535
Views
12
CrossRef citations to date
0
Altmetric
Review

A survey of crystal structures and biological activities of platinum group metal complexes containing N-acylthiourea ligands

&
Pages 779-804 | Received 18 Oct 2019, Accepted 27 Apr 2020, Published online: 19 May 2020

References

  • Larik, F. A.; Saeed, A.; Faisal, M.; Ali Channar, P.; Azam, S. S.; Ismail, H.; Dilshad, E.; Mirza, B. Synthesis, Molecular Docking and Comparative Efficacy of Various Alkyl/Aryl Thioureas as Antibacterial, Antifungal and α-Amylase Inhibitors. Comput. Biol. Chem. 2018, 77, 193–198. DOI: 10.1016/j.compbiolchem.2018.10.007.
  • Xie, J.; Cheng, Z.; Yang, W.; Liu, H.; Zhou, W.; Li, M.; Xu, Y. Crystal Structures and Antimicrobial and Cytotoxic Activities of Zinc(II), Nickel(II) and Copper(II) Complexes of N‐(Piperidylthiocarbonyl)Benzamide. Appl. Organometal. Chem. 2015, 29, 157–164. DOI: 10.1002/aoc.3262.
  • Mishra, P.; Kumar, A.; Mamidi, P.; Kumar, S.; Basantray, I.; Saswat, T.; Das, I.; Nayak, T. K.; Chattopadhyay, S.; Subudhi, B. B. Inhibition of Chikungunya Virus Replication by 1-[(2-Methylbenzimidazol-1-yl) Methyl]-2-Oxo-Indolin-3-Ylidene] Amino] Thiourea(MBZM-N-IBT). Sci. Rep 2016, 6, 20122. DOI: 10.1038/srep20122.
  • Nishida, C. R.; Ortiz de Montellano, P. R. de Montellano, P. R. O. Bioactivation of Antituberculosis Thioamide and Thiourea Prodrugs by Bacterial and Mammalian Flavin Monooxygenases. Chem. Biol. Interact 2011, 192, 21–25. DOI: 10.1016/j.cbi.2010.09.015.
  • Ruswanto, A. M.; Miftah, D. H.; Siswandono, T. Synthesis and in Vitro Cytotoxicity of 1-Benzoyl-3-Methylthiourea Derivatives. Procedia Chem. 2015, 17, 157–161. DOI: 10.1016/j.proche.2015.12.105.
  • Ullah, I.; Shah, A.; Badshah, A.; Shah, A.; Shah, N. A.; Tabor, R. Characterizations and Multifunctional Activities of New Thiourea-Based Non-Ionic Surfactants. Colloids Surf. A 2015, 464, 104–110. DOI: 10.1016/j.colsurfa.2014.10.002.
  • Fakhar, I.; Hussien, N. J.; Sapari, S.; Bloh, A. H.; Mohd Yusoff, S. F.; Hasbullah, S. A.; Yamin, B. M.; Mutalib, S. A.; Shihab, M. S.; Yousif, E. Synthesis, X-Ray Diffraction, Theoretical and anti-Bacterial Studies of Bis-Thiourea Secondary Amine. J. Mol. Struct. 2018, 1159, 96–102. DOI: 10.1016/j.molstruc.2018.01.032.
  • Tuncel, S. T.; Gunal, S. E.; Ekizoglu, M.; Kelekci, N. G.; Erdem, S. S.; Bulak, E.; Frey, W.; Dogan, I. Thioureas and Their Cyclized Derivatives: Synthesis, Conformational Analysis and Antimicrobial Evaluation. J. Mol. Struct. 2019, 1179, 40–56. DOI: 10.1016/j.molstruc.2018.10.055.
  • Saeed, A.; Bosch, A.; Bettiol, M.; González, D. L. N.; Erben, M. F.; Lamberti, Y. Novel Guanidine Compound against Multidrug-Resistant Cystic Fibrosis-Associated Bacterial Species. Molecules 2018, 23, 1158–1158. DOI: 10.3390/molecules23051158.
  • Khairul, W. M.; Daud, A. I.; Ismail N. Understanding the properties of chitosan aryl substituted thioureas in their role and potential as antibacterial agents. AIP Conf. Proc. 2018, 1933, 20002. DOI: 10.1063/1.5023936.
  • Mohamed, N. A.; Abd El-Ghany, N. A.; Fahmy, M. M. Novel Antimicrobial Superporous Cross-Linked Chitosan/Pyromellitimide Benzoyl Thiourea Hydrogels. Int. J. Biol. Macromol. 2016, 82, 589–598. DOI: 10.1016/j.ijbiomac.2015.09.023.
  • Mohamed, N. A.; Al-Mehbad, N. Y. Novel Terephthaloyl Thiourea Cross-Linked Chitosan Hydrogels as Antibacterial and Antifungal Agents. Int. J. Biol. Macromol. 2013, 57, 111–117. DOI: 10.1016/j.ijbiomac.2013.03.007.
