Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties

Catalin V. Maftei, Elena Fodor, Peter G. Jones, M. Heiko Franz, Gerhard Kelter, Heiner Fiebig and Ion Neda
Beilstein J. Org. Chem. 2013, 9, 2202–2215. https://doi.org/10.3762/bjoc.9.259

Cite the Following Article

Synthesis and characterization of novel bioactive 1,2,4-oxadiazole natural product analogs bearing the N-phenylmaleimide and N-phenylsuccinimide moieties
Catalin V. Maftei, Elena Fodor, Peter G. Jones, M. Heiko Franz, Gerhard Kelter, Heiner Fiebig and Ion Neda
Beilstein J. Org. Chem. 2013, 9, 2202–2215. https://doi.org/10.3762/bjoc.9.259

How to Cite

Maftei, C. V.; Fodor, E.; Jones, P. G.; Franz, M. H.; Kelter, G.; Fiebig, H.; Neda, I. Beilstein J. Org. Chem. 2013, 9, 2202–2215. doi:10.3762/bjoc.9.259

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Singh, S.; Lakhia, R.; Yadav, S.; Devi, P.; Yadav, K.; Chaudhri, V.; Pundeer, R. Advancements in the Synthesis of Triazolopyrimidines. Current Organic Chemistry 2024, 28, 1567–1578. doi:10.2174/0113852728313437240607095009
  • Nair, V. A.; Radhakrishna, V. Y.; Khatik, G. L. 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxide to Thiocyanates: An Efficient and Eco-Friendly Synthesis of N-Aryl-2-((3-aryl-1,2,4-oxadiazol-5-yl)thio)acetamides. Synthesis 2024, 56, 3173–3180. doi:10.1055/s-0043-1775390
  • Kucukoglu, K.; Faydali, N.; Bul, D.; Nadaroglu, H.; Sever, B.; Altıntop, M. D.; Ozturk, B.; Guzel, I. Synthesis, in silico and in vitro evaluation of new 3,5-disubstituted-1,2,4-oxadiazole derivatives as carbonic anhydrase inhibitors and cytotoxic agents. Journal of Molecular Structure 2023, 1276, 134699. doi:10.1016/j.molstruc.2022.134699
  • Chilaka, S. K.; Chellu, R. K.; Soda, A. K.; Kurva, S.; Nanubolu, J. B.; Madabhushi, S. Base‐Catalyzed Domino Reaction Between Aldoxime and N‐Chlorosuccinimide in Alcohol: One‐Pot Synthesis of Alkyl 3‐(3‐Aryl‐1,2,4‐oxadiazol‐5‐yl)propanoates. Advanced Synthesis & Catalysis 2022, 364, 2944–2950. doi:10.1002/adsc.202200265
  • Desai, K. R.; Patel, B. R. Various Synthetic Strategies and Therapeutic Potential of Thiadiazole, Oxadiazole, Isoxazole and Isothiazole Derivatives. N-Heterocycles; Springer Nature Singapore, 2022; pp 221–274. doi:10.1007/978-981-19-0832-3_6
  • Zhang, C. Application of Aromatic Substituted 2,2,2-Trifluoro Diazoethanes in Organic Reactions. Current Organic Chemistry 2022, 26, 639–650. doi:10.2174/1385272826666220516113815
  • Roy, J. The synthesis and applications of TiO2 nanoparticles derived from phytochemical sources. Journal of Industrial and Engineering Chemistry 2022, 106, 1–19. doi:10.1016/j.jiec.2021.10.024
  • Wolf, L.; Mayer, J. C.; Quoos, N.; Sauer, A. C.; Schwab, R. S.; Rodrigues, O. E. D.; Dornelles, L. One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation. Tetrahedron 2021, 91, 132222. doi:10.1016/j.tet.2021.132222
  • Farooq, M. U.; Naz, M. Y.; Hussain, M.; Shukrullah, S.; Makhlouf, M. M. Smart Therapeutic Strategy of pH-Responsive Gold Nanoparticles for Combating Multidrug Resistance. Particle & Particle Systems Characterization 2021, 38, 2100073. doi:10.1002/ppsc.202100073
