Natural or synthetic coumarins are of great interest, since many of them show prominent biological activity and photochemical characteristics. In particular, hydroxycoumarins and their derivatives have been extensively studied in various fields such as biology, medicine, physics and chemistry. Among the well-known compounds is 7-hydroxycoumarin, also known as umbelliferone and 4-hydroxycoumarin. Against 3-hydroxycoumarin and its derivatives are less known and studied. In this study, new acyl derivatives were synthesized from 3-hydroxycoumarin or chromen-2,3-dione its tautomeric form and chloride acid in the presence of an appropriated base. The structures of the newly obtained compounds were confirmed by elemental analysis, mass spectrometry (MS), IR and NMR spectrometry and X-ray diffractometry. In addition, the fluorescence properties of the titre compounds were also studied in both liquid and solid state. In liquid media, the study concerned their behaviour in fluorescence emission spectrometry in 6 solvents of different polarities. The new heterocyclic compounds have been successfully synthesized. Fluorescence spectrum analyses show that these compounds are all fluorescent in both solid and liquid state with varying fluorescence intensities (IF). On solvatochromic analyses, it appears that the behaviour of the spectrum depends strongly on the solvent. The fluorescence intensity and wavelength (λem) vary depending on the nature of the substituent (R) and especially that of the solvent. It should also be noted that chloroform is the solvent that most enhances the fluorescence of the compounds.
| Published in | Science Journal of Chemistry (Volume 7, Issue 4) |
| DOI | 10.11648/j.sjc.20190704.12 |
| Page(s) | 77-81 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2019. Published by Science Publishing Group |
Coumarins, 3-Hydroxycoumarin, Chromen-2, 3-Dione, Fluorescence Properties
| [1] | Walshe M., Howarth J., Kelly M. T., O’Kennedy R., & Smyth M. R. The preparation of a molecular imprinted polymer to 7-hydroxycoumarin and its use as a solid-phase extraction material. Journal of Pharmaceutical and Biomedical Analysis 1997, 16 (2): pp. 319–325. |
| [2] | Sosso Siaka, Jules Yoda, Abdoulaye Djandé, Bruno Coulomb. (Coumarin-3-yl)-benzoates as a Series of New Fluorescent Compounds: Synthesis, Characterization and Fluorescence Properties in the Solid State. American Journal of Organic Chemistry 2018, 8 (2): pp. 17-25. |
| [3] | Jae-Chul Jung and Oee-Sook Park. Synthetic Approaches and Biological Activities of 4-Hydroxycoumarin Derivatives. Molecules 2009, 14 (11): pp. 4790-4803. |
| [4] | Symeonidis T., Chamilos M., Hadjipavlou-Litina D. J., Kallitsakis M., & Litinas K. E. Synthesis of hydroxycoumarins and hydroxybenzo [f]-or [h]coumarins as lipid peroxidation inhibitors. Bioorganic & Medicinal Chemistry Letters 2009, 19 (4): pp. 1139–1142. |
| [5] | Joseph K. S., Moser A. C., Basiaga S. B. G., Schiel J. E., Hage D. S. Evaluation of alternatives to warfarin as probes for Sudlow site I of human serum albumin. J. Chromatogr. A 2009, 1216 (16): pp. 3492–500. |
| [6] | Au N., Rettie A E. Pharmacogenomics of 4-hydroxycoumarin anticoagulants. Drug Metab. Rev. 2008, 40 (2): pp. 355–375. |
| [7] | Vukovic N., Sukdolak S., Solujic S., Niciforovic N. Substituted imino and amino derivatives of 4-hydroxycoumarins as novel antioxidant, antibacterial and antifungal agents: synthesis and in vitro assessments. Food Chem. 2010 120 (4): pp. 1011–1018. |
| [8] | Dong Y., Nakagawa-Goto K., Lai C., Morris-Natschke S., Bastow K., Lee K. Antitumor agents 278. 4-Amino-2H-benzo [h]chromen-2-one (abo) analogs as potent in vitro anticancer agents. Bioorg. Med. Chem. Lett. 2010, 20, pp. 4085–4087. |
| [9] | Kielbus M., Skalicka-Wozniak K., Grabarska A., Jeleniewicz W., Dmoszynska-Graniczka M., Marston M., Polberg K., Gawda P., Klatka J., Stepulak A., 7-substituted coumarins inhibit proliferation and migration of laryngeal cancer cells in vitro, Anticancer Res. 2013, 33, pp. 4347–4356. |
| [10] | Rauf A., Khan R., Khan H., Pervez S., Pirzada A. S. In vivo antinociceptive and anti-inflammatory activities of umbelliferone isolated from Potentilla evestita, Nat. Prod. Res. 2014, 28, pp. 1371–1374. |
| [11] | Luchini A. C., Rodrigues-Orsi P., Cestari S. H., Seito L. N., Witaicenis A., Pellizzon C. H., Di Setasi L. C. Intestinal Anti-inflammatory Activity of Coumarin and 4-Hydroxycoumarin in the Trinitrobenzene sulphonic Acid Model of Rat Colitis. Biol. Pharm. Bull. 2008, 31 (7): pp. 1343-1350. |
| [12] | Huang L, Yuan X, Yu D, Lee K, Ho Chen C. Mechanism of action and resistant profile of anti-HIV-1 coumarin derivatives. Virology 2005, 332, pp. 623–628. |
| [13] | Kirkiacharian B. S., Clercq E., Kurkjian R., Pannecouque C. J. Pharm. Chem. 2008, 42, pp. 265–270. |
| [14] | Liang C., Jiang H., Zhou, Z., Lei D., Xue Y., Yao Q. Ultrasound-promoted greener synthesis of novel trifurcate 3-substituted-chroman-2, 4-dione derivatives and their drug-likeness evaluation. Molecules 2012, 17, pp. 14146–14158. |
