Use of NMR and Other Spectroscopy Techniques in Heterocyclic Oxadiazole Derivatives Studies: A Review

Year : 2025 | Volume : 02 | Issue : 01 | Page : 07 13
    By

    Neha Sahu,

  1. Research Scholar, Department of Chemistry School of Basic and Applied Sciences, Lingaya’s Vidyapeeth, Haryana, India

Abstract

It was possible to create a number of novel symmetrical 2,5-dialkyl-1,3,4-oxadiazoles with substituents including carboxymethylamino, isopropyloxycarbonylmethylamino, and bromine at the terminal positions of the alkyl groups. The multistep process that was devised used hydrazine hydrate, phosphorus oxychloride, and commercially available acid chlorides that varied in alkyl chain length and terminal substituent.Diisopropyliminodiacetate was an easy way to substitute the intermediate bromine-containing 2,5-dialkyl-1,3,4-oxadiazoles. This was followed by hydrolysis in an aqueous methanol solution, which produced the corresponding 1,3,4-oxadiazoles with carboxymethylamino substituents. All of the products’ structures were verified using standard spectroscopic techniques such 1H NMR, 13C NMR, and HRMS. One of the most significant heterocyclic fragments and a potential building block for drug discovery is the 1,3,4-oxadiazole scaffold. Substituted 1,3,4-oxadiazoles exhibit a wide range of pharmacological properties, including antitubercular, anticancer, anti-inflammatory, antibacterial, antiviral, antifungal, insecticidal, antioxidant, and analgesic effects. Additionally, licensed medications such as the antiviral drug Raltegravir, the anticancer drug Zibotentan, and the antihypertensive drugs Tiodazosin and Nesapidil contain the 1,3,4-oxadiazole core. This review compiles the primary methods for determining potential avenues for structural modification and pharmacological activity of non- condensed heterocyclic systems based on the 1,3,4-oxadiazole ring, highlighting their promise as targets in contemporary bioorganic and medicinal chemistry.

Keywords: 1,3,4-oxadiazoles; organic ligands; heterocycles; substitution; spectral characterization

[This article belongs to International Journal of Photochemistry and Photochemical Research ]

How to cite this article:
Neha Sahu. Use of NMR and Other Spectroscopy Techniques in Heterocyclic Oxadiazole Derivatives Studies: A Review. International Journal of Photochemistry and Photochemical Research. 2024; 02(01):07-13.
How to cite this URL:
Neha Sahu. Use of NMR and Other Spectroscopy Techniques in Heterocyclic Oxadiazole Derivatives Studies: A Review. International Journal of Photochemistry and Photochemical Research. 2024; 02(01):07-13. Available from: https://journals.stmjournals.com/ijppr/article=2024/view=208595


