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Research Article Open access CC BY 4.0

Synthesis, Biological Activity and Applications of 1,2,5-Oxadiazol: A Brief Review

João Rufino de Freitas Filho, Jucleiton José Rufino de Freitas, Juliano Carlo Rufino de Freitas, Clécio de Souza Ramos, Fabrícia Aparecida Marques de Souza, Jaqueline Ferreira Ramos, Ricarte Tavares, Drielly Emanoele Tomé Barros de Oliveira

International Research Journal of Pure and Applied Chemistry · pp. 1–26 · Published 5 Jan 2023

10.9734/irjpac/2023/v24i1798

Abstract

Oxadiazoles are heterocyclic compounds that belong azole class which contain two nitrogen atoms and one oxygen, forming a five-membered heterocyclic ring. Four isomers of oxadiazoles are described in the literature. Among these, 1,2,4-oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole have several applications biological. Compounds of this type have been used in the treatment of various diseases in both humans and animals.Among the immense class of heterocycle compounds with important biological activities already identified, the 1,2,5-oxadiazoles have stood out for the wide variety of applications in medicinal chemistry, in material, and agricultural chemistry. In this work, the main synthesis methods and advances for obtaining 1,2,5-oxadiazoles and their derivatives reported in the literature over the years are reviewed, as well as the applications of these compounds in several branches of chemistry and their biological activities discovered until the moment. GRAPHICAL ABSTRACT:

1,2,5-oxadiazoles biological activities medicinal chemistry NO donor

References (90)

