258
Views
1
CrossRef citations to date
0
Altmetric
Articles

6-Morpholino- and 6-amino-9-sulfonylpurine derivatives. Synthesis, computational analysis, and biological activity

ORCID Icon, ORCID Icon, , ORCID Icon, ORCID Icon, , ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon show all
Pages 470-503 | Received 28 Oct 2020, Accepted 23 Feb 2021, Published online: 12 Mar 2021

References

  • Kolaczek, A.; Fusiarz, I.; Lawecka, J.; Branowska, D. Biological Activity and Synthesis of Sulfonamide Derivatives: A Brief Review. Chemik 2014, 68, 620–628.
  • VanMeter, K. C.; Hubert, R. J. Microbiology for the Healthcare Professional; Elsevier: St. Louis, MO, 2016.
  • Scozzafava, A.; Briganti, F.; Mincione, G.; Menabuoni, L.; Mincione, F.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Synthesis of water-soluble, aminoacyl/dipeptidyl sulfonamides possessing long-lasting intraocular pressure-lowering properties via the topical route. J. Med. Chem. 1999, 42, 3690–3700. DOI: 10.1021/jm9901879.
  • Jaiswal, M.; Khadikar, P. V.; Supuran, C. T. Topological Modeling of Lipophilicity, Diuretic Activity, and Carbonic Inhibition Activity of benzene sulfonamides: a molecular connectivity approach. Bioorg. Med. Chem. Lett. 2004, 14, 5661–5666. DOI: 10.1016/j.bmcl.2004.08.051.
  • Nishimori, I.; Vullo, D.; Innocenti, A.; Scozzafava, A.; Mastrolorenz, A.; Supuran, C. T. Carbonic Anhydrase Inhibitors: Inhibition of the Transmembrane Isozyme XIV with Sulfonamides. Bioorg. Med. Chem. Lett. 2005, 15, 3828–3833. DOI: 10.1016/j.bmcl.2005.06.055.
  • Ogden, R. C.; Flexner, C. W. Protease Inhibitors in AIDS Therapy; Marcel Dekker: New York, Basel, 2001.
  • Casini, A.; Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Sulfonamides and Sulfonylated Derivatives as Anticancer Agents. Ccdt. 2002, 2, 55–75. DOI: 10.2174/1568009023334060.
  • Ismail, M. M.; Ghorab, M. M.; Noaman, E.; Ammar, Y. A.; Heiba, H. I.; Sayed, M. Y. Novel Synthesis of Pyrrolo[2,3-d]Pyrimidines Bearing Sulfonamide Moieties as Potential Antitumor and Radioprotective Agents. Arzneim. Forsch 2006, 56, 301–308.
  • Rostom, S. A. Synthesis and in-Vitro Antitumor Evaluation of Some Indeno [1,2-c]Pyrazol(in)es Substituted with Sulfonamide, Sulfonyl-Urea(-Thiourea) Pharmacophores, and Some Derived Thiazole Ring Systems. Bioorg. Med. Chem 2006, 14, 6475–6485. DOI: 10.1016/j.bmc.2006.06.020.
  • Supuran, C. T.; Scozzafava, A.; Mastrolorenzo, A. Bacterial Proteases: current Theraputic Use and Future Prospects for the Development of New Antibiotics. Exp. Opin. Therap. Pat 2001, 1, 221–259.
  • Scozzafava, A.; Supuran, C. T. Carbonic Anhydrase and Matrix Metalloproteinase Inhibitors: Sulfonylated Amino Acid Hydroxamates with MMP Inhibitory Properties Act as Efficient Inhibitors of CA Isozymes I, II, and IV, and N-hydroxysulfonamides inhibit both these zinc enzymes . J. Med. Chem. 2000, 43, 3677–3687. DOI: 10.1021/jm000027t.
  • Žinić, B.; Krizmanić, I.; Žinić, M. Synthesis of the sulfonylpyrimidine derivatives with anticancer activity. E.P. Patent 0 877 022 B1, April 16, 2003.
  • Saftić, D.; Vianello, R.; Žinić, B. 5-Triazolyluracils and Their N1-Sulfonyl Derivatives: Intriguing Reactivity Differences in the Sulfonation of Triazole N1′-Substituted and N1′-Unsubstituted Uracil Molecules. Eur. J. Org. Chem 2015, 35, 7695–7704.