  • Mohamed, N. A.; Al-Harby, N. F.; Almarshed, M. S. Synthesis and Characterization of Novel Trimellitic Anhydride Isothiocyanate-Cross Linked Chitosan Hydrogels Modified with Multiwalled Carbon Nanotubes for Enhancement of Antimicrobial Activity. Int. J. Biol. Macromol. 2019, 132, 416–428. DOI: 10.1016/j.ijbiomac.2019.03.195.
  • Rosenberg, B.; Van Camp, L.; Trosko, J. E.; Mansour, V. H. Platinum Compounds: A New Class of Potent Antitumour Agents. Nature 1969, 222, 385–386. DOI: 10.1038/222385a0.
  • Muggia, F. Platinum Compounds 30 Years after the Introduction of Cisplatin: Implications for the Treatment of Ovarian Cancer. Gynecol. Oncol. 2009, 112, 275–281. DOI: 10.1016/j.ygyno.2008.09.034.
  • Clarke, M. J. Ruthenium Metallopharmaceuticals. Coord. Chem. Rev. 2003, 236, 209–233. DOI: 10.1016/S0010-8545(02)00312-0.
  • Lazarevic, T.; Rilak, A.; Bugarcic, Z. D. Platinum, Palladium, Gold and Ruthenium Complexes as Anticancer Agents: Current Clinical Uses, Cytotoxicity Studies and Future Perspectives. Eur. J. Med. Chem. 2017, 142, 8–31. DOI: 10.1016/j.ejmech.2017.04.007.
  • Pieper, T.; Borsky, K.; Keppler, B. K. Non-Platinum Antitumor Compounds. Top. Biol. Inorg. Chem. 1999, 1, 171–199. DOI: 10.1007/978-3-662-03815-4_7.
  • El-Morsy, F. A.; Jean-Claude, B. J.; Butler, I. S.; El-Sayed, S. A.; Mostafa, S. I. Synthesis, Characterization and Anticancer Activity of New Zinc(II),Molybdate(II), Palladium(II), Silver(I), Rhodium(III), Ruthenium(II) and Platinum(II) Complexes of 5,6-Diamino-4-Hydroxy- 2-Mercaptopyrimidine. Inorg. Chim. Acta 2014, 423, 144–155. DOI: 10.1016/j.ica.2014.07.031.
  • Moro, A. C.; Mauro, A. E.; Netto, A. V. G.; Ananias, S. R.; Quilles, M. B.; Carlos, I. Z.; Pavan, F. R.; Leite, C. Q. F.; Hörner, M. Antitumor and Antimycobacterial Activities of Cyclopalladated Complexes: X-Ray Structure of [Pd(C2,N-Dmba)(Br)(tu)] (Dmba = N,N-Dimethylbenzylamine, tu = Thiourea). Eur. J. Med. Chem. 2009, 44, 4611–4615. DOI: 10.1016/j.ejmech.2009.06.032.
  • Correa, R. S.; de Oliveira, K. M.; Delolo, F. G.; Alvarez, A.; Mocelo, R.; Plutin, A. M.; Cominetti, M. R.; Castellano, E. E.; Batista, A. A. Ru(II)-Based Complexes with N-(Acyl)-N′,N′-(Disubstituted)Thiourea Ligands: Synthesis, Characterization, BSA- and DNA-Binding Studies of New Cytotoxic Agents against Lung and Prostate Tumour Cells. J. Inorg. Biochem. 2015, 150, 63–71. DOI: 10.1016/j.jinorgbio.2015.04.008.
  • Beyer, L.; Hoyer, E.; Liebscher, J.; Hartmann, H. Komplexbildung Mit N-Acyl-Thioharnstoffen. Z. Chem. 2010, 21, 81–91. DOI: 10.1002/zfch.19810210302.
  • Koch, K. R. New Chemistry with Old Ligands: N-Alkyl- and N,N-dialkyl-N′-Acyl(Aroyl)Thioureas in co-Ordination, Analytical and Process Chemistry of the Platinum Group Metals. Coord. Chem. Rev. 2001, 216, 473–488. DOI: 10.1016/S0010-8545(01)00337-X.
  • Aly, A. A.; Ahmed, E. K.; El-Mokadem, K. M.; Hegazy, A. F. Update Survey on Aroyl Substituted Thioureas and Their Applications. J. Sulfur Chem. 2007, 28, 73–93. DOI: 10.1080/17415990601124691.
  • Saeed, A.; Flörke, U.; 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.
  • Saeed, A.; Qamar, R.; Fattah, T. A.; Flörke, U.; Erben, M. F. Recent Developments in Chemistry, Coordination, Structure and Biological Aspects of 1-(Acyl/Aroyl)-3-(Substituted) Thioureas. Res. Chem. Intermed. 2017, 43, 3053–3093. DOI: 10.1007/s11164-016-2811-5.
