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Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction

Year 2024, Volume: 7 Issue: 3, 80 - 89, 30.12.2024
https://doi.org/10.54994/emujpharmsci.1591288

Abstract

Microwave-assisted organic synthesis has gained significant attention for speeding up reactions, improving yields, and reducing reaction times. In this study, we investigated the microwave-induced reaction between dimedone and (1E,4E)-1,5-bis(4-fluorophenyl)penta-1,4-dien-3-one to synthesize 7,11-bis(4-fluorophenyl)-3,3-dimethylspiro[5.5]undecane-1,5,9-trione. The reaction was conducted using a microwave irradiation system, which allowed for a more environmentally friendly and energy-efficient process. Key parameters such as reaction time, temperature, and power settings were optimized for maximum yield. The synthesized compound was characterized using spectroscopic methods, including IR, ¹H-NMR, ¹³C-NMR, and mass spectrometry. The same reaction was also performed using a conventional method at room temperature which took 2-3 hours. The microwave approach was preferred due to its efficiency. Our findings indicate that microwave irradiation significantly enhances reaction efficiency, offering a fast method for synthesizing complex organic molecules. This technique has potential applications in various fields, including pharmaceutical chemistry and materials science, with a growing demand for sustainable and efficient chemical processes. Additionally, we conducted an in vitro anti-cancer activity experiment to evaluate the synthesized compound’s biological activity.

References

  • Ahmed MG, Ahmed SA, Romman U, Akhter K, Halim ME, et al. (2011). A one-pot synthesis of 7,11-diaryl-2,4-diazaspiro[5,5]undecane-3-oxo (or thioxo)-1,5,9-triones. Bangladesh Chem Soc 24: 135.
  • Ahmed MG, Romman UKR, Akhter K, Islam M, Hossain MM, et al. (2012). A Convenient Synthesis of Substituted Spiro[5.5] Undecanes Using Lewis Acid Catalysts. Dhaka Univ J Sci 60(1): 121-124.
  • Burgaz EV, Noshadi B, Yakut M (2024). Synthesis, Characterization, and Optimization of Novel Furan-ring Fused Chalcones via Radical Cyclization of α,β-Unsaturated Ketones and Cyclic Ketone. Lett Org Chem 21: 534.
  • Kunter I, Zabib N, Goger F, Kosar M (2023). New data for endemic Phlomis brevibracteata Turrill from North Cyprus: biological activities and chemical composition. Turk J Biochem 48: 475.
  • Majumdar P, Mohanta PP, Sahu S, Behera AK (2018). Studies on the synthesis of spiroheterocycles and their derivatives using dimedone as synthetic precursor. Synth Commun 48: 1747.
  • Okita T, Isobe M (1994). Palladium-catalyzed coupling of heteroaromatic triflates with acetylene and its application for a dynemicin a intermediate. Tetrahedron 50: 11143.
  • Puri S, Ahmad I, Patel H, Kumar K, Juvale K. (2023) Evaluation of oxindole derivatives as a potential anticancer agent against breast carcinoma cells: In vitro, in silico, and molecular docking study. Toxicol In Vitro 86:105517.
  • Soni JP, Chemitikanti KS, Joshi SV, Shankaraiah N (2020). The microwave-assisted syntheses and applications of non-fused single-nitrogen-containing heterocycles. Org Biomol Chem 18: 9737.
Year 2024, Volume: 7 Issue: 3, 80 - 89, 30.12.2024
https://doi.org/10.54994/emujpharmsci.1591288

Abstract

References

  • Ahmed MG, Ahmed SA, Romman U, Akhter K, Halim ME, et al. (2011). A one-pot synthesis of 7,11-diaryl-2,4-diazaspiro[5,5]undecane-3-oxo (or thioxo)-1,5,9-triones. Bangladesh Chem Soc 24: 135.
  • Ahmed MG, Romman UKR, Akhter K, Islam M, Hossain MM, et al. (2012). A Convenient Synthesis of Substituted Spiro[5.5] Undecanes Using Lewis Acid Catalysts. Dhaka Univ J Sci 60(1): 121-124.
  • Burgaz EV, Noshadi B, Yakut M (2024). Synthesis, Characterization, and Optimization of Novel Furan-ring Fused Chalcones via Radical Cyclization of α,β-Unsaturated Ketones and Cyclic Ketone. Lett Org Chem 21: 534.
  • Kunter I, Zabib N, Goger F, Kosar M (2023). New data for endemic Phlomis brevibracteata Turrill from North Cyprus: biological activities and chemical composition. Turk J Biochem 48: 475.
  • Majumdar P, Mohanta PP, Sahu S, Behera AK (2018). Studies on the synthesis of spiroheterocycles and their derivatives using dimedone as synthetic precursor. Synth Commun 48: 1747.
  • Okita T, Isobe M (1994). Palladium-catalyzed coupling of heteroaromatic triflates with acetylene and its application for a dynemicin a intermediate. Tetrahedron 50: 11143.
  • Puri S, Ahmad I, Patel H, Kumar K, Juvale K. (2023) Evaluation of oxindole derivatives as a potential anticancer agent against breast carcinoma cells: In vitro, in silico, and molecular docking study. Toxicol In Vitro 86:105517.
  • Soni JP, Chemitikanti KS, Joshi SV, Shankaraiah N (2020). The microwave-assisted syntheses and applications of non-fused single-nitrogen-containing heterocycles. Org Biomol Chem 18: 9737.
There are 8 citations in total.

Details

Primary Language English
Subjects Pharmaceutical Sciences
Journal Section Research Article
Authors

E. Vildan Burgaz

İmge Kunter 0000-0001-5706-306X

Publication Date December 30, 2024
Submission Date November 25, 2024
Acceptance Date December 25, 2024
Published in Issue Year 2024 Volume: 7 Issue: 3

Cite

APA Burgaz, E. V., & Kunter, İ. (2024). Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction. EMU Journal of Pharmaceutical Sciences, 7(3), 80-89. https://doi.org/10.54994/emujpharmsci.1591288
AMA Burgaz EV, Kunter İ. Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction. EMUJPharmSci. December 2024;7(3):80-89. doi:10.54994/emujpharmsci.1591288
Chicago Burgaz, E. Vildan, and İmge Kunter. “Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction”. EMU Journal of Pharmaceutical Sciences 7, no. 3 (December 2024): 80-89. https://doi.org/10.54994/emujpharmsci.1591288.
EndNote Burgaz EV, Kunter İ (December 1, 2024) Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction. EMU Journal of Pharmaceutical Sciences 7 3 80–89.
IEEE E. V. Burgaz and İ. Kunter, “Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction”, EMUJPharmSci, vol. 7, no. 3, pp. 80–89, 2024, doi: 10.54994/emujpharmsci.1591288.
ISNAD Burgaz, E. Vildan - Kunter, İmge. “Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction”. EMU Journal of Pharmaceutical Sciences 7/3 (December 2024), 80-89. https://doi.org/10.54994/emujpharmsci.1591288.
JAMA Burgaz EV, Kunter İ. Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction. EMUJPharmSci. 2024;7:80–89.
MLA Burgaz, E. Vildan and İmge Kunter. “Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction”. EMU Journal of Pharmaceutical Sciences, vol. 7, no. 3, 2024, pp. 80-89, doi:10.54994/emujpharmsci.1591288.
Vancouver Burgaz EV, Kunter İ. Synthesis and Anti-Cancer Activity of New Spiro[5.5]undecane Compound by Efficient Microwave Reaction. EMUJPharmSci. 2024;7(3):80-9.