  1. 1 Nitric Oxide Donors: Chemical Activities and Biological Applications [DOI]
  2. 2 The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications [DOI]
  3. 3 Blue light-emitting organic electroluminescent devices [DOI]
  4. 4 SUMO-Specific Protease 1 Is Essential for Stabilization of HIF1α during Hypoxia [DOI]
  5. 5 Identification of a novel mitochondrial uncoupler that does not depolarize the plasma membrane [DOI]
  6. 6 Role of Desumoylation in the Development of Prostate Cancer [DOI]
  7. 7 Combination of 1,2,4‐Oxadiazole and 1,2,5‐Oxadiazole Moieties for the Generation of High‐Performance Energetic Materials [DOI]
  8. 8 Advanced Synthetic Strategies for Constructing Quinazolinone Scaffolds [DOI]
  9. 9 SENP1 Induces Prostatic Intraepithelial Neoplasia through Multiple Mechanisms [DOI]
  10. 10 Synthesis and Biological Evaluation of Benzofuroxan Derivatives as Fungicides against Phytopathogenic Fungi [DOI]
  11. 11 Intramolecular 1,3-Dipolar Ene Reactions of Nitrile Oxides Occur by Stepwise 1,1-Cycloaddition/Retro-Ene Mechanisms [DOI]
  12. 12 EXPRESSION OF HUMAN PHASE II ENZYMES IN CHIMERIC MICE WITH HUMANIZED LIVER [DOI]
  13. 13 Dimerizations of Nitrile Oxides to Furoxans Are Stepwise via Dinitrosoalkene Diradicals: A Density Functional Theory Study [DOI]
  14. 14 Advances in the synthesis of non-annelated polynuclear heterocyclic systems comprising the 1,2,5-oxadiazole ring [DOI]
  15. 15 Nitrogen‐Rich Energetic 1,2,5‐Oxadiazole‐Tetrazole – Based Energetic Materials [DOI]
  16. 16 Identification of 1,2,5-Oxadiazoles as a New Class of SENP2 Inhibitors Using Structure Based Virtual Screening [DOI]
  17. 17 Benzofuroxan and Furoxan. Chemistry and Biology [DOI]
  18. 18 Fungal physiology – a future perspective [DOI]
  19. 19 Brønsted acid-promoted synthesis of common heterocycles and related bio-active and functional molecules [DOI]
  20. 20 Chimeric mice transplanted with human hepatocytes as a model for prediction of human drug metabolism and pharmacokinetics [DOI]
  21. 21 1, 2, 4-Oxadiazoles [DOI]
  22. 22 Mutation of SENP1/SuPr-2 Reveals an Essential Role for Desumoylation in Mouse Development [DOI]
  23. 23 Furazan*,1,2 [DOI]
  24. 24 Electronic and Vibrational Polarizabilities and Hyperpolarizabilities of Azoles: A Comparative Study of the Structure−Polarization Relationship [DOI]
  25. 25 1,2,5-Oxadiazole N-oxide derivatives as potential anti-cancer agents: synthesis and biological evaluation. Part IV [DOI]
  26. 26 Synthesis and biological evaluation of 3,4-diphenyl-1,2,5-oxadiazole-2-oxides and 3,4-diphenyl-1,2,5-oxadiazoles as potential hybrid COX-2 inhibitor/nitric oxide donor agents [DOI]
  27. 27 Synthesis and Herbicidal Activity of N-Oxide Derivatives [DOI]
  28. 28 Benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as potential antitrypanosomal drugs. Part 3: Substituents-clustering methodology in the search for new active compounds [DOI]
  29. 29 Synthesis and antimalarial activities of some furoxan sulfones and related furazans [DOI]
  30. 30 Transition metal-free one-pot synthesis of nitrogen-containing heterocycles [DOI]
  31. 31 Alumina promoted cyclization of α-nitro-oximes: a new entry to the synthesis of 1,2,5-oxadiazoles N-oxides (furoxans) [DOI]
  32. 32 Use of the furoxan (1,2,5-oxadiazole 2-oxide) system in the design of new NO-donor antioxidant hybrids [DOI]
  33. 33 Studies in 3,4-diaryl-1,2,5-oxadiazoles and their N-oxides: Search for better COX-2 inhibitors [DOI]
  34. 34 Utilization of wieland furoxan synthesis for preparation of 4-aryl-1,2,5-oxadiazole-3-yl carbamate derivatives having potent anti-HIV activity [DOI]
  35. 35 Cytotoxicity of furoxans: quantitative structure-activity relationships study [DOI]
  36. 36 One-pot access to a privileged library of six membered nitrogenous heterocycles through multi-component cascade approach [DOI]
  37. 37 Preparation of 4,7-Dihetaryl-1,2,5-oxadiazolo[3,4-c]pyridines as Red Fluorescent Materials [DOI]
  38. 38 New and Emerging Treatments for Cystic Fibrosis [DOI]
  39. 39 Reaction of Oximes of α-Diketones with Diphosphorous Tetraiodide for Preparation of Oxadiazoles and Nitriles [DOI]
  40. 40 Relationship Between Physicochemical Properties and Herbicidal Activity of 1,2,5-Oxadiazole N-Oxide Derivatives [DOI]
  41. 41 Benzofuroxan (Benzo[1,2-c]1,2,5-oxadiazole N-oxide) Derivatives as Potential Energetic Materials: Studies on Their Synthesis and Properties
  42. 42 Ring-opening and recyclization of 3,4-diacylfuroxans by nitrogen nucleophiles [DOI]
  43. 43 Furo[3,4-b]benzofurans: synthesis and reactions [DOI]
  44. 44 Safety vs Efficiency in the Development of a High-Energy Compound [DOI]
  45. 45 Fungicidal and toxicological properties of functionally substituted nitrobenzofuroxanes [DOI]