| [15] | Yoda J., Chiavassa T. and Saba A. Fragementations processes of 3-coumarinyl carboxylates in ESI/ MS and their correlation with the electronic charges of their atoms, Res. J. Chem. Sci. 2014, 4 (4): pp. 12-16. |
| [16] | Yoda J., Djandé A., Kaboré L., House P., Traoré H. and Saba A. EIMS and AM1 study of the fragmentations of 3-coumarinyl Carboxylates: Interpretation from electronic charges of atoms. J. Soc. Ouest-Afr. Chim. 2016, 041, pp. 51-58. |
| [17] | Ziki E., Yoda J., Djande A., Saba A. and Kakou-Yao R. Crystal structure of 2-oxo-2H-chromen-3-ylpropanoate. Acta Cryst. 2016, E72, pp. 1562–1564. |
| [18] | Yoda J., Cissé L., Saba A. Synthesis and fluorescence properties of 3-coumarinyl carboxylates. Res. J. Chem. Sci. 2018, 8 (8): pp. 16-19. |
| [19] | Yoda J., Cissé L., Djandé A., Kaboré L., Saba A. Solvent effect studies on the fluorescence spectra of 3-coumarinyl Carboxylates. J. Soc. Ouest-Afr. Chim. 2018, 046, pp. 9-14. |
APA Style
Jules Yoda, Salfo Ouédraogo, Adama Saba. (2019). 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Science Journal of Chemistry, 7(4), 77-81. https://doi.org/10.11648/j.sjc.20190704.12
ACS Style
Jules Yoda; Salfo Ouédraogo; Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci. J. Chem. 2019, 7(4), 77-81. doi: 10.11648/j.sjc.20190704.12
AMA Style
Jules Yoda, Salfo Ouédraogo, Adama Saba. 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties. Sci J Chem. 2019;7(4):77-81. doi: 10.11648/j.sjc.20190704.12
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Download@article{10.11648/j.sjc.20190704.12,
author = {Jules Yoda and Salfo Ouédraogo and Adama Saba},
title = {2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties},
journal = {Science Journal of Chemistry},
volume = {7},
number = {4},
pages = {77-81},
doi = {10.11648/j.sjc.20190704.12},
url = {https://doi.org/10.11648/j.sjc.20190704.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20190704.12},
abstract = {Natural or synthetic coumarins are of great interest, since many of them show prominent biological activity and photochemical characteristics. In particular, hydroxycoumarins and their derivatives have been extensively studied in various fields such as biology, medicine, physics and chemistry. Among the well-known compounds is 7-hydroxycoumarin, also known as umbelliferone and 4-hydroxycoumarin. Against 3-hydroxycoumarin and its derivatives are less known and studied. In this study, new acyl derivatives were synthesized from 3-hydroxycoumarin or chromen-2,3-dione its tautomeric form and chloride acid in the presence of an appropriated base. The structures of the newly obtained compounds were confirmed by elemental analysis, mass spectrometry (MS), IR and NMR spectrometry and X-ray diffractometry. In addition, the fluorescence properties of the titre compounds were also studied in both liquid and solid state. In liquid media, the study concerned their behaviour in fluorescence emission spectrometry in 6 solvents of different polarities. The new heterocyclic compounds have been successfully synthesized. Fluorescence spectrum analyses show that these compounds are all fluorescent in both solid and liquid state with varying fluorescence intensities (IF). On solvatochromic analyses, it appears that the behaviour of the spectrum depends strongly on the solvent. The fluorescence intensity and wavelength (λem) vary depending on the nature of the substituent (R) and especially that of the solvent. It should also be noted that chloroform is the solvent that most enhances the fluorescence of the compounds.},
year = {2019}
}
TY - JOUR T1 - 2-oxo-2H-chromen-3-yl Propionate and 2-oxo-2H-chromen-3-yl Acetate: Short-step Synthesis, Characterization and Fluorescence Properties AU - Jules Yoda AU - Salfo Ouédraogo AU - Adama Saba Y1 - 2019/10/23 PY - 2019 N1 - https://doi.org/10.11648/j.sjc.20190704.12 DO - 10.11648/j.sjc.20190704.12 T2 - Science Journal of Chemistry JF - Science Journal of Chemistry JO - Science Journal of Chemistry SP - 77 EP - 81 PB - Science Publishing Group SN - 2330-099X UR - https://doi.org/10.11648/j.sjc.20190704.12 AB - Natural or synthetic coumarins are of great interest, since many of them show prominent biological activity and photochemical characteristics. In particular, hydroxycoumarins and their derivatives have been extensively studied in various fields such as biology, medicine, physics and chemistry. Among the well-known compounds is 7-hydroxycoumarin, also known as umbelliferone and 4-hydroxycoumarin. Against 3-hydroxycoumarin and its derivatives are less known and studied. In this study, new acyl derivatives were synthesized from 3-hydroxycoumarin or chromen-2,3-dione its tautomeric form and chloride acid in the presence of an appropriated base. The structures of the newly obtained compounds were confirmed by elemental analysis, mass spectrometry (MS), IR and NMR spectrometry and X-ray diffractometry. In addition, the fluorescence properties of the titre compounds were also studied in both liquid and solid state. In liquid media, the study concerned their behaviour in fluorescence emission spectrometry in 6 solvents of different polarities. The new heterocyclic compounds have been successfully synthesