Synthesis of novel bis- and poly(aryldiazenylthiazoles)

References

• Palanimuthu, D.; Poon, R.; Sahni, S.; Anjum, R.; Hibbs, D.; Lin, H. Y.; Bernhardt, P. V.; Kalinowski, D. S.; Richardson, D. R. A Novel Class of Thiosemicarbazones Show Multi-Functional Activity for the Treatment of Alzheimer’s Disease. Eur. J. Med. Chem. 2017, 139, 612–632. DOI: 10.1016/j.ejmech.2017.08.021.
   PubMed Web of Science ®Google Scholar
• Serda, M.; Kalinowski, D. S.; Rasko, N.; Potůčková, E.; Mrozek-Wilczkiewicz, A.; Musiol, R.; Małecki, J. G.; Sajewicz, M.; Ratuszna, A.; Muchowicz, A. Exploring the anti-Cancer Activity of Novel Thiosemicarbazones Generated through the Combination of Retro-Fragments: Dissection of Critical Structure-Activity Relationships. PLoS One 2014, 9, e110291. DOI: 10.1371/journal.pone.0110291.
   PubMed Web of Science ®Google Scholar
• Kalinowski, D. S.; Quach, P.; Richardson, D. R. Thiosemicarbazones: The New Wave in Cancer Treatment. Future Med. Chem. 2009, 1, 1143–1151. DOI: 10.4155/fmc.09.80.
   PubMed Web of Science ®Google Scholar
• Aly, A. A.; Hassan, A. A.; AbdEl-Latief, E.-S. S. S. M. An Update of the Use of Thiocarbohydrazides and Thiosemicarbazides in the Preparation of Heterocycles and Their Biological Importance. J. Heterocyclic Chem. 2018, 55, 2196–2223. DOI: 10.1002/jhet.3295.
   Web of Science ®Google Scholar
• Metwally, M. A.; Bondock, S.; El-Azap, H.; Kandeel, E. E. M. Thiosemicarbazides: Synthesis and Reactions. J. Sulfur Chem. 2011, 32, 489–519. DOI: 10.1080/17415993.2011.601869.
   Web of Science ®Google Scholar
• Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; Gee, A. D.; Heslop, J. M. Acetylacetonate Bis(Thiosemicarbazone) Complexes of Copper and Nickel: Towards New Copper Radiopharmaceuticals. Dalton Trans. 2004, 2404–2412. DOI: 10.1039/b406429a.
   PubMed Web of Science ®Google Scholar
• Tarasconi, P.; Capacchi, S.; Pelosi, G.; Cornia, M.; Albertini, R.; Bonati, A.; Dall'Aglio, P. P.; Lunghi, P.; Pinelli, S. Synthesis, Spectroscopic Characterization and Biological Properties of New Natural Aldehydes Thiosemicarbazones. Bioorganic Med. Chem. 2000, 8, 157–162. DOI: 10.1016/S0968-0896(99)00260-6.
   PubMed Web of Science ®Google Scholar
• M. Riyadh, S.; M. Gomha, S.; A. Mahmmoud, E. Utility of Ethylidenethiosemicarbazides in Heterocyclic Synthesis. Cos. 2017, 14, 3–21. DOI: 10.2174/1570179413666151218202004.
   Web of Science ®Google Scholar
• Shaaban, M.; Elwahy, A. Synthesis of Oxazolo-, Thiazolo-, Pyrazolo-, and Imidazo-Fused Heterocycles by Multi-Component Reactions (Part 2). Cos. 2014, 11, 471–525. DOI: 10.2174/15701794113106660076.
   Web of Science ®Google Scholar
• Chhabria, M. T.; Patel, S.; Brahmkshatriya, P. M.; Thiazole, P. S. A Review on Chemistry, Synthesis and Therapeutic Importance of Its Derivatives. Ctmc. 2016, 16, 2841–2862. DOI: 10.2174/1568026616666160506130731.
   Web of Science ®Google Scholar
• Chen, C.; Song, J.; Wang, J.; Xu, C.; Chen, C.; Gu, W.; Sun, H.; Wen, X. Synthesis and Biological Evaluation of Thiazole Derivatives as Novel USP7 Inhibitors. Bioorganic Med. Chem. Lett. 2017, 27, 845–849. DOI: 10.1016/j.bmcl.2017.01.018.
   PubMed Web of Science ®Google Scholar
• Kesicki, E. A.; Bailey, M. A.; Ovechkina, Y.; Early, J. V.; Alling, T.; Bowman, J.; Zuniga, E. S.; Dalai, S.; Kumar, N.; Masquelin, T.; et al. Synthesis and Evaluation of the 2-Aminothiazoles as anti-Tubercular Agents. PLoS One 2016, 11, e0155209. DOI: 10.1371/journal.pone.0155209.
