh, P.; Ronnuswami, M. N. G.; Karvembu, R. Monodentate Coordination of N-[Di(Phenyl/Ethyl)Carbamothioyl] Benzamide Ligands: Synthesis, Crystal Structure and Catalytic Oxidation Property of Cu(I) Complexes. Dalton Trans. 2011, 40, 12519–12526. DOI:10.1039/c1dt10628g.
  • Gunasekaran, N.; Jerome, P.; Ng, S. W.; Tiekink, E. R. T.; Karvembu, R. Tris-Chelate Complexes of Cobalt(III) with N-[Di(Alkyl/Aryl)Carbamothioyl] Benzamide Derivatives: Synthesis, Crystallography and Catalytic Activity in TBHP Oxidation of Alcohols. J. Mol. Catl. 2012, 353, 156–162. DOI:10.1016/j.molcata.2011.11.019.
  • Saeed, A.; Erben, M. F.; Bolte, M. Synthesis, Structural and Vibrational Properties of 1-(Adamantane-1-Carbonyl)-3-Halophenyl Thioureas. Spectrochim. Acta. 2013, 102, 408–413. DOI:10.1016/j.saa.2012.10.043.
  • Qiao, Lei; Zhang, Yu; Hu, Wei; Guo, J.; Cao, W.; Ding, Z.; Guo, Z.; Fan, A.; Song, J.; Huang, J. Synthesis, Structural Characterization and Quantum Chemical Calculations on 1-(Isomeric Methyl Benzoyl)-3-(4- Trifluoromethylphenyl) Thioureas. J. Mol. Struct. 2017, 1141, 309–321. DOI:10.1016/j.molstruc.2017.03.113.
  • Silverstein, R. M.; Webster, F. X.; Kiemle, D. J. Spectrometric Identification of Organic Compounds, Seventh Edition; Wiley: New York. ISBN0-471−39362-2.
  • Weiqun, Z.; Kuishenga, L.; Zhang, Y.; Lu, L. Structural and Spectral Studies of N-(4-Chloro) Benzoyl-N′-2-Tolylthiourea. J. Mol. Struct. 2003, 657, 215–223. DOI:10.1016/S0022-2860(03)00371-5.
  • Wang, G.; Cheng, M. Synthesis, Characterization, and Crystal Structure of N-P-Bromophenyl-N′-Phenylacetylthiourea. J. Chem. Crystallogr. 2009, 39, 612–614. DOI:10.1007/s10870-009-9551-y.
  • Farrugia, L. WinGX and ORTEP for Windows: an update. J. Appl. Cryst. 2012, 45, 849–854. DOI:10.1107/S0021889812029111.
  • Burnett, M. N.; Johnson, C. K. Oak ridge thermal ellipsoid plot program for crystal structure illustrations. 1996, Report ORNL-6895, Oak Ridge National Laboratory, Oak Ridge, TN.
  • Macrae, C. F.; Bruno, I. J.; Chisholm, J. A.; Edgington, P. R.; McCabe, P.; Pidcock, E.; Rodriguez-Monge, L.; Taylor, R. Mercury CSD 2.0 New Features for the Visualization and Investigation of Crystal Structures. J. Appl. Cryst. 2008, 41, 466. DOI:10.1107/S0021889807067908.
  • Korch, C.; Spillman, M. A.; Jackson, T. A.; Jacobsen, B. M.; Murphy, S. K.; Lessey, B. A.; Jordan, V. C.; Bradford, A. P. DNA Profiling Analysis of Endometrial and Ovarian Cell Lines Reveals Misidentification, Redundancy and Contamination. Gynecol. Oncol. 2012, 127, 241–248. DOI:10.1016/j.ygyno.2012.06.017.
  • Andrews, P. A.; Jones, J. A. Characterization of Binding Proteins From Ovarian Carcinoma and Kidney Tubule Cells That Are Specific for Cisplatin Modified DNA. Cancer Commun. 1991, 3, 93–102. DOI:10.3727/095535491820873524.
  • Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods. 1983, 65, 55–63. DOI:10.1016/0022-1759(83)90303-4.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.