Synthesis and Biological Evaluation of Novel Phenothiazine Derivatives as Potential Antitumor Agents

References

• Berntsen, “Ueber das methylenblau,” Berichte Der Deutschen Chemischen Gesellschaft 16, (1883): 1025–8.
   Google Scholar
• A. D. Mosnaim, V. V. Ranade, M. E. Wolf, J. Puente, and V. M. Antonieta, “Phenothiazine Molecule Provides the Basic Chemical Structure for Various Classes of Pharmacotherapeutic Agents,” American Journal of Therapeutics 13, no. 3 (2006): 261–73.
   PubMedGoogle Scholar
• Z. S. Huang, H. Meier, and D. Cao, “Phenothiazine-Based Dyes for Efficient Dye-Sensitized Solar Cells,” Journal of Materials Chemistry C 4, no. 13 (2016): 2404–26.
   Web of Science ®Google Scholar
• J. Al-Busaidi, A. Haque, N. K. Al Rasbi, and M. S. Khan, “Phenothiazine-Based Derivatives for Optoelectronic Applications: A Review,” Synthetic Metals 257, (2019): 116189.
   Web of Science ®Google Scholar
• S. S. Deshpande, H. S. Kumbhar, and G. S. Shankarling, “Solvatochromic Fluorescence Properties of Phenothiazine-Based Dyes Involving Thiazolo[4,5-b]quinoxaline and Benzo[e]indole as Strong Acceptors,” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 174, (2017): 154–63.
   PubMed Web of Science ®Google Scholar
• W. Wang, J. Y. Ning, J. T. Liu, J. Y. Miao, and B. X. Zhao, “A Mitochondria-Targeted Ratiometric Fluorescence Sensor for the Detection of Hypochlorite in Living Cells,” Dyes and Pigments 171, (2019): 107708–11.
   Web of Science ®Google Scholar
• W. Sheng, X. Shen, X. Yue and C. Huang CN Pat. 108250220A, 2018.
   Google Scholar
• A. Eriksson, J. Yachnin, R. Lewensohn, A. Nilsson, and A. Nilsso, “DNA-Dependent Protein Kinase is Inhibited by Trifluoperazine,” Biochemical and Biophysical Research Communications 283, no. 4 (2001): 726–31.
   PubMed Web of Science ®Google Scholar
• A. Ghinet, I. M. Moise, B. Rigo, G. Homerin, A. Farce, J. Dubois, and E. Bicu, “Studies on Phenothiazines: New Microtubule-Interacting Compounds with Phenothiazine A-Ring as Potent Antineoplastic Agents,” Bioorganic & Medicinal Chemistry 24, no. 10 (2016): 2307–17.
   PubMed Web of Science ®Google Scholar
• Leonard Amaral, and Miguel Viveiros, “Thioridazine: A Non-Antibiotic Drug Highly Effective, in Combination with First Line anti-Tuberculosis Drugs, against Any Form of Antibiotic Resistance of mycobacterium tuberculosis Due to Its Multi-Mechanisms of Action,” Antibiotics 6, no. 1 (2017): 3–14.
   Google Scholar
• S. P. Massie, “The Chemistry of Phenothiazine,” Chemical Reviews 54, no. 5 (1954): 797–833.
   Web of Science ®Google Scholar
• A. J. Warman, T. S. Rito, N. E. Fisher, D. M. Moss, N. G. Berry, P. M. O'Neill, S. A. Ward, and G. A. Biagini, “Antitubercular Pharmacodynamics of Phenothiazines,” The Journal of Antimicrobial Chemotherapy 68, no. 4 (2013): 869–80.
   PubMed Web of Science ®Google Scholar
• T. N. Tozer, L. D. Tuck, and J. C. Craig, “The Activity of Phenothiazine Anthelmintics as Related to Semiquinone Formation,” Journal of Medicinal Chemistry 12, no. 2 (1969): 294–9.
