Research Article
BibTex RIS Cite

Rational Design, Synthesis, and Comprehensive Characterization of Novel 1,4-Pentadien-3-one Derivatives Bearing Oxime Moieties

Year 2025, Volume: 12 Issue: 4, 235 - 240
https://doi.org/10.18596/jotcsa.1734865

Abstract

The purpose of this research is to synthesize a series of novel 1,4-pentadien-3-one oximes and 1,4-pentadien-3-one O-benzoyl oximes. In this work, new 1,4-pentadien-3-one derivatives with oxime moieties are logically designed, synthesized, and thoroughly characterized. Using a multi-step synthetic strategy, a number of 1,4-pentadien-3-one derivatives were created by functionalizing the core structure with oxime functionalities. The structures of the newly synthesized compounds were determined by several spectroscopic methods, including Nuclear Magnetic Resonance Spectroscopy (1H NMR, 13C NMR) and Mass Spectroscopy.

References

  • 1. Adams BK, Ferstl EM, Davis MC, Herold M, Kurtkaya S, Camalier RF, et al. Synthesis and biological evaluation of novel curcumin analogs as anti-cancer and anti-angiogenesis agents. Bioorg Med Chem [Internet]. 2004 Jul;12(14):3871–83. Available from: <URL>.
  • 2. Priyadarsini K. The chemistry of curcumin: From extraction to therapeutic agent. Molecules [Internet]. 2014 Dec 1;19(12):20091–112. Available from: <URL>.
  • 3. Weber WM, Hunsaker LA, Abcouwer SF, Deck LM, Vander Jagt DL. Anti-oxidant activities of curcumin and related enones. Bioorg Med Chem [Internet]. 2005 Jun;13(11):3811–20. Available from: <URL>.
  • 4. Martín Ortega AM, Segura Campos MR. Medicinal plants and their bioactive metabolites in cancer prevention and treatment. In: Bioactive Compounds [Internet]. Elsevier; 2019. p. 85–109. Available from: <URL>.
  • 5. El-Kenawy AEM, Hassan SMA, Mohamed AMM, Mohammed HMA. Tumeric or Curcuma longa Linn. In: Nonvitamin and Nonmineral Nutritional Supplements [Internet]. Elsevier; 2019. p. 447–53. Available from: <URL>.
  • 6. Pandey P, Awasthi R, Dhiman N, Sharma B, Kulkarni GT. Ethnopharmacological reports on herbs used in the management of tuberculosis. In: Herbal Medicines [Internet]. Elsevier; 2022. p. 501–23. Available from: <URL>.
  • 7. Dasgupta A. Antiinflammatory herbal supplements. In: Translational Inflammation [Internet]. Elsevier; 2019. p. 69–91. Available from: <URL>.
  • 8. Malik D e shahwar, Pimentel TC, Mahmood NN, Farooqi AA. Antimetastatic effects of curcumin. In: Unraveling the Complexities of Metastasis [Internet]. Elsevier; 2022. p. 249–58. Available from: <URL>.
  • 9. Francieli da Silva G, Rocha LW, Quintão NLM. Nutraceuticals, dietary supplements, and functional foods as alternatives for the relief of neuropathic pain. In: Bioactive Nutraceuticals and Dietary Supplements in Neurological and Brain Disease [Internet]. Elsevier; 2015. p. 87–93. Available from: <URL>.
  • 10. Huang MT, Lysz thomas, Ferrano T, Abidi TF, Laskin JD, Conney AH. Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Cancer Res [Internet]. 1993;51(3):813–9. Available from: <URL>.
  • 11. Noureddin SA, El-Shishtawy RM, Al-Footy KO. Curcumin analogues and their hybrid molecules as multifunctional drugs. Eur J Med Chem [Internet]. 2019 Nov 15;182:111631. Available from: <URL>.
  • 12. Omidi S, Kakanejadifard A. A review on biological activities of schiff base, hydrazone, and oxime derivatives of curcumin. RSC Adv [Internet]. 2020 Aug 17;10(50):30186–202. Available from: <URL>.
  • 13. Li SB, Song BA, Yang S, Jin LH, Xue W, Zeng S, et al. Synthesis and antifungal activity of novel 1,5-diphenyl- 1,4-pentadien-3-one oxime esters. Chinese J Org Chem [Internet]. 2008;28:311–6. Available from: <URL>.