  • Saeed, A.; Mustafa, M. N.; Zain-Ul-Abideen, M.; Shabir, G.; Erben, M. F.; Flörke, U. Current Developments in Chemistry, Coordination, Structure and Biological Aspects of 1-(Acyl/Aroyl)-3-(Substituted) Thioureas: advances Continue. J. Sulfur Chem. 2019, 40, 312–350. DOI: 10.1080/17415993.2018.1551488.
  • Mohapatra, R. K.; Das, P. K.; Pradhan, M. K.; El-Ajaily, M. M.; Das, D.; Salem, H. F.; Mahanta, U.; Badhei, G.; Parhi, P. K.; Maihub, A. A.; Kudrat-E-Zahan, M. Recent Advances in Urea and Thiourea-Based Metal Complexes: Biological, Sensor, Optical, and Corrosion Inhibition Studies. Comment Inorg. Chem. 2019, 39, 127–187. DOI: 10.1080/02603594.2019.1594204.
  • Douglass, I. B.; Dains, F. B. Some Derivatives of Benzoyl and Furoyl Isothiocyanates and Their Use in Synthesizing Heterocyclic Compounds. J. Am. Chem. Soc. 1934, 56, 719–721. DOI: 10.1021/ja01318a057.
  • Ghazal, K.; Shoaib, S.; Khan, M.; Khan, S.; Rauf, M. K.; Khan, N.; Badshah, A.; Tahir, M. N.; Ali, I.; Rehman, A. Synthesis, Characterization, X-Ray Diffraction Study, in-Vitro Cytotoxicity, Antibacterial and Antifungal Activities of Nickel(II) and Copper(II) Complexes with Acyl Thiourea Ligand. J. Mol. Struct. 2019, 1177, 124–130. DOI: 10.1016/j.molstruc.2018.09.028.
  • Rauf, M. K.; Talib, A.; Badshah, A.; Zaib, S.; Shoaib, K.; Shahid, M.; Florke, U.; Ud-Din, I.; Iqbal, J. Solution-Phase Microwave Assisted Parallel Synthesis of N,N′-Disubstituted Thioureas Derived from Benzoic Acid: Biological Evaluation and Molecular Docking Studies. Eur. J. Med. Chem. 2013, 70, 487–496. DOI: 10.1016/j.ejmech.2013.10.012.
  • de Oliveira, C. G. M.; Faria, V. W.; de Andrade, G. F.; D’Elia, E.; Cabral, M. F.; Cotrim, B. A.; Resende, G. O.; de Souza, F. C. Synthesis of Thiourea Derivatives and Its Evaluation as Corrosion Ihibitor for Carbon Steel. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 1366–1377. DOI: 10.1080/10426507.2015.1035719.
  • Rauf, M. K.; Zaib, S.; Talib, A.; Ebihara, M.; Badshah, A.; Bolte, M.; Iqbal, J. Solution-Phase Microwave Assisted Parallel Synthesis, Biological Evaluation and in Silico Docking Studies of N,N′-Disubstituted Thioureas Derived from 3-Chlorobenzoic Acid. Bioorg. Med. Chem. 2016, 24, 4452–4463. DOI: 10.1016/j.bmc.2016.07.042.
  • Yaseen, S.; Rauf, M. K.; Zaib, S.; Badshah, A.; Tahir, M. N.; Ali, M. I.; Ud-Din, I.; Shahid, M.; Iqbal, J. Synthesis, Characterization and Urease Inhibition, in Vitro Anticancer and Antileishmanial Studies of Co(III) Complexes with N,N,N′-Trisubstituted Acylthioureas. Inorg. Chim. Acta 2016, 443, 69–77. DOI: 10.1016/j.ica.2015.12.027.
  • Khan, S. I.; Khan, I. A.; Badshah, A.; Malik, F. P.; Tabassum, S.; Ullah, I.; Zargarian, D.; Rauf, M. K. Mononuclear Copper(I) complexes with Triphenylphosphine and N,N′-Disubstituted Thioureas: Synthesis, Characterization, and Biological Evaluation. J. Coord. Chem. 2018, 71, 4086–4108. DOI: 10.1080/00958972.2018.1538504.
  • Tavakol, H.; Mahmoudi, A.; Ranjbari, M. A. Synthesis of di- and Tri-Substituted Thiourea Derivatives in Water Using Choline Chloride–Urea Catalyst. J. Sulfur Chem. 2019, 40, 113–123. DOI: 10.1080/17415993.2018.1533014.
  • Dawood, K. M. Bis-Thiourea Derivatives and Their Utility in Synthesis of Mono-Heterocyclic, Bis-Heterocyclic, and Fused Heterocyclic Systems. J. Heterocyclic Chem. 2019, 56, 1701–1721. DOI: 10.1002/jhet.3540.