   PubMed Web of Science ®Google Scholar
• Aggarwal, R.; Kumar, S.; Kaushik, P.; Kaushik, D.; Gupta, G. K. Synthesis and Pharmacological Evaluation of Some Novel 2-(5-Hydroxy-5-Trifluoromethyl-4,5-Dihydropyrazol-1-Yl)-4-(Coumarin-3-Yl)Thiazoles. Eur. J. Med. Chem. 2013, 62, 508–514. DOI: 10.1016/j.ejmech.2012.11.046.
   PubMed Web of Science ®Google Scholar
• Helal, M. H. M.; Salem, M. A.; El-Gaby, M. S. A.; Aljahdali, M. Synthesis and Biological Evaluation of Some Novel Thiazole Compounds as Potential anti-Inflammatory Agents. Eur. J. Med. Chem. 2013, 65, 517–526. DOI: 10.1016/j.ejmech.2013.04.005.
   PubMed Web of Science ®Google Scholar
• Karuvalam, R. P.; Haridas, K. R.; Nayak, S. K.; Guru Row, T. N.; Rajeesh, P.; Rishikesan, R.; Kumari, N. S. Design, Synthesis of Some New (2-Aminothiazol-4-Yl)Methylester Derivatives as Possible Antimicrobial and Antitubercular Agents. Eur. J. Med. Chem. 2012, 49, 172–182. DOI: 10.1016/j.ejmech.2012.01.008.
   PubMed Web of Science ®Google Scholar
• Badiger, N. P.; Khan, A.; Kalashetti, M. B.; Khazi, I. M. Synthesis and Local Anaesthetic Activities of 2-Aminothiazole/Thiadiazole Analogues of Lidocaine. Med. Chem. Res. 2012, 21, 1544–1549. DOI: 10.1007/s00044-011-9659-4.
   Web of Science ®Google Scholar
• Cohen, A.; Verhaeghe, P.; Crozet, M. D.; Hutter, S.; Rathelot, P.; Vanelle, P.; Azas, N. Tandem Synthesis and in Vitro Antiplasmodial Evaluation of New Naphtho[2,1-d]Thiazole Derivatives. Eur. J. Med. Chem. 2012, 55, 315–324. DOI: 10.1016/j.ejmech.2012.07.034.
   PubMed Web of Science ®Google Scholar
• Liaras, K.; Geronikaki, A.; Glamočlija, J.; Ćirić, A.; Soković, M. Thiazole-Based Chalcones as Potent Antimicrobial Agents. Synthesis and Biological Evaluation. Bioorganic Med. Chem. 2011, 19, 3135–3140. DOI: 10.1016/j.bmc.2011.04.007.
   PubMed Web of Science ®Google Scholar
• Omar, K.; Geronikaki, A.; Zoumpoulakis, P.; Camoutsis, C.; Soković, M.; Ćirić, A.; Glamočlija, J. Novel 4-Thiazolidinone Derivatives as Potential Antifungal and Antibacterial Drugs. Bioorganic Med. Chem. 2010, 18, 426–432. DOI: 10.1016/j.bmc.2009.10.041.
   PubMed Web of Science ®Google Scholar
• Karthikeyan, M. S. Synthesis, Analgesic, anti-Inflammatory and Antimicrobial Studies of 2,4-Dichloro-5-Fluorophenyl Containing Thiazolotriazoles. Eur. J. Med. Chem. 2009, 44, 827–833. DOI: 10.1016/j.ejmech.2008.04.022.
   PubMed Web of Science ®Google Scholar
• Lu, Y.; Li, C.-M.; Wang, Z.; Ross, C. R.; Chen, J.; Dalton, J. T.; Li, W.; Miller, D. D. Discovery of 4-Substituted Methoxybenzoyl-Aryl-Thiazole as Novel Anticancer Agents: Synthesis, Biological Evaluation, and Structure-Activity Relationships. J. Med. Chem. 2009, 52, 1701–1711. DOI: 10.1021/jm801449a.
   PubMed Web of Science ®Google Scholar
• Fox, L. M.; Saravolatz, L. D. Nitazoxanide: A New Thiazolide Antiparasitic Agent. Clin. Infect. Dis. 2005, 40, 1173–1180. DOI: 10.1086/428839.
   PubMed Web of Science ®Google Scholar
• Cuenca-Estrella, M.; Gomez-Lopez, A.; Mellado, E.; Garcia-Effron, G.; Rodriguez-Tudela, J. L. In Vitro Activities of Ravuconazole and Four Other Antifungal Agents against Fluconazole-Resistant or -Susceptible Clinical Yeast Isolates. Antimicrob. Agents Chemother. 2004, 48, 3107–3111. DOI: 10.1128/AAC.48.8.3107-3111.2004.