  • 14. Erdoğan T. The first synthesis of some novel 4-chloro chalcone based oxime Ethers: An experimental and computational study. SDÜ Fen Bilim Enstitüsü Derg [Internet]. 2016 Nov 24;20(3):475–89. Available from: <URL>.
  • 15. Rayar A, Veitía MSI, Ferroud C. An efficient and selective microwave-assisted Claisen-Schmidt reaction for the synthesis of functionalized benzalacetones. Springerplus [Internet]. 2015 Dec 14;4(1):221. Available from: <URL>.
  • 16. Erdogan T. Synthesis, characterization, DFT and molecular docking studies for novel 1,5-diphenylpenta-1,4-dien-3-one O-benzyl oximes. J Iran Chem Soc [Internet]. 2019 Oct 24;16(10):2243–55. Available from: <URL>.
  • 17. Attia M, Zakaria A, Almutairi M, Ghoneim S. In Vitro anti-candida activity of certain new 3-(1H-Imidazol-1-yl)propan-1-one oxime esters. Molecules [Internet]. 2013 Sep 30;18(10):12208–21. Available from: <URL>.
  • 18. Burgaz EV, Noshadi B, Yakut M. Synthesis, characterization, and optimization of novel furan-ring fused chalcones via radical cyclization of α,β-unsaturated ketones and cyclic ketone. Lett Org Chem [Internet]. 2024 Jun;21(6):534–40. Available from: <URL>.
  • 19. Tang X, Su S, Li Q, He J, Chen M, Chen Y, et al. Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives. J Pestic Sci [Internet]. 2019 Nov 20;44(4):242–8. Available from: <URL>.
  • 20. Chen L, Wang X, Tang X, Xia R, Guo T, Zhang C, et al. Design, synthesis, antiviral bioactivities and interaction mechanisms of penta-1,4-diene-3-one oxime ether derivatives containing a quinazolin-4(3H)-one scaffold. BMC Chem [Internet]. 2019 Dec 25;13(1):34. Available from: <URL>.
  • 21. Li JT, Zhai XL, Bai B, Liang YH. An efficient synthesis of 1,5-Diaryl-1,4-pentadien-3-one oxime in the presence of anhydrous sodium sulfate. Lett Org Chem [Internet]. 2010 Jun 1;7(4):323–6. Available from: <URL>.
  • 22. Nasir Abbas Bukhari S, Jasamai M, Jantan I, Ahmad W. Review of Methods and Various Catalysts Used for Chalcone Synthesis. Mini Rev Org Chem [Internet]. 2013 Mar 1;10(1):73–83. Available from: <URL>.
  • 23. Burgaz EV, Yakut M, Kunter İ. Efficient microwave synthesis and anti-cancer evaluation of new substituted 2,4-diazaspiro[5.5]undecane-1,5,9-trione (or 1,3,5,9-tetraone) derivatives. Joule JA, editor. Arkivoc [Internet]. 2024 Dec 9;2024(8). Available from: <URL>.
  • 24. Su S, Chen M, Li Q, Wang Y, Chen S, Sun N, et al. Novel penta-1,4-diene-3-one derivatives containing quinazoline and oxime ether fragments: Design, synthesis and bioactivity. Bioorg Med Chem [Internet]. 2021 Feb;32:115999. Available from: <URL>.
  • 25. Ferreira LOA, Valdo AKSM, Nascimento Neto JA, Ribeiro L, Silva JRD da, Queiroz LHK, et al. ss-NMR and single-crystal X-ray diffraction in the elucidation of a new polymorph of bischalcone (1 E ,4 E )-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one. Acta Crystallogr Sect C Struct Chem [Internet]. 2019 Jun 1;75(6):694–701. Available from: <URL>.
  • 26. Naik N, Kumar HV, Swetha S. 1,5-diphenylpenta-1,4 dien-3-ones: A novel class of free radical scavengers. Bulg Chem Commun [Internet]. 2011;43(3):460–4. Available from: <URL>.
There are 26 citations in total.

Details

Primary Language English
Subjects Organic Chemical Synthesis
Journal Section RESEARCH ARTICLES
Authors

E. Vildan Burgaz 0000-0003-3245-5934

Mahya Tanha 0000-0001-5822-5366

Seyed Armin Houshmand Kia 0000-0002-4468-8703

Publication Date November 17, 2025
Submission Date July 5, 2025
Acceptance Date October 5, 2025
Published in Issue Year 2025 Volume: 12 Issue: 4

Cite

Vancouver Burgaz EV, Tanha M, Houshmand Kia SA. Rational Design, Synthesis, and Comprehensive Characterization of Novel 1,4-Pentadien-3-one Derivatives Bearing Oxime Moieties. JOTCSA. 12(4):235-40.