  • Matić, J.; Nekola, I.; Višnjevac, A.; Kobetić, R.; Martin-Kleiner, I.; Kralj, M.; Žinić, B. C5-Morpholinomethylation of N1-Sulfonylcytosines by a One-Pot Microwave Assisted Mannich Reaction. Org. Biomol. Chem. 2018, 16, 2678–2687. DOI: 10.1039/c8ob00253c.
  • Glavaš-Obrovac, L.; Karner, I.; Žinić, B.; Pavelić, K. Antineoplastic Activity of Novel N-1-Sulfonypyrimidine Derivatives. Anticancer Res 2001, 21, 1979–1986.
  • Supek, F.; Kralj, M.; Marjanović, M.; Šuman, L.; Šmuc, T.; Krizmanić, I.; Žinić, B. Atypical Cytostatic Mechanism of N-1-Sulfonylcytosine Derivatives Determined by in Vitro Screening and Computational Analysis. Invest New Drugs. 2008, 26, 97–110. DOI: 10.1007/s10637-007-9084-1.
  • Glavaš-Obrovac, L.; Jukić, M.; Mišković, K.; Marković, I.; Saftić, D.; Ban, Ž.; Matić, J.; Žinić, B. Antiproliferative and Proapoptotic Activity of Molecular Copper(II) Complex of N-1-Tosylcytosine. J Trace Elem Med Biol. 2019, 55, 216–222. DOI: 10.1016/j.jtemb.2017.10.009.
  • Kašnar-Šamprec, J.; Glavaš-Obrovac, L.; Pavlak, M.; Mihaljević, I.; Štambuk, N.; Konjevoda, P.; Žinić, B. Synthesis, Spectroscopic Characterization and Biological Activity of N-1-Sulfonylcytosine Derivatives. Croat. Chem. Acta 2005, 78, 261–267.
  • Pavlak, M.; Stojković, R.; Radačić-Aumiler, M.; Kašnar-Šamprec, J.; Jerčić, J.; Vlahović, K.; Žinić, B.; Radačić, M. Antitumor Activity of Novel N-Sulfonylpyrimidine Derivatives on the Growth of Anaplastic Mammary Carcinoma in Vivo. J Cancer Res Clin Oncol. 2005, 131, 829–836. DOI: 10.1007/s00432-005-0026-z.
  • Kašnar-Šamprec, J.; Ratkaj, I.; Mišković, K.; Pavlak, M.; Baus-Lončar, M.; Kraljević Pavelić, S.; Glavaš-Obrovac, L.; Žinić, B. In Vivo Toxicity Study of N-1-Sulfonylcytosine Derivatives and Their Mechanisms of Action in Cervical Carcinoma Cell Line. Invest New Drugs. 2012, 30, 981–990. DOI: 10.1007/s10637-011-9657-x.
  • Glavaš-Obrovac, L.; Karner, I.; Štefanić, M.; Kašnar-Šamprec, J.; Žinić, B. Metabolic Effects of Novel N-1-Sulfonylpyrimidine Derivatives on Human Colon Carcinoma Cells. Farmaco 2005, 60, 479–483. DOI: 10.1016/j.farmac.2005.04.006.
  • Rossi, A. The Clinical Uses of Nucleoside Analogues in Malignant Disease. In Nucleoside Analogues: Chemistry, Biology, and Medical Applications; Walker, R.T., De Clercq, E., Eckstein, F. Eds.; Plenum Press: New York; 1979; pp. 409–436
  • Nielsen, O. H.; Vainer, B.; Rask-Madsen, J. Review article: the treatment of inflammatory bowel disease with 6-mercaptopurine or azathioprine . Aliment. Pharmacol. Ther. 2001, 15, 1699–1708. DOI: 10.1046/j.1365-2036.2001.01102.x.
  • Lukenbill, J.; Kalaycio, M. Fludarabine: A Review of the Clear Benefits and Potential Harms. Leuk. Res. 2013, 37, 986–994. DOI: 10.1016/j.leukres.2013.05.004.
  • Leclerc, M.; Suarez, F.; Noël, M. P.; Vekhoff, A.; Troussard, X.; Claisse, J. F.; Thieblemont, C.; Maloisel, F.; Beguin, Y.; Tamburini, J.; et al. Rituximab Therapy for Hairy Cell Leukemia: A Retrospective Study of 41 Cases. Ann. Hematol. 2015, 94, 89–95. DOI: 10.1007/s00277-014-2175-0.