   PubMed Web of Science ®Google Scholar
• Barreca, M. L.; Balzarini, J.; Chimirri, A.; E. De, C.; L. De, L.; Ho, H. D.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Rao, A.; et al. Design, Synthesis, Structure - Activity Relationships, and Molecular Modeling Studies of 2, 3-Diaryl-1, 3-Thiazolidin-4-Ones as Potent anti-HIV Agents. J. Med. Chem. 2002, 45, 5410–5413. DOI: 10.1021/JM020977+.
   PubMed Web of Science ®Google Scholar
• Agarwal, S.; Kalal, P.; Gandhi, D.; Prajapat, P. Thiazole Containing Heterocycles with CNS Activity. Cddt. 2018, 15, 178–195. DOI: 10.2174/1570163814666170724170152.
   Google Scholar
• Dini, D.; Calvete, M. J. F.; Hanack, M. Nonlinear Optical Materials for the Smart Filtering of Optical Radiation. Chem. Rev. 2016, 23, 13043–13233. pp DOI: 10.1021/acs.chemrev.6b00033.
   Web of Science ®Google Scholar
• Deckers, S.; Vandendriessche, S.; Cornelis, D.; Monnaie, F.; Koeckelberghs, G.; Asselberghs, I.; Verbiest, T.; Van Der Veen, M. A. Poly(3-Alkylthiophene)s Show Unexpected Second-Order Nonlinear Optical Response. Chem. Commun. 2014, 50, 2741–2743. DOI: 10.1039/C3CC48099B.
   PubMed Web of Science ®Google Scholar
• Salem, M. E.; Darweesh, A. F.; Farag, A. M.; Elwahy, A. H. M. 2-Bromo-1-(1H-Pyrazol-4-Yl)Ethanone: Versatile Precursors for Novel Mono-, Bis- and Poly{6-(1H-Pyrazol-4-Yl)-[1,2,4]Triazolo[3,4-b][1,3,4]Thiadiazines}. Tetrahedron 2016, 72, 712–719. DOI: 10.1016/j.tet.2015.12.024.
   Web of Science ®Google Scholar
• Salem, M. E.; Darweesh, A. F.; Mekky, A. E. M.; Farag, A. M.; Elwahy, A. H. M. 2-Bromo-1-(1H-Pyrazol-4-Yl)Ethanone: Versatile Precursor for Novel Mono- and Bis[Pyrazolylthiazoles]. J. Heterocyclic Chem. 2017, 54, 226–234. DOI: 10.1002/jhet.2571.
   Web of Science ®Google Scholar
• Salem, M. E.; Darweesh, A. F.; Farag, A. M.; Elwahy, A. H. M. Synthesis and Structures of Novel Multi-Armed Molecules Involving Benzene as a Core and 4-Phenylthiazole, 4-Pyrazolylthiazole, or Thiadiazole Units as Arms. J. Heterocyclic Chem. 2017, 54, 586–595. DOI: 10.1002/jhet.2629.
   Web of Science ®Google Scholar
• El-Fatah, N. A. A.; Darweesh, A. F.; Mohamed, A. A.; Abdelhamid, I. A.; Elwahy, A. H. M. Regioselective Synthesis and Theoretical Studies of Novel Bis(Tetrahydro[1,2,4]Triazolo[5,1-b]Quinazolin-8(4H)-Ones) Catalyzed by ZnO Nanoparticles. Monatsh. Chem. 2017, 148, 2107–2122. DOI: 10.1007/s00706-017-2040-7.
   Web of Science ®Google Scholar
• Salama, S. K.; Darweesh, A. F.; Abdelhamid, I. A.; Elwahy, A. H. M. Microwave Assisted Green Multicomponent Synthesis of Novel Bis(2-Amino-Tetrahydro-4H-Chromene-3-Carbonitrile) Derivatives Using Chitosan as Eco-Friendly Basic Catalyst. J. Heterocyclic Chem. 2017, 54, 305–312. DOI: 10.1002/jhet.2584.
   Web of Science ®Google Scholar
• Abd El-Fatah, N. A.; Darweesh, A. F.; Mohamed, A. A.; Abdelhamid, I. A.; Elwahy, A. H. M. Experimental and Theoretical Study on the Regioselective Bis- and Polyalkylation of 2-Mercaptonicotinonitrile and 2-Mercaptopyrimidine-5-Carbonitrile Derivatives. Tetrahedron 2017, 73, 1436–1450. DOI: 10.1016/j.tet.2017.01.047.
   Web of Science ®Google Scholar
• Diab, H. M.; Abdelhamid, I. A.; Elwahy, A. H. M. ZnO-Nanoparticles-Catalyzed Synthesis of Poly(Tetrahydrobenzimidazo[2,1- b] Quinazolin-1(2 H)-Ones) as Novel Multi-Armed Molecules. Synlett 2018, 29, 1627–1633. DOI: 10.1055/s-0037-1609967.