  • Saeed, A.; Shah, M. S.; Larik, F. A.; Khan, S. U.; Channar, P. A.; Flörke, U.; Iqbal, J. Synthesis, Computational Studies and Biological Evaluation of New 1-Acetyl-3-Aryl Thiourea Derivatives as Potent Cholinesterase Inhibitors. Med. Chem. Res. 2017, 26, 1635–1646. DOI: 10.1007/s00044-017-1829-6.
  • Kulabaş, N.; Özakpinar, Ö. B.; Özsavci, D.; Leyssen, P.; Neyts, J.; Küçükgüzel, İ. Synthesis, Characterization and Biological Evaluation of Thioureas, Acylthioureas and 4-Thiazolidinones as Anticancer and Antiviral Agents. Marmara P. J. 2017, 21, 371–384. DOI: 10.12991/marupj.300913.
  • Mumtaz, A.; Arshad, J.; Saeed, A.; Nawaz, M. A.; Iqbal, J. Synthesis, Characterization and Urease Inhibition Studies of Transition Metal Complexes of Thioureas Bearing Ibuprofen Moiety. J. Chil. Chem. Soc. 2018, 63, 3934–3940. DOI: 10.4067/s0717-97072018000203934.
  • Yeșilkaynak, T.; Muslu, H.; Özpınar, C.; Emen, F. M.; Demirdöğen, R. E.; Külcü, N. Novel Thiourea Derivative and Its Complexes: Synthesis, Characterization, DFT Computations, Thermal and Electrochemical Behavior, Antioxidant and Antitumor Activities. J. Mol. Struct. 2017, 1142, 185–193. DOI: 10.1016/j.molstruc.2017.04.049 0022-2860.
  • Gumus, I.; Solmaz, U.; Binzet, G.; Keskin, E.; Arslan, B.; Arslan, H. Hirshfeld Surface Analyses and Crystal Structures of Supramolecular Self-Assembly Thiourea Derivatives Directed by Non-Covalent Interactions. J. Mol. Struct. 2018, 1157, 78–88. DOI: 10.1016/j.molstruc.2017.12.017.
  • Pandey, S. K.; Pratap, S.; Tiwari, M. K.; Marverti, G.; Jasinski, J. P. Experimental and Theoretical Exploration of Molecular Structure and Anticancer Properties of Two N, N′–Disubstituted Thiocarbamide Derivatives. J. Mol. Struct. 2019, 1175, 963–970. DOI: 10.1016/j.molstruc.2018.08.040.
  • Qiao, L.; Huang, J.; Hu, W.; Zhang, Y.; Guo, J.; Cao, W.; Miao, K.; Qin, B.; Song, J. Synthesis, Characterization, and in Vitro Evaluation and in Silico Molecular Docking of Thiourea Derivatives Incorporating 4-(Trifluoromethyl)Phenyl Moiety. J. Mol. Struct. 2017, 1139, 149–159. DOI: 10.1016/j.molstruc.2017.03.012.
  • Khairul, W. M.; Daud, A. I.; Hanifaah, N. A. M.; Arshad, S.; Razak, I. A.; Zuki, H. M.; Erben, M. F. Structural Study of a Novel Acetylide-Thiourea Derivative and Its Evaluation as a Detector of Benzene. J. Mol. Struct. 2017, 1139, 353–361. DOI: 10.1016/j.molstruc.2017.03.065.
  • Khan, M. R.; Zaib, S.; Rauf, M. K.; Ebihara, M.; Badshah, A.; Zahid, M.; Nadeem, M. A.; Iqbal, J. Solution-Phase Microwave Assisted Parallel Synthesis, Biological Evaluation and in Silico Docking Studies of 2-Chlorobenzoyl Thioureas Derivatives. J. Mol. Struct. 2018, 1164, 354–362. DOI: 10.1016/j.molstruc.2018.03.056.
  • Cairo, R. R.; Stevens, A. M. P.; de Oliveira, T. D.; Batista, A. A.; Castellano, E. E.; Duque, J.; Soria, D. B.; Fantoni, A. C.; Corrêa, R. S.; Erbene M. F. Understanding the Conformational Changes and Molecular Structure of Furoyl Thioureas Upon Substitution. Spectrochim. Acta A. 2017, 176, 8–17. DOI: 10.1016/j.saa.2016.12.038.
  • Zhang, Y.; Zhang, X.; Qiao, L.; Ding, Z.; Hang, X.; Qin, B.; Song, J.; Huang, J. Synthesis, Structures, Drug-Likeness, in Vitro Evaluation and in Silico Docking on Novel N-benzoyl-N′-Phenyl Thiourea Derivatives. J. Mol. Struct. 2019, 1176, 335–345. DOI: 10.1016/j.molstruc.2018.08.069.