  • Kapoor, G.; Bhutani, R.; Pathak, D. P.; Chauhan, G.; Kant, R.; Grover, P.; Nagarajan, K.; Siddiqui, S. A. Current Advancement in the Oxadiazole-Based Scaffolds as Anticancer Agents. Polycyclic Aromatic Compounds 2021, 1–33.
  • Kapoor, G.; Bhutani, R.; Pathak, D. P.; Chauhan, G.; Kant, R.; Grover, P.; Nagarajan, K.; Siddiqui, S. A. Current Advancement in the Oxadiazole-Based Scaffolds as Anticancer Agents. Polycyclic Aromatic Compounds 2021, 42, 4183–4215. doi:10.1080/10406638.2021.1886123
  • Avila, C.; Angulo-Preckler, C. Bioactive Compounds from Marine Heterobranchs. Marine drugs 2020, 18, 657. doi:10.3390/md18120657
  • Woliński, P.; Kącka-Zych, A.; Demchuk, O. M.; Łapczuk-Krygier, A.; Miroslaw, B.; Jasiński, R. Clean and molecularly programmable protocol for preparation of bis-heterobiarylic systems via a domino pseudocyclic reaction as a valuable alternative for TM-catalyzed cross-couplings. Journal of Cleaner Production 2020, 275, 122086. doi:10.1016/j.jclepro.2020.122086
  • Baikov, S. V.; Trukhanova, Y. A.; Tarasenko, M. V.; Kinzhalov, M. A. Synthesis and Study of the Structure of Palladium(II) AcyclicDiaminocarbene Complexes Containing a 1,2,4-Oxadiazole Moiety. Russian Journal of General Chemistry 2020, 90, 1892–1900. doi:10.1134/s1070363220100126
  • Penjarla, S.; Sabui, S. K.; Reddy, D. S.; Banerjee, S.; Reddy, P. Y.; Penta, S.; Sanghvi, Y. S. An efficient synthesis tetrazole and oxadiazole analogues of novel 2′-deoxy-C-nucleosides and their antitumor activity. Bioorganic & medicinal chemistry letters 2020, 30, 127612. doi:10.1016/j.bmcl.2020.127612
  • Ceramella, J.; Mariconda, A.; Rosano, C.; Iacopetta, D.; Caruso, A.; Longo, P.; Sinicropi, M. S.; Saturnino, C. α-ω Alkenyl-bis-S-Guanidine Thiourea Dihydrobromide Affects HeLa Cell Growth Hampering Tubulin Polymerization. ChemMedChem 2020, 15, 2306–2316. doi:10.1002/cmdc.202000544
  • Biernacki, K.; Daśko, M.; Ciupak, O.; Kubiński, K.; Rachon, J.; Demkowicz, S. Novel 1,2,4-Oxadiazole Derivatives in Drug Discovery. Pharmaceuticals (Basel, Switzerland) 2020, 13, 111. doi:10.3390/ph13060111
  • Özer, B.; Dürüst, Y. Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties. Russian Journal of Organic Chemistry 2020, 56, 698–705. doi:10.1134/s1070428020040193
  • El-Mekabaty, A.; Etman, H. A.; Mosbah, A.; Fadda, A. A. Synthesis, In Vitro Cytotoxicity and Bleomycin-Dependent DNA Damage Evaluation of Some Heterocyclic-Fused Pyrimidinone Derivatives. ChemistrySelect 2020, 5, 4856–4861. doi:10.1002/slct.202001006
  • Bumbăcilă, B.; Putz, M. V. Neurotoxicity of Pesticides: The Roadmap for the Cubic Mode of Action. Current medicinal chemistry 2020, 27, 54–77. doi:10.2174/0929867326666190704142354

Patents

  • GUO YUEWEI; ZHANG HAIYAN; XIAO WEI; WANG ZHENZHONG; JIANG CHENGSHI; FU YAN. Indole alkaloids possessing 1,2,4-oxadiazole fragment, and preparation method and application thereof. CN 105272975 A, Jan 27, 2016.
Other Beilstein-Institut Open Science Activities