   PubMed Web of Science ®Google Scholar
• Gabriela P. Sarmiento, M. Florencia Martini, Roxana G. Vitale, Lucas E. Fabian, Javier Afeltra, Daniel Vega, Graciela Y. Moltrasio, and Albertina G. Moglioni, “N-Haloacetyl Phenothiazines and Derivatives: Preparation, Characterization and Structure-Activity Relationship for Antifungal Activity,” Arabian Journal of Chemistry 12, no. 1 (2019): 21–32.
   Web of Science ®Google Scholar
• Martha Kalkanidis, Nectarios Klonis, Leann Tilley, and Leslie W. Deady, “Novel Phenothiazine Antimalarials: Synthesis, Antimalarial Activity, and Inhibition of the Formation of b-Haematin,” Biochemical Pharmacology 63, no. 5 (2002): 833–42.
   PubMed Web of Science ®Google Scholar
• J. M. Wilson, S. Sanyal, and H. H. Van Tol, “Dopamine D2 and D4 Receptor Ligands: Relation to Antipsychotic Action,” European Journal of Pharmacology 351, no. 3 (1998): 273–86.
   PubMed Web of Science ®Google Scholar
• H. Maurer, and K. Pfleger, “Identification of Phenothiazine Antihistamines and Their Metabolites in Urine,” Archives of Toxicology 62, no. 2–3 (1988): 185–91.
   PubMed Web of Science ®Google Scholar
• C. Montoya, L. D. Done, R. F. Heier, M. J. Meyers, and D. J. Krysan, “Antifungal Phenothiazines: Optimization, Characterization of Mechanism, and Modulation of Neuroreceptor Activity,” ACS Infectious Diseases 4, no. 4 (2018): 499–507.
   PubMed Web of Science ®Google Scholar
• Beata Morak-Młodawska, Krystian Pluta, Małgorzata Latocha, and Małgorzata Jeleń, “Synthesis, Spectroscopic Characterization, and Anticancer Activity of New 10-Substituted 1,6-Diazaphenothiazines,” Medicinal Chemistry Research : An International Journal for Rapid Communications on Design and Mechanisms of Action of Biologically Active Agents 25, no. 11 (2016): 2425–33.
   PubMed Web of Science ®Google Scholar
• K. Venkatesan, V. S. V. Satyanarayana, K. Mohanapriya, S. S. Khora, and A. Sivakumar, “Ultrasound-Mediated Synthesis of Phenothiazine Derivatives and Their in Vitro Antibacterial and Antioxidant Studies,” Research on Chemical Intermediates 41, no. 2 (2015): 595–607.
   Web of Science ®Google Scholar
• Justyna B. Mocko, Andreas Kern, Bernd Moosmann, Christian Behl, and Parvana Hajieva, “Phenothiazines Interfere with Dopaminergic Neurodegeneration in Caenorhabditis elegans Models of Parkinson's Disease,” Neurobiology of Disease 40, no. 1 (2010): 120–9.
   PubMed Web of Science ®Google Scholar
• F. DeEds, and J. O. Thomas, “Studies on Phenothiazine. XI. The Excretion of Phenothiazone,” The Journal of Parasitology 28, no. 5 (1942): 363–7.
   Google Scholar
• N. Motohashi, M. Kawase, S. Saito, and H. Sakagami, “Antitumor Potential and Possible Targets of Phenothiazine-Related Compounds,” Current Drug Targets 1, no. 3 (2000): 237–46.
   PubMedGoogle Scholar
• C. H. Wu, L. Y. Bai, M. H. Tsai, P. C. Chu, C. F. Chiu, M. Y. Chen, S. J. Chiu, J. H. Chiang, and J. R. Weng, “Pharmacological Exploitation of the Phenothiazine Antipsychotics to Develop Novel Antitumor Agents-A Drug Repurposing Strategy,” Scientific Reports 6, no. 1 (2016): 27540–11.
   PubMedGoogle Scholar
• N. Gautam, A. Garg, A. K. Bishnoi, S. Agarwal, and D. C. Gautam, “Antioxidant and Antimicrobial Assessment of Synthesized and Spectrally Characterized New Nitrophenothiazines and Their Sulfone Analogues,” Phosphorus, Sulfur, and Silicon and the Related Elements 190, no. 4 (2015): 528–36.