  • Kalaiyarasi, A.; Haribabu, J.; Gayathri, D.; Gomathi, K.; Bhuvanesh, N. S. P.; Karvembu, R.; Biju, V. M. Chemosensing, Molecular Docking and Antioxidant Studies of 8-Aminoquinoline Appended Acylthiourea Derivatives. J. Mol. Struct. 2019, 1185, 450–460. DOI: 10.1016/j.molstruc.2019.02.098.
  • Larik, F. A.; Shah, M. S.; Saeed, A.; Shah, H. S.; Channar, P. A.; Bolte, M.; Iqbal, J. New Cholinesterase Inhibitors for Alzheimer’s disease: Structure Activity Relationship, Kinetics and Molecular Docking Studies of 1–Butanoyl–3–arylthiourea Derivatives. Int. J. Biol. Macromol. 2018, 116, 144–150. DOI: 10.1016/j.ijbiomac.2018.05.001.
  • Xiao, S.; Wei, L.; Hong, Z.; Rao, L.; Ren, Y.; Wan, J.; Feng, L. Design, Synthesis and Algicides Activities of Thiourea Derivatives as the Novel Scaffold Aldolase Inhibitors. Bioorg. Med. Chem. 2019, 27, 805–812. DOI: 10.1016/j.bmc.2019.01.023.
  • Kanwal, B. B.; Khana, K. M.; Lodhi, A.; Salar, U.; Begum, F.; Ali, M.; Taha, M.; Perveen, S. Synthesis, in Vitro Urease Inhibitory Activity, and Molecular Docking Studies of Thiourea and Urea Derivatives. Bioorg. Chem. 2018, 80, 129–144. DOI: 10.1016/j.bioorg.2018.06.007.
  • Díaz, M.; de Lucio, H.; Moreno, E.; Espuelas, S.; Aydillo, C.; Ruiz, A. J.; Toro, M. A.; Gutiérrez, K. J.; Merino, V. M.; Cornejo, A.; et al. Synthesis and Leishmanicidal Activity of Novel Urea, Thiourea, and Selenourea Derivatives of Diselenides. Antimicrob. Agents Chemother. 2019, 63, 2200–2218. DOI: 10.1128/AAC.02200-18.
  • Antypenko, L.; Meyer, F.; Kholodniak, O.; Sadykova, Z.; Jirásková, T.; Troianova, A.; Buhaiova, V.; Cao, S.; Kovalenko, S.; Garbe, L. A.; Steffens, K. G. Novel Acyl Thiourea Derivatives: Synthesis, Antifungal Activity, Gene Toxicity, Drug-like and Molecular Docking Screening. Arch. Pharm. Chem. Life. Sci. 2019, 352, 1800275–1800. DOI: 10.1002/ardp.201800275.
  • Nordin, N. A.; Lawai, V.; Ngaini, Z.; Nadiah, A.; Halim, A.; Hwang, S. S.; Linton, R. E.; Lee, B. K.; Neilsen, P. M. In Vitro Cytotoxicity Evaluation of Thiourea Derivatives Bearing Salix sp. constituent against HK-1 Cell Lines. Nat. Product Res. 2018, 1, 10. DOI: 10.1080/14786419.2018.1517120.
  • Qiao, L.; Zhang, Y.; Hu, W.; Guo, J.; Cao, W.; Ding, Z.; Guo, Z.; Fan, A.; Song, J.; Huang, J. Synthesis, Structural Characterization and Quantum Chemical Calculations on 1-(Isomeric Methylbenzoyl)-3-(4-Trifluoromethylphenyl) Thioureas. J. Mol. Struct. 2017, 1141, 309–321. DOI: 10.1016/j.molstruc.2017.03.113.
  • Zhang, Y.; Huang, J.; Qiao, L.; Zhang, X.; Cao, W.; Ding, Z.; Hang, X.; Qin, B.; Song, J. Investigations Based on Non-Covalent Interactions in 1-(4-Chloromethylbenzoyl)-3-(4,6-di-Substituted Pyrimidine-2-yl) Thioureas: Synthesis, Characterizations and Quantum Chemical Calculations. J. Mol. Struct. 2018, 1169, 85–95. DOI: 10.1016/j.molstruc.2018.05.059.
  • Pandey, S. K.; Pratap, S.; Rai, S. K.; Marverti, G.; Kaur, M.; Jasinski, J. P. Synthesis, Characterisation, Hirshfeld Surface and in Vitro Cytotoxicity Evaluation of New N-aryl-N’-Alkoxycarbonyl Thiocarbamide Derivatives. J. Mol. Struct. 2020, 1202, 127269–127. DOI: 10.1016/j.molstruc.2019.127269.