  46. 46 New phenanthrene systems: spiro-fused tricyclic phenanthro-1,2,4-triazolo-[4,3-d]-1,2,4-triazines and -[3,4-d]-1,2,5-oxadiazines: ring expansions of N-methylphenanthroazoliums [DOI]
  47. 47 On the Interaction of 3,4-Dibenzoylfuroxan with Hydroxylamine [DOI]
  48. 48 One-pot synthesis of some (1H)-quinoxalin-2-ones [DOI]
  49. 49 Fluorescence spectroscopic characterization of 4,7-bis(2-thienyl)-1,2,5-oxadiazolo[3,4-c]pyridine; lead structure of new red-emitting EL material [DOI]
  50. 50 HIV resistance to raltegravir [DOI]
  51. 51 Modern advances in heterocyclic chemistry in drug discovery [DOI]
  52. 52 The Modern Face of Synthetic Heterocyclic Chemistry [DOI]
  53. 53 Anti-Cancer Activity of Derivatives of 1,3,4-Oxadiazole [DOI]
  54. 54 Isocyanide-based multicomponent reactions in the synthesis of heterocycles [DOI]
  55. 55 1,2,5‐Oxadiazole‐Based High‐Energy‐Density Materials: Synthesis and Performance [DOI]
  56. 56 1,3,4-Oxadiazoles as luminescent materials for organic light emitting diodes via cross-coupling reactions [DOI]
  57. 57 1,2,4- and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents [DOI]
  58. 58 Asymmetric Hydrogenation of Heteroarenes with Multiple Heteroatoms [DOI]
  59. 59 Recent advances in the synthesis and functionalization of 1,2,5-oxadiazole 2-oxides [DOI]
  60. 60 Opportunities and challenges for direct C–H functionalization of piperazines [DOI]
  61. 61 [1,2,5]Oxadiazolo[3,4-b]pyrazine-5,6-diamine Derivatives as Mitochondrial Uncouplers for the Potential Treatment of Nonalcoholic Steatohepatitis [DOI]
  62. 62 A Novel Parkinson’s Disease Drug Candidate with Potent Anti-neuroinflammatory Effects through the Src Signaling Pathway [DOI]
  63. 63 Design, synthesis, and biological evaluation of 1,2,5-oxadiazole-3-carboximidamide derivatives as novel indoleamine-2,3-dioxygenase 1 inhibitors [DOI]
  64. 64 Finding furoxan rings [DOI]
  65. 65 Boosting the Energetic Performance of Trinitromethyl-1,2,4-oxadiazole Moiety by Increasing Nitrogen-Oxygen in the Bridge [DOI]
  66. 66 A Family of Energetic Materials Based on 1,2,4-Oxadiazole and 1,2,5-Oxadiazole Backbones With Low Insensitivity and Good Detonation Performance [DOI]
  67. 67 Novel benzo[c][1,2,5]oxadiazole-naphthalenediimide based copolymer for high-performance air-stable n-type field-effect transistors exhibiting high electron mobility of 2.43 cm 2 V −1 s −1 [DOI]
  68. 68 Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii [DOI]
  69. 69 Synthesis and Antitumor Evaluation of Novel Hybrids of Phenylsulfonylfuroxan and Estradiol Derivatives [DOI]
  70. 70 Synthesis of Nitro, Dinitro, and Polynitroalkylamino Derivatives of Trifurazanoxide [DOI]
  71. 71 Discovery of Hydroxyamidine Based Inhibitors of IDO1 for Cancer Immunotherapy with Reduced Potential for Glucuronidation [DOI]
  72. 72 Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study [DOI]
  73. 73 Characterization of water-soluble esters of nitrobenzoxadiazole-based GSTP1-1 inhibitors for cancer treatment [DOI]
  74. 74 Furoxan derivatives as cytotoxic agents: preliminary in vivo antitumoral activity studies.
  75. 75 Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent [DOI]
  76. 76 Renaissance of 1,2,5‐Oxadiazolyl Diazonium Salts: Synthesis and Reactivity [DOI]
  77. 77 Efficient preparation and comprehensive properties of thermal decomposition and detonation for 4,4′-dinitro-3,3′-azofuroxan [DOI]
  78. 78 Energetic Compounds Based on 3,4‐Bis(4‐nitramino‐ 1,2,5‐oxadiazol‐3‐yl)‐1,2,5‐furoxan (BNAFF) [DOI]
  79. 79 One-pot synthesis of 3-amino-4-aryl- and 3-amino-4-hetarylfurazans [DOI]
  80. 80 3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] [DOI]
  81. 81 Novel Energetic Compounds Based on 3-Methyl-1,2,5-Oxadiazole 2-Oxide [DOI]
  82. 82 Formation and Characterization of Heavy Alkali and Silver Salts of the 4‐Nitro‐pyrazolo‐(3,4‐c)‐furazan‐5‐N‐oxide Anion [DOI]
  83. 83 Complex formation of copper( ii ), nickel( ii ) and zinc( ii ) with ethylophosphonoacetohydroxamic acid: solution speciation, synthesis and structural characterization [DOI]
  84. 84 Nitramino-furazan-functionalized fused high-nitrogen backbones as energetic materials with high detonation performance and good molecular stabilities [DOI]
  85. 85 Catalytic Asymmetric Syntheses of Indenes and Their Derivatives [DOI]
  86. 86 An expedient synthesis of new 2-(furoxan-3-yl)thiazolidin-4-one derivatives [DOI]
  87. 87 Synthesis of monothiooxamides of the thiazole series [DOI]
  88. 88 Synthesis of Oxadiazole Derivative of Pentacyclic Triterpenoid and Its Biological Activity [DOI]
  89. 89 Crystal structure of poly[(μ3-4-amino-1,2,5-oxadiazole-3-hydroxamato)thallium(I)] [DOI]
  90. 90 Comprehensive Heterocyclic Chemistry [DOI]

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