The Synthesis and Spectral Properties of Benzofuran Derivative bis-Chalcone

  • Neslihan Beyazit Mustafa Kemal University, Department of Chemistry, Faculty of Arts and Sciences, Hatay, Turkey http://orcid.org/0000-0002-5722-2400

Abstract

Khellin, a natural furanochromone, was isolated from the fruits of Ammi visnaga L. by using a rapid and easy technique. It was then hydrolyzed with 10% KOH to obtain khellinone. From the Claisen-Schmidt condensation of khellinone with terephthalaldehyde, a new benzofuran derivative bis-chalcone was synthesized and its spectroscopic properties were investigated in details.

Keywords:

Khellin; Khellinone; Ammi visnaga L.; Claisen Schmidt condensation; Bis-chalcone

DOI: 10.17350/HJSE19030000067

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References

1. Xue Y, LiuY, An L, Zhang, L, Yuan Y, Mou, J, Liu L, Zheng Y. Electronic structures and spectra of quinoline chalcones: DFT and TDDFT-PCM investigation. Computational and Theoretical Chemistry 965 (2011) 146–153. https://doi.org/10.1016/j.comptc.2011.01.042.2. Gammill RB. The Synthesis and Chemistry of Functionalized Furochromones.

2. The Synthesis, Sommelet-Hauser Rearrangement, and Conversion of 4,9-Dimethoxy-7-[(methylthio)methyl]-5H-furo[3,2-g][1]benzopyran-5-one to Ammiol. Journal of Organic Chemistry 49 (1984) 5035-5041. DOI:10.1021/jo00200a002.

3. Osman SA, Yosef HAA, Hafez TS, El-Sawy AA, Mousa HA, Hassan AS. Synthesis and Antibacterial Activity of Some Novel Chalcones, Pyrazoline and 3- Cyanopyridine Derivatives Based on Khellinone as well as Ni(II), Co(II) and Zn(II) Complexes. Australian Journal of Basic and Applied Sciences. 6 (2012) 852-863.

4. Baell JB, Gable RW, Harvey AJ, Toovey N, Herzog T, Hansel W, Wulff H. Khellinone Derivatives as Blockers of the Voltage-Gated Potassium Channel Kv1.3: Synthesis and Immunosuppressive Activity. Journal of Medicinal Chemistry 47 (2004) 2326-2336. DOI:10.1021/jm030523s.

5. Ahmed Farag IS, Abd El-Hafez OM, Rybakov VB. Crystal Structure of a New Chalcone Compound Prepared from Khellinone. Crystal Research and Technology 25 (1990) 1399-1404. DOI:10.1002/crat.2170251209.

6. Singh P, Anand A, Kumar V. Recent developments in biological activities of chalcones: A mini review. European Journal of Medicinal Chemistry 85 (2014) 758-777. https : //doi.org/10.1016/j.ejmech.2014.08.033.

7. Shettigar S, Chandrasekharan K, Umesh G,Sarojini BK.Studies on nonlinear optical parameters of bis-chalcone derivatives doped polymer. Polymer 47 (2006) 3565-3567. https://doi.org/10.1016/j.polymer.2006.03.062.

8. Prabhu SR, JayaramaA, Chandrasekharan K, UpadhyayaV, Ng SW. Synthesis, growth, structural characterization, Hirshfeld analysis and nonlinear optical studies of a methyl substituted chalcone. Journal of Molecular StructureVolume 1136 (2017) 244–252. https://doi.org/10.1016/j.molstruc.2017.01.069

9. Arshad MN, Al-DiesAM, Asiri AM, Khalid M, BirinjiAS, Al-Amry KA, BragaAAC. Synthesis, crystal structures, spectroscopic and nonlinear optical properties of chalcone derivatives: A combined experimental and theoretical study. Journal of Molecular StructureVolume 1141 ( 2017 ) 14 2–156. https://doi.org/10.1016/j.molstruc.2017.03.090.

10.Muhammad S, Al-Sehemi AG, Su Z, Xu H, Irfan A, ChaudhryAR. First principles study for the key electronic, optical and nonlinear optical properties of novel donor-acceptor chalcones. Journal of Molecular Graphics and Modelling. 72 (2017) 58-69. https://doi.org/10.1016/j.jmgm.2016.12.009.

11.Thabti S, Djedouani A, Rahmouni S, Touzani R, Bendaas A, Mousser H, Mousser A. Synthesis, X-ray crystal structures and catecholase activity investigation of new chalcone ligands. Journal of Molecular Structure 1102 (2015) 295-301. DOI: 10.1016/j.molstruc.2015.08.071.

12. Beltagy AM, Beltagy DM. Chemical composition of Ammi visnaga L. and New Cytotoxic Activity of its Constituents Khellin and Visnagin. Journal of Pharmaceutical Sciences and Research 7 (2015) 285-291.

13. Günaydın K, Beyazit N. The Chemical Investigations on the Ripe Fruits of Ammi visnaga (Lam.) Lamarck Growing in Turkey. Natural Product Research 18 (2004) 169-175. http://dx.doi.org/10.1080/14786410310001608091.

14 .Anrep GV, Barsoum GS, Kenawy MR. The Pharmacological Actions of the Crystalline Principles of Ammi visnaga Linn. Journal of Pharmacy and Pharmacology 1 (1949) 164-176. DOI:10.1111/j.2042-7158.1949.tb12395.x.

15. Schöberg A, Sina A. Khellin and Allied Compounds. Journal of American Chemical Society 72 (1950) 1611-1616.DOI:10.1021/ja01160a051.

16.Tay MG, Tiong MH, Chia YY, Kuan SHC, Liu ZQ.A Way to Improve Luminescent Efficiency of Bis-Chalcone Derivatives. Journal of Chemistry 2016 (2016) 1-8. http : //dx.doi.org/10.1155/2016/3608137.

17.Aksöz BE, Ertan R. Spectral Properties of Chalcones II. FABAD Journal of Pharmaceutical Sciences 37 (2012) 205-216.

18.Thirunarayanan G, Gopalakrishnan M, Vanangamudi G. IR and NMR spectral studies of 4-bromo-1-naphthyl chalcones-assessment of substituent effects. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 67 (2007) 1106-1112. DOI: 10.1016/j.saa.2006.09.034.

19.Mabry TJ, Markham KR, Thomas MB. The Ultraviolet Spectra of Chalcones and Aurones, in: The Systematic Identification of Flavonoids, Springer-Verlag, Berlin-Heidelberg-New York, pp. 227-250, 1970.

20. Kumari R, Varghese A, George L, Sudhakar YN. Effect of solvent polarity on the photophysical properties of chalcone derivatives. RSC Advances 7 (2017) 24204-24214. DOI: 10.1039/c7ra01705g.
Published
2017-12-22
How to Cite
Beyazit, N. (2017). The Synthesis and Spectral Properties of Benzofuran Derivative bis-Chalcone. Hittite Journal of Science & Engineering, 5(1), 69-73. Retrieved from https://www.hjse.hitit.edu.tr/hjse/index.php/HJSE/article/view/HJSE19030000067
Section
SCIENCE