  • Saeed, A.; Ashraf, Z.; Erben, M. F.; Simpson, J. Vibrational Spectra and Molecular Structure of Isomeric 1-(Adamantan-1-Ylcarbonyl)-3-(Dichlorophenyl)Thioureas. J. Mol. Struct. 2017, 1129, 283–291. DOI: 10.1016/j.molstruc.2016.09.039.
  • Saeed, A.; Ashraf, S.; White, J. M.; Soria, D. B.; Franca, C. A.; Erben, M. F. Synthesis, X-Ray Crystal Structure, Thermal Behavior and Spectroscopic Analysis of 1-(1-Naphthoyl)-3-(Halo-Phenyl)-Thioureas Complemented with Quantum Chemical Calculations. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2015, 150, 409–418. DOI: 10.1016/j.saa.2015.05.068.
  • Lestard, M. E. D.; Gil, D. M.; Estevez-Hernandez, O.; Erben, M. F.; Duque, J. Structural, Vibrational and Electronic Characterization of 1-Benzyl-3-Furoyl-1-Phenylthiourea: An Experimental and Theoretical Study. New J. Chem. 2015, 39, 7459–7471. DOI: 10.1039/C5NJ01210D.
  • Saeed, A.; Khurshid, A.; Bolte, M.; Fantoni, A. C.; Erben, M. F. Intra- and Intermolecular Hydrogen Bonding and Conformation in 1-Acyl Thioureas: An Experimental and Theoretical Approach on 1-(2-Chlorobenzoyl)Thiourea. Spectrochim. Acta A 2015, 143, 59–66. DOI: 10.1016/j.saa.2015.02.042.
  • Saeed, A.; Khurshid, A.; Jasinski, J. P.; Pozzi, C. G.; Fantoni, A. C.; Erben, M. F. Competing Intramolecular N-H···O = C Hydrogen Bonds and Extended Intermolecular Network in 1-(4-Chlorobenzoyl)-3-(2-Methyl-4-Oxopentan-2-yl) Thiourea Analyzed by Experimental and Theoretical Methods. Chem. Phys. 2014, 431, 39–46. DOI: 10.1016/j.chemphys.2014.01.009.
  • Abosadiya, H. M.; Anouar, E. H.; Yamin, B. M. Synthesis, X-Ray, Spectroscopic Characterization (FT-IR, NMR, UV-Vis) and Quantum Chemical Calculations of Some Substituted Benzoylthiourea Derivatives. J. Mol. Struct. 2019, 1194, 48–56. DOI: 10.1016/j.molstruc.2019.05.060.
  • Pandey, S. K.; Pratap, S.; Rai, S. K.; Marverti, G.; Kaur, M.; Jasinski, J. P. Synthesis, Characterization, Hirshfeld Surface, Cytotoxicity, DNA Damage and Cell Cycle Arrest Studies of N, N-diphenyl-N’-(Biphenyl-4-Carbonyl/4-Chlorobenzoyl) Thiocarbamides. J. Mol. Struct. 2019, 1186, 333–344. DOI: 10.1016/j.molstruc.2019.03.057.
  • Pandey, S. K.; Pratap, S.; Marverti, G.; Kaur, M.; Jasinski, J. P. Synthesis, Spectroscopic, Crystal Structure and in Vitro Cytotoxicity Studies of N-thiophenoyl-N’-Substituted Phenyl Thiocarbamide Derivatives. J. Mol. Struct. 2019, 1180, 447–454. DOI: 10.1016/j.molstruc.2018.12.011.
  • Mustafa, M. N.; Saeed, A.; Channar, P. A.; Larik, F. A.; Zain-Ul Abideen, M.; Shabir, G.; Abbas, Q.; Hassan, M.; Raza, H.; Seo, S.-Y. Synthesis, Molecular Docking and Kinetic Studies of Novel Quinolinyl Based Acyl Thioureas as Mushroom Tyrosinase Inhibitors and Free Radical Scavengers. Bioorg. Chem. 2019, 90, 103063–103. DOI: 10.1016/j.bioorg.2019.103063.
  • Hussain, M.; Arshad, N.; Ujan, R.; Saeed, A.; Channar, P. A.; Perveen, F.; Larik, F. A.; Farooqi, S. I.; Hussain, Z.; Hokelek, T.; et al. Synthesis, Structure Elucidation and Surface Analysis of a New Single Crystal N-((2-(Benzo [4,5]Imidazo [1,2-c]Quinazolin-6-yl)Phenyl) Carbamothioyl)Heptanamide: Theoretical and Experimental DNA Binding Studies. J. Mol. Struct. 2020, 1205, 127496–127. DOI: 10.1016/j.molstruc.2019.127496.
  • Saeed, A.; Bolte, M.; Erben, M. F.; Pérez, H. Intermolecular Interactions in Crystalline 1-(Adamantane-1-Carbonyl)-3-Substituted Thioureas with Hirshfeld Surface Analysis. Cryst. Eng. Comm. 2015, 17, 7551–7563. DOI: 10.1039/C5CE01373A.