  • Liliemark, J. The Clinical Pharmacokinetics of Cladribine. Clin. Pharmacokinet. 1997, 32, 120–131. DOI: 10.2165/00003088-199732020-00003.
  • De Clercq, E. Antiviral Drugs in Current Clinical Use. J. Clin. Virol. 2004, 30, 115–133. DOI: 10.1016/j.jcv.2004.02.009.
  • De Clercq, E.; Field, H. J. Antiviral Prodrugs - the Development of Successful Prodrug Strategies for Antiviral Chemotherapy. Br. J. Pharmacol. 2006, 147, 1–11. DOI: 10.1038/sj.bjp.0706446.
  • De Clercq, E. Milestones in the Discovery of Antiviral Agents: nucleosides and Nucleotides. Acta Pharm. Sin. B 2012, 2, 535–548. DOI: 10.1016/j.apsb.2012.10.001.
  • Laufer, S. A.; Domeyer, D. M.; Scior, T. R. F.; Albrecht, W.; Hauser, D. R. J. Synthesis and Biological Testing of Purine Derivatives as Potential ATP-Competitive Kinase Inhibitors. J. Med. Chem. 2005, 48, 710–722. DOI: 10.1021/jm0408767.
  • Endo, K.; Deguchi, K.; Matsunaga, H.; Tomaya, K.; Yamada, K. 8-Substituted 2-alkynyl-N(9)-propargyladenines as A2A adenosine receptor antagonists . Bioorg. Med. Chem. 2014, 22, 3072–3082. DOI: 10.1016/j.bmc.2014.04.041.
  • Hocek, M.; Naus, P.; Pohl, R.; Votruba, I.; Furman, P. A.; Tharnish, P. M.; Otto, M. J. Cytostatic 6-Arylpurine Nucleosides. 6. SAR in anti-HCV and Cytostatic Activity of Extended Series of 6-Hetarylpurine Ribonucleosides. J. Med. Chem. 2005, 48, 5869–5873. DOI: 10.1021/jm050335x.
  • Martirosyan, Z. A.; Gunar, V. I.; Zav′yalov, S. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1970, 1841–1844.
  • Megati, S.; Phadtare, S.; Zemlicka, J. Unsaturated Phosphonates as Acyclic Nucleotide Analogs. Anomalous Michaelis-Arbuzov and Michaelis-Becker Reactions with Multiple Bond Systems. J. Org. Chem. 1992, 57, 2320–2327. DOI: 10.1021/jo00034a025.
  • Žinić, B.; Krizmanić, I.; Vikić-Topić, D.; Srzić, D.; Žinić, M. Synthesis, NMR and MS Study of Novel N-Sulfonylated Purine Derivatives. Croat. Chem. Acta 2001, 74, 399–414.
  • Scozzafava, A.; Mastrolorenzo, A.; Supuran, C. T. Antimycobacterial Activity of 9-Sulfonylated/Sulfenylated-6-Mercaptopurine Derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 1675–1678. DOI: 10.1016/s0960-894x(01)00266-9.
  • Bakkestuen, A. K.; Gundersen, L.-L.; Utenova, B. T. Synthesis, Biological Activity, and SAR of Antimycobacterial 9-Aryl-, 9-Arylsulfonyl-, and 9-Benzyl-6-(2-Furyl)Purines. J. Med. Chem. 2005, 48, 2710–2723. DOI: 10.1021/jm0408924.
  • Kucukdumlu, A.; Tuncbilek, M.; Guven, E. B.; Atalay, R. C. Synthesis of Some Substituted 6-Phenyl Purine Analogues and Their Biological Evaluation as Cytotoxic Agents. Acta Chim Slov 2017, 64, 621–632. DOI: 10.17344/acsi.2017.3419.
  • Demir, Z.; Guven, E. B.; Ozbey, S.; Kazak, C.; Atalay, R. C.; Tuncbilek, M. Synthesis of Novel Substituted Purine Derivatives and Identification of the Cell Death Mechanism. Eur. J. Med. Chem. 2015, 89, 701–720. DOI: 10.1016/j.ejmech.2014.10.080.