   Web of Science ®Google Scholar
• N. Gautam, S. Gupta, N. Ajmera, and D. C. Gautam, “Synthesis, Characterization, and Biological Evaluation of 10H-Phenothiazines, Their Sulfones and Ribofuranosides,” Journal of Heterocyclic Chemistry 49, no. 3 (2012): 710–5.
   Web of Science ®Google Scholar
• N. Gautam, N. Ajmera, S. Gupta, P. Meena, A. Kumar, and D. C. Gautam, “Synthesis and Pharmacological Use of 10H-Phenothiazines,” Their Sulfones, and Ribofuranosides” Phosphorus, Sulfur, and Silicon and the Related Elements 185, no. 12 (2010): 2409–17.
   Web of Science ®Google Scholar
• N. Gautam, N. Ajmera, S. Gupta, and D. C. Gautam, “Synthesis, Spectral Characterization, and Biological Activity of Some New Substituted 10H-Phenothiazines, Its Ribofuranosides, and Sulfones,” Nucleosides, Nucleotides & Nucleic Acids 29, no. 3 (2010): 178–89.
   PubMed Web of Science ®Google Scholar
• N. Motohashi, S. R. Gollapudi, J. Emrani, and K. R. Bhattiprolu, “Antitumor Properties of Phenothiazines,” Cancer Investigation 9, no. 3 (1991): 305–19.
   PubMed Web of Science ®Google Scholar
• G. Spengler, A. Csonka, J. Molnar, and L. Amaral, “The Anticancer Activity of the Old Neuroleptic Phenothiazine-Type Drug Thioridazine,” Anticancer Research 36, no. 11 (2016): 5701–6.
   PubMed Web of Science ®Google Scholar
• Q. Lu, and D. YanQing, “Potential Antitumor Mechanisms of Phenothiazine Drugs,” Science China. Life Sciences 56, no. 11 (2013): 1020–7.
   PubMed Web of Science ®Google Scholar
• R. Sivaramakarthikeyan, S. Iniyaval, K. Padmavathy, L. Hui-Shan, L. Chin-King, M. Chun-Wai, and C. Ramalingan, “Phenothiazine and Amide-Ornamented Dihydropyridines via a Molecular Hybridization Approach: Design, Synthesis, Biological Evaluation and Molecular Docking Studies,” New Journal of Chemistry 43, no. 43 (2019): 17046–57.
   Web of Science ®Google Scholar
• J. I. Ahamed, M. F. Valan, K. Pandurengan, P. Agastian, B. Venkatadri, M. R. Rameshkumar, and K. Narendran, “A Novel Method for the Synthesis and Characterization of 10‑Hexyl‑3‑(1‑Hexyl‑4,5‑Diphenyl‑1H‑Imidazol‑2‑yl)‑10H‑ Phenothiazine: DFT Computational, in Vitro Anticancer and in Silico Molecular Docking Studies,” Research on Chemical Intermediates 47, no. 2 (2021): 759–94.
   Web of Science ®Google Scholar
• M. D. Shanti, K. D. Shanti, J. Meshram, M. Raut, and K. Nandekar, “Design, Synthesis and Bio-Evaluation of New Phenothiazine Derivatives of Sulfonamide Dyes as Anticancer Agents,” Advanced Materials Proceedings 5, no. 3 (2021): 1–6.
   Google Scholar
• N. Manav, V. Verma, V. Pandey, H. Rather, R. Vasita, and I. Gupta, “Synthesis and Studies of Phenothiazine Based AIE Fluorogens,” Indian Journal of Chemistry -Section B 58, (2019): 238–46.
   Web of Science ®Google Scholar
• K. Venkatesan, V. S. V. Satyanarayana, A. Sivakumar, C. Ramamurthy, and C. Thirunavukkarusu, “Synthesis, Spectral Characterization and Antitumor Activity of Phenothiazine Derivatives,” Journal of Heterocyclic Chemistry 57, no. 7 (2020): 2722–8.
   Web of Science ®Google Scholar