References

  1. Abbasi MA, Hassan M, Aziz-ur-Rehman, Siddiqui SZ, Raza H, Shah SAA, Seo S-Y. Synthesis, in vitro and in silico studies of novel potent urease inhibitors: N-[4-({5-[(3-Un/substituted-anilino-3-oxopropyl)-sulfanyl]-1,3,4-oxadiazol-2-yl}methyl)-1,3-thiazol-2-yl]benzamides. Bioorganic & Medicinal Chemistry, 2018; 26: 3791–3804.
  2. Ahsan JA, Choupra A, Sharma RK, Jadav SS, Padmaja P, Hassan MZ, Al-Tamimi ABS, Geesi MH, Bakht MA. Rational design, synthesis, cytotoxicity evaluation, and molecular docking studies of 1,3,4-oxadiazole analogues. Anti-Cancer Agents in Medicinal Chemistry, 2018; 18: 121–138.
  3. Lelyukh M, Martynets M, Kalytovska M, Drapak I, Harkov S, Chaban T, Matiychuk V. Approaches for synthesis and chemical modification of non-condensed heterocyclic systems based on 1,3,4-oxadiazole ring and their biological activity: A review. Journal of Applied Pharmaceutical Science, 2020; 10: 151–165. doi:10.7324/JAPS.2020.1010016.
  4. Luczynski M, Kudelko A. Synthesis and biological activity of 1,3,4-oxadiazoles used in medicine and agriculture. Applied Sciences, 2022; 12: 3756. doi:10.3390/app12083756.
  5. Huang M, Li L, Xie W, Yan N, Yuan L, Zhu Z, Jiang Z. Fabrication and characterization of modified POD membranes with ultra-high tensile strength through hydrogen bonding functioning and copolymerization. High Performance Polymers, 2024; 36(2): 71–81.
  6. Tejeswara Rao A, Jaya Shree A. Novel 7-substituted fluoroquinolone citrate conjugates as powerful antibacterial and anticancer agents: synthesis and molecular docking studies. Current Organic Chemistry, 2019; 23: 1991–2002.
  7. Arora R, Issar U, Kakkar R. In silico study of the active site of Helicobacter pylori urease and its inhibition by hydroxamic acids. Journal of Molecular Graphics and Modelling, 2018; 83: 64–73.
  8. Abbas AA, Dawood KM. Anticancer therapeutic potential of benzofuran scaffolds. RSC Advances, 2023; 13(16): 11096–11120.
  9. Diana R, Caruso U, Di Costanzo L, Bakayoko G, Panunzi B. A novel DR/NIR T-shaped AIEgen: synthesis and X-ray crystal structure study. Crystals, 2020; 10(4).
  10. Diana R, Caruso U, Gentile FS, Di Costanzo L, Panunzi B. A novel L-shaped fluorescent probe for AIE sensing of zinc(II) ion by a DR/NIR response. Molecules, 2021; 26(23).
  11. Diana R, Caruso U, Gentile FS, Di Costanzo L, Turrà D, Vitale S, et al. Benzodifuran-based fluorescent brighteners: a novel platform for plant cell wall imaging. Dyes and Pigments, 2022; 199.
  12. Diana R, Gentile FS, Concilio S, Petrella A, Belvedere R, Schibeci M, et al. A DR/NIR hybrid polymeric tool for functional bio-coatings: theoretical study, cytotoxicity, and antimicrobial activity. Polymers, 2023; 15(4): 883.
  13. Sarkar A, Sessa L, Marrafino F, Piotto S. GUIDE: a GUI for automated quantum chemistry calculations. Journal of Computational Chemistry, 2023; 44(25): 2030–2036.
  14. JamorskiJödicke C, Lüthi HP. Time-dependent density functional theory (TDDFT) study of the excited charge-transfer state formation of a series of aromatic D–A systems. Journal of the American Chemical Society, 2003; 125(1): 252–264.
  15. Diana R, Panunzi B. Zinc(II) and AIEgens: the “i-a-a” for a novel fluorophore family – a review. Molecules, 2021; 26(14).
  16. Li L, Sun H. Next generation of small-molecule fluorogenic probes for bioimaging. Biochemistry, 2020; 59(3): 216–217.
  17. Wan Q, Tong J, Zhang B, Li Y, Wang Z, Tang BZ. Exploration of high-efficiency AIE-active deep/near-infrared red emitters in OLEDs with high radiance. Advanced Optical Materials, 2020; 8(4): 1901520.
  18. Liu J, Geng Y, Li D, Yao H, Huo Z, Li Y, et al. Deep red emissive carbonized polymer dots with unprecedented narrow full width at half maximum. Advanced Materials, 2020; 32(17): 1906641.
  19. Szlasa W, Gachowska M, Kiszka K, Rakoczy K, Kiliś A, Wala K, et al. Iron chelates in anticancer therapy. Chemical Papers, 2022; 76(3): 1285–1294.
  20. Abbas AM, Aboelmagd A, Kishk SM, Nasrallah HH, Boyd WC, Kalil H, et al. A novel ibuprofen derivative and its complexes: physicochemical characterization, DFT modeling, docking, in vitro anti-inflammatory studies, and DNA interaction. Molecules, 2022; 27(21).
Regular Issue Subscription Review Article
Volume 02
Issue 01
Received 05/07/2024
Accepted 24/07/2024
Published 28/07/2024
Publication Time 23 Days
324

Login


My IP

PlumX Metrics