  • (a) Díaz-Gavilán, M.; Gómez-Vidal, J. A.; Rodríguez-Serrano, F.; Marchal, J. A.; Caba, O.; Aránega, A.; Gallo, M. A.; Espinosa, A.; Campos, J. M. Anticancer activity of (1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl)-pyrimidines and -purines against the MCF-7 cell line: Preliminary cDNA microarray studies. Bioorg. Med. Chem. Lett. 2008, 18, 1457–1460. (b) Kode, N.; Chen, L.; Murthy, D.; Adewumi, D.; Phadtare, S. New bis-N9-(methylphenylmethyl)purine derivatives: Synthesis and antitumor activity. Eur. J. Med. Chem. 2007, 42, 327–333.
  • (a) Ikejiri, M.; Ohshima, T.; Fukushima, A.; Shimotohno K.; Maruyama, T. Synthesis and evaluation of 5′-modified 2′-deoxyadenosine analogues as anti-hepatitis C virus agents. Bioorg. Med. Chem. Lett. 2008, 18, 4638–4641. (b) Ikejiri, M.; Saijo, M.; Morikawa, S.; Fukushi, S.; Mizutani, T.; Kurane I.; Maruyama, T. Synthesis and biological evaluation of nucleoside analogues having 6-chloropurine as anti-SARS-CoV agents. Bioorg. Med. Chem. Lett. 2007, 17, 2470–2473. (c) Maruyama, T.; Sato, Y.; Oto, Y.; Takahashi, Y.; Snoeck, R.; Andrei, G.; Witvrouw, M.; De Clercq, E. Synthesis and antiviral activity of 6-chloropurine arabinoside and its 2'-deoxy-2'-fluoro derivative. Chem. Pharm. Bull. 1996, 44, 2331–2334.
  • Aleksandrova, E. V.; Kochergin, P. M. The Use of Protecting Groups in the Synthesis of Purine Derivatives (Review). Chem. Heterocycl. Comp. 2009, 45, 1–27. DOI: 10.1007/s10593-009-0220-z.
  • Jain, Z. J.; Gide, P. S.; Kankate, R. S. Biphenyls and Their Derivatives as Synthetically and Pharmacologically Important Aromatic Structural Moieties. Arab. J. Chem 2017, 10, S2051–S2066. DOI: 10.1016/j.arabjc.2013.07.035.
  • Tarade, D.; Ma, D.; Pignanelli, C.; Mansour, F.; Simard, D.; van den Berg, S.; Gauld, J.; McNulty, J.; Pandey, S. Structurally Simplified Biphenyl Combretastatin A4 Derivatives Retain in Vitro anti-cancer activity dependent on mitotic arrest. PLoS One. 2017, 12, e0171806. DOI: 10.1371/journal.pone.0171806.
  • Benfodda, Z.; Fritz, V.; Henriquet, C.; Fattorusso, C.; Cebrián-Torrejón, G.; Persico, M.; Di Dato, A.; Menna, M.; Blancou, H.; Fajas, L. Synthesis, Anticancer Activity and Computational SAR Analysis of Acylsulfonylpiperazines Derivatives. Med. Chem. (Los Angeles) 2017, 7, 257–267.
  • Fernández-Tornero, C.; Lozano, R. M.; Redondo-Horcajo, M.; Gómez, A. M.; López, J. C.; Quesada, E.; Uriel, C.; Valverde, S.; Cuevas, P.; Romero, A.; Giménez-Gallego, G. Leads for Development of New Naphthalenesulfonate Derivatives with Enhanced Antiangiogenic Activity: cristal Structure of Acidic Fibroblast Growth Factor in Complex with 5-Amino-2-Naphathalenesulfonate. J. Biol. Chem 2003, 278, 21774–21781. DOI: 10.1074/jbc.M212833200.
  • Mishra, R. C.; Gundala, S. R.; Karna, P.; Lopus, M.; Gupta, K. K.; Nagaraju, M.; Hamelberg, D.; Tandon, V.; Panda, D.; Reid, M. D.; Aneja, R. Design, Synthesis and Biological Evaluation of Disubstituted Noscapine Analogs as Potent and Microtubule-Targeted Anticancer Agents. Bioorg. Med. Chem. Lett 2015, 25, 2133–2140. DOI: 10.1016/j.bmcl.2015.03.076.