  • Saeed, A.; Ashraf, S.; Florke, U.; Yuliana, Z.; Espinoza, D.; Erben, M. F.; Perez, H. Supramolecular Self-Assembly of a Coumarine-Based Acylthiourea Synthon Directed by π-Stacking Interactions: Crystal Structure and Hirshfeld Surface Analysis. J. Mol. Struct. 2016, 1111, 76–83. DOI: 10.1016/j.molstruc.2016.01.074.
  • Gumus, I.; Solmaz, U.; Binzet, G.; Keskin, E.; Arslan, B.; Arslan, H. Supramolecular Self-Assembly of New Thiourea Derivatives Directed by Intermolecular Hydrogen Bonds and Weak Interactions: crystal Structures and Hirshfeld Surface Analysis. Res. Chem. Intermed. 2019, 45, 169–198. DOI: 10.1007/s11164-018-3596-5.
  • Nkabyo, H. A.; Koch, K. R. New Trans-[Pd(L-κS,O)2] Complexes from N,N-dialkyl-N′-Aroylthioureas Prepared by Photo-Induced Isomerization of Their Cis-[Pd(L-κS,O)2] Counterparts and Their Thermal Trans-Cis Isomerization. Inorg. Chim. Acta 2018, 483, 440–447. DOI: 10.1016/j.ica.2018.08.028.
  • Nkabyo, H. A.; Koch, K. R. Configurational E/Z and photo-induced cis-trans isomerism in the Pd(II) complex of asymmetrical N,N-methyl-ethyl-N’-benzoylthiourea. J. Mol. Struct. 2019, 1190, 47–53. DOI: 10.1016/j.molstruc.2019.04.038.
  • Nkabyo, H. A.; Procacci, B.; Duckett, S. B.; Koch, K. R. Reversible Photo-Isomerization of Cis-[Pd(L-κS,O)2] (HL = N,N-diethyl-N’-1-Naphthoylthiourea) to Trans-[Pd(L-κS,O)2] and the Unprecedented Formation of Trans-[Pd(L-κS,N)2] in Solution. Dalton Trans. 2019, 48, 17241–17251. DOI: 10.1039/C9DT03672E.
  • Gunasekaran, N. Palladium(II) Complexes with 2,4-dichloro-N-[di(Alkyl/Aryl) Carbamothioyl] Benzamide Derivatives and Triphenylphosphine as Effective Catalysts for Oxidation of Alcohols in Ionic Liquid. Inorg. Chem. Commun. 2018, 89, 55–59. DOI: 10.1016/j.inoche.2018.01.008.
  • Khan M. R.; ZaibS.; Khan, A.; Badshah, A.; Rauf, M. K.; Ud-Din, I.; Tahir, M. N.; Shahid, M.; Iqbal, J. Pd(II)-Based Heteroleptic Complexes with N-acyl-N′,N′-(Disubstituted) Thioureas and Phosphine Ligands: Synthesis, Characterization and Cytotoxic Studies against Lung Squamous, Breast Adenocarcinoma and Leishmania tropica. Inorg. Chim. Acta 2018, 479, 189–196. DOI: 10.1016/j.ica.2018.04.060.
  • Plutín, A. M.; Alvarez, A.; Mocelo, R.; Ramos, R.; Castellano, E. E.; da Silva, M. M.; Villarreal, W.; Pavan, F. R.; Meira, C. S.; Filho, J. S. R.; et al. Palladium(II)/N,N-disubstituted-N’-Acylthioureas Complexes as anti-Mycobacterium tuberculosis and anti-Trypanosoma cruzi Agents. Polyhedron 2017, 132, 70–77. DOI: 10.1016/j.poly.2017.05.003.
  • Rohini, G.; Ramaiah, K.; Aneesrahman, K. N.; Aryasenan, M. C.; Bhuvanesh N. S. P., Reddy, K. L.; Sreekanth, A. Biological evaluation, DNA/protein-binding aptitude of novel dibenzosuberene appended palladium (II)-thiourea complexes. Appl. Organometal. Chem. 2018, 32, 4567. DOI: 10.1002/aoc.4567.
  • Jeyalakshmi, K.; Haribabu, J.; Balachandran, C.; Bhuvanesh, N. S. P.; Emi, N.; Karvembu, R. Synthesis of Ru(II)–Benzene Complexes Containing Aroylthiourea Ligands, and Their Binding with Biomolecules and in Vitro Cytotoxicity through Apoptosis. New J. Chem. 2017, 41, 2672–2686. DOI: 10.1039/C6NJ03099H.
  • Vegas, L. C.; Dulcey, L. L.; Plutín, A. M.; Castellano, E. E.; Cominetti, M. R.; Batista, A. A. Half Sandwich Ru(II)-Acylthiourea Complexes: DNA/HSA-Binding, anti-Migration and Cell Death in a Human Breast Tumor Cell Line. Dalton Trans. 2017, 46, 12865–12875. DOI: 10.1039/C7DT01801K.