   Web of Science ®Google Scholar
• Mohamed, M. F.; Darweesh, A. F.; Elwahy, A. H. M.; Abdelhamid, I. A. Synthesis, Characterization and Antitumor Activity of Novel Tetrapodal 1,4-Dihydropyridines: P53 Induction, Cell Cycle Arrest and Low Damage Effect on Normal Cells Induced by Genotoxic Factor H2O2. RSC Adv. 2016, 6, 40900–40910. DOI: 10.1039/C6RA04974E.
   Web of Science ®Google Scholar
• Facchinetti, V.; Avellar, M. M.; Nery, A. C. S.; Gomes, C. R. B.; Vasconcelos, T. R. A.; De Souza, M. V. N. An Eco-Friendly, Hantzsch-Based, Solvent-Free Approach to 2-Aminothiazoles and 2-Aminoselenazoles. Synth 2016, 48, 437–440. DOI: 10.1055/s-0035-1560534.
   Web of Science ®Google Scholar
• Farag, A. M.; Algharib, M. S. Synthesis and Reactions of C-(2-Thenoyl)-N-Arylformhydrazidoyl Bromides. Org. Prep. Proced. Int. 1988, 20, 521–526. DOI: 10.1080/00304948809356298.
   Web of Science ®Google Scholar
• Hosny, M.; Salem, M. E.; Darweesh, A. F.; Elwahy, A. H. M. Synthesis of Novel Bis(Thiazolylchromen-2-One) Derivatives Linked to Alkyl Spacer via Phenoxy Group. J. Heterocyclic Chem. 2018, 55, 2342–2348. DOI: 10.1002/jhet.3296.
   Web of Science ®Google Scholar
• Ibrahim, Y. A.; Elwahy, A. H. M.; Abbas, A. A. Salicylaldehyde Derivatives as Building Blocks in the Synthesis of Useful Open Chain and Macrocyclic Crown Compounds. J. Chem. Res. (S), 1998, 548–549. DOI: 10.1039/a802440e.
   Web of Science ®Google Scholar
• Ibrahim, Y. A.; Elwahy, A. H. M.; Elkareish, G. M. M. Synthesis of New Tetrabenzo Nitrogen-Oxygen Macrocycles Containing Two Amide Groups. J. Chem. Res. S 1994, 11, 414–415.
   Google Scholar
• Muathen, H. A.; Aloweiny, N. A. M.; Elwahy, A. H. M. Synthesis of Novel Amide-Crownophanes and Schiff Base-Crownophanes Based on p-Phenylene, 2,6-Naphthalene, and 9,10-Anthracene. J. Heterocyclic Chem. 2009, 46, 656–663. DOI: 10.1002/jhet.129.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Abbas, A. A. Synthesis of New Benzo-Substituted Macrocyclic Ligands Containing Pyridine or Triazole as Subcyclic Units. Tetrahedron 2000, 56, 885–895. DOI: 10.1016/S0040-4020(99)01068-6.
   Web of Science ®Google Scholar
• M. Abdella, A.; H. M. Elwahy, A.; A. Abdelhamid, I. Multicomponent Synthesis of Novel Bis(2-Amino-Tetrahydro-4H-Chromene-3- Carbonitrile) Derivatives Linked to Arene or Heteroarene Cores. Cos. 2016, 13, 601–610. DOI: 10.2174/1570179413999151211115100.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Masaret, G. S. Synthesis of Novel Benzo-Substituted Macrocyclic Schiff Bases Containing Two Triazole Rings. J. Heterocycl. Chem. 2007, 44, 1475–1484. DOI: 10.1002/jhet.5570440636.
   Web of Science ®Google Scholar
• Elwahy, A. H. M.; Darweesh, A. F.; Shaaban, M. R. Microwave-Assisted Synthesis of Bis(Enaminoketones): Versatile Precursors for Novel Bis(Pyrazoles) via Regioselective 1,3-Dipolar Cycloaddition with Nitrileimines. J. Heterocyclic Chem. 2012, 49, 1120–1125. DOI: 10.1002/jhet.952.
   Web of Science ®Google Scholar
• Elwahy, A. H. M. Difunctional Heterocycles: A Convenient Synthesis of Bis(4,5- Dihydropyrazolyl) Ethers from Their Precursor Bis(Chalcones). J. Chem. Res. (S), 1999, 602–603. DOI: 10.1039/a904716f.
   Web of Science ®Google Scholar
• Abdelhamid, I. A.; Darweesh, A. F.; Elwahy, A. H. M. Synthesis and Characterization of Poly(2,6-Dimethyl-4-Phenyl-1,4-Dihydropyridinyl)Arenes as Novel Multi-Armed Molecules. Tetrahedron Lett. 2015, 56, 7085–7088. DOI: 10.1016/j.tetlet.2015.11.015.
   Web of Science ®Google Scholar