  • Ferenc, G.; Pádár, P.; Szolomájer, J.; Kovács, L. N-Alkylated Guanine Derivatives. Coc. 2009, 13, 1085–1135. DOI: 10.2174/138527209788680718.
  • Zhong, M.; Robins, M. J. Regiospecific N9 Alkylation of 6-(heteroaryl)purines: shielding of N7 by a proximal heteroaryl C-H1. J. Org. Chem. 2006, 71, 8901–8906. DOI: 10.1021/jo061759h.
  • Meshram, G. A.; Patil, V. D. A Simple and Efficient Method for Sulfonylation of Amines, Alcohols and Phenols with Cupric Oxide under Mild Conditions. Tetrahedron Lett 2009, 50, 1117–1121. DOI: 10.1016/j.tetlet.2008.12.085.
  • Brik, A.; Wu, C.-Y.; Best, M. D.; Wong, C.-H. Tetrabutylammonium Fluoride-Assisted Rapid N9-Alkylation on Purine Ring: application to Combinatorial Reactions in Microtiter Plates for the Discovery of Potent Sulfotransferase Inhibitors in Situ. Bioorg. Med. Chem. 2005, 13, 4622–4626. DOI: 10.1016/j.bmc.2005.02.066.
  • Al-Ghorbani, M.; Begum, B. A.; Zabiulla, S.; Mamatha, S. V.; Khanum, S. A. Piperazine and Morpholine: Synthetic Preview and Pharmaceutical Applications. J. Chem. Pharm. Res 2015, 7, 281–301.
  • Huang, L.-K.; Cherng, Y.-C.; Cheng, Y.-R.; Jang, J.-P.; Chao, Y.-L.; Cherng, Y.-J. An Efficient Synthesis of Substituted Cytosines and Purines under Focused Microwave Irradiation. Tetrahedron 2007, 63, 5323–5327. DOI: 10.1016/j.tet.2007.02.124.
  • Hanus, M.; Kabeláč, M.; Rejnek, J.; RyjáčEk, F.;.; Hobza, P. ; Correlated ab Initio Study of Nucleic Acid Bases and Their Tautomers in the Gas Phase, in a Microhydrated Environment, and in Aqueous Solution. Part 3. Adenine. J. Phys. Chem. B. 2004, 108, 2087–2097. DOI: 10.1021/jp036090m.
  • Tandarić, T.; Vianello, R. Design of Exceptionally Strong Organic Superbases Based on Aromatic Pnictogen Oxides: Computational DFT Analysis of the Oxygen Basicity in the Gas Phase and Acetonitrile Solution. J. Phys. Chem. A. 2018, 122, 1464–1471. DOI: 10.1021/acs.jpca.7b11945.
  • Despotović, I.; Vianello, R. Engineering Exceptionally Strong Oxygen Superbases with 1,8-Diazanaphthalene di-N-Oxides. Chem Commun (Camb) .) 2014, 50, 10941–10944. DOI: 10.1039/c4cc05125d.
  • Hansch, C.; Leo, A.; Taft, R. W. A Survey of Hammett Substituent Constants and Resonance and Field Parameters. Chem. Rev. 1991, 91, 165–195. DOI: 10.1021/cr00002a004.
  • Zask, A.; Verheijen, J. C.; Richard, D. J. Recent Advances in the Discovery of Small-Molecule ATP Competitive mTOR Inhibitors: A Patent Review. Expert Opin Ther Pat 2011, 21, 1109–1127. DOI: 10.1517/13543776.2011.584871.
  • Chen, Y.; Wang, X.; Xiang, W.; He, L.; Tang, M.; Wang, F.; Wang, T.; Yang, Z.; Yi, Y.; Wang, H.; et al. Development of Purine-Based Hydroxamic Acid Derivatives: Potent Histone Deacetylase Inhibitors with Marked in Vitro and in Vivo Antitumor Activities. J. Med. Chem. 2016, 59, 5488–5504. DOI: 10.1021/acs.jmedchem.6b00579.
  • Long, Y.; Yu, M.; Li, P.; Islam, S.; Goh, A. W.; Kumarasiri, M.; Wang, S. Synthesis and Biological Evaluation of Heteroaryl Styryl Sulfone Derivatives as Anticancer Agents. Bioorg. Med. Chem. Lett. 2016, 26, 5674–5678. DOI: 10.1016/j.bmcl.2016.10.062.