  • Solmaz, U.; Gumus, I.; Binzet, G.; Celik, O.; Balci, G. K.; Dogen, A.; Arslan, H. Synthesis, Characterization, Crystal Structure, and Antimicrobial Studies of Novel Thiourea Derivative Ligands and Their Platinum Complexes. J. Coord. Chem. 2018, 71, 200–218. DOI: 10.1080/00958972.2018.1427233.
  • Pérez, H.; Ramos, R.; Plutín, A. M.; Mocelo, R.; Erben, M. F.; Castellano, E. E.; Batista, A. A. A Mixed Ligand Platinum(II) Complex: Spectral Analysis, Crystal Structure, Steric Demand of the Ligand, and Bioactivity of Cis-[Pt(PPh3)2(L1-O,S)]PF6 (L1-O,S = N,N-Morpholine-N′-Benzoylthiourea). Eur.J.Inorg. Chem. 2019, 2019, 2583–2590. DOI: 10.1002/ejic.201900042.
  • Correa, R. S.; Oliveira, K. M.; Perez, H.; Plutin, A. M.; Ramos, R.; Mocelo, R.; Castellano, E. E.; Batista, A. A. cis-bis(N-benzoyl-N’,N’-dibenzylthioureido) Platinum(II): Synthesis, Molecular Structure and its Interaction with Human and Bovine Serum Albumin. Arab. J. Chem. 2019, 12, 3454–3462. DOI: 10.1016/j.arabjc.2015.10.006.
  • Mawnai, I. L.; Adhikari, S.; Kaminsky, W.; Kollipara, M. R. Synthesis of Strained Complexes of Arene d6 Metals with Benzoylthiourea and Their Spectral Studies. J. Organomet. Chem. 2018, 869, 26–36. DOI: 10.1016/j.jorganchem.2018.05.023.
  • Lapasam, A.; Hussain, O.; Phillips, R. M.; Kaminsky, W.; Kollipara, M. R. Synthesis, Characterization and Chemosensitivity Studies of Half-Sandwich Ruthenium, Rhodium and Iridium Complexes Containing к1(S) and к2(N,S) Aroylthiourea Ligands. J. Organomet. Chem. 2019, 880, 272–280. DOI: 10.1016/j.jorganchem.2018.11.020.
  • Kalidasan, M.; Nagarajaprakash, R.; Kollipara, M. R. Synthesis and Molecular Studies of Half-Sandwich Arene Ruthenium and Cp*Rh/Cp*Ir Complexes Containing (3-Picolyl)Thiourea Derivatives as N,S-Bidentate Donor Ligands. Transition Met. Chem. 2015, 40, 531–539. DOI: 10.1007/s11243-015-9946-x.
  • Kalidasan, M.; Nagarajaprakash, R.; Forbes, S.; Mozharivskyj, Y.; Kollipara, M. R. Synthesis, Spectroscopic and Molecular Studies of Half‐Sandwich η6‐Arene Ruthenium, Cp* Rhodium and Cp* Iridium Metal Complexes with Bidentate Ligands. Z. Anorg. Allg. Chem. 2015, 641, 715–723, DOI: 10.1002/zaac.201400491.
  • Maurya, M. R.; Uprety, B.; Avecilla, F.; Tariq, S.; Azam, A. 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.
  • Plutín, A. M.; Alvarez, A.; Mocelo, R.; Ramos, R.; Castellano, E. E.; da Silva, M. M.; Vegas, L. C.; Pavan, F. R.; Batista, A. A. Anti-Mycobacterium tuberculosis Activity of Platinum(II)/N,N-disubstituted-N′-Acyl Thiourea Complexes. Inorg. Chem. Commun. 2016, 63, 74–80. DOI: 10.1016/j.inoche.2015.11.020.
  • Adhikari, S.; Hussain, O.; Phillips, R. M.; Kaminsky, W.; Kollipara, M. R. Neutral and Cationic Half-Sandwich Arene d6 Metal Complexes Containing Pyridyl and Pyrimidyl Thiourea Ligands with Interesting Bonding Modes: Synthesis, Structural and anti-Cancer Studies. Appl. Organometal. Chem. 2018, 32, e4476. DOI: 10.1002/aoc.4476.
  • Adhikari, S.; Hussain, O.; Phillips, R. M.; Kaminsky, W.; Kollipara, M. R. M. R. Synthesis, Structural and Chemosensitivity Studies of Arene d6 Metal Complexes Having N-phenyl-N´-(Pyridyl/Pyrimidyl)Thiourea Derivatives. Appl. Organometal. Chem. 2018, 32, e4362. DOI: 10.1002/aoc.4362.

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.