  • Haneef, J.; Parvathy, M.; M. P.; Thankayyan R, S. K.; Sithul, H.; Sreeharshan, S. Bax translocation mediated mitochondrial apoptosis and caspase dependent photosensitizing effect of Ficus religiosa on cancer cells. PloS ONE 2012, 7, e40055. DOI: 10.1371/annotation/ab341223-61ed-4b19-95c7-21455c321e06.
  • Mojzych, M.; Šubertová, V.; Bielawska, A.; Bielawski, K.; Bazgier, V.; Berka, K.; Gucký, T.; Fornal, E.; Kryštof, V. Synthesis and Kinase Inhibitory Activity of New Sulfonamide Derivatives of Pyrazolo[4,3-e][1,2,4]Triazines. Eur. J. Med. Chem 2014, 78, 217–224. DOI: 10.1016/j.ejmech.2014.03.054.
  • Wang, Q.; Su, L.; Liu, N.; Zhang, L.; Xu, W.; Fang, H. Cyclin Dependent Kinase 1 Inhibitors: A Review of Recent Progress. Curr. Med. Chem. 2011, 18, 2025–2043. DOI: 10.2174/092986711795590110.
  • , Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H, Gaussian 16, Revision C.01 Gaussian, Inc., Wallingford CT, 2016.
  • Cindrić, M.; Sović, I.; Mioč, M.; Hok, L.; Boček, I.; Roškarić, P.; Butković, K.; Martin-Kleiner, I.; Starčević, K.; Vianello, R.; et al. Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole/Benzothiazole-2-Carboxamides with Antiproliferative Activity. Antioxidants 2019, 8, 477. DOI: 10.3390/antiox8100477.
  • Tandarić, T.; Hok, L.; Vianello, R. From Hydrogen Peroxide-Responsive Boronated Nucleosides towards Antisense Therapeutics – a Computational Mechanistic Study. Croat. chem. Acta. (Online) 2019, 92, 287–295. DOI: 10.5562/cca3592.
  • Pantalon Juraj, N.; Muratović, S.; Perić, B.; Šijaković Vujičić, N.; Vianello, R.; Žilić, D.; Jagličič, Z.; Kirin, S. I. Structural Variety of Isopropyl-Bis(2-Picolyl)Amine Complexes with Zinc(II) and Copper(II). Cryst. Growth Des 2020, 20, 2440–2453. DOI: 10.1021/acs.cgd.9b01625.
  • Pantalon Juraj, N.; Miletić, G. I.; Perić, B.; Popović, Z.; Smrečki, N.; Vianello, R.; Kirin, S. I. Stereochemistry of Hexacoordinated Zn(II), Cu(II), Ni(II), and Co(II) Complexes with Iminodiacetamide Ligands. Inorg. Chem. 2019, 58, 16445–16457. DOI: 10.1021/acs.inorgchem.9b02200.
  • Tandarić, T.; Vianello, R. Computational Insight into the Mechanism of the Irreversible Inhibition of Monoamine Oxidase Enzymes by the Antiparkinsonian Propargylamine Inhibitors Rasagiline and Selegiline. ACS Chem Neurosci 2019, 10, 3532–3542. DOI: 10.1021/acschemneuro.9b00147.
  • Maršavelski, A.; Vianello, R. What a Difference a Methyl Group Makes: The Selectivity of Monoamine Oxidase B Towards Histamine and N-Methylhistamine. Chemistry 2017, 23, 2915–2925. DOI: 10.1002/chem.201605430.
  • Mickisch, G.; Fajta, S.; Bier, H.; Tschada, R.; Alken, P. Cross-Resistance Patterns Related to Glutathione Metabolism in Primary Human Renal Cell Carcinoma. Urol. Res. 1991, 19, 99–103. DOI: 10.1007/BF00368184.
  • Badisa, R. B.; Darling-Reed, S. F.; Joseph, P.; Cooperwood, J. S.; Latinwo, L. M.; Goodman, C. B. Selective Cytotoxic Activities of Two Novel Synthetic Drugs on Human Breast Carcinoma MCF-7 Cells. Anticancer Res. 2009, 29, 2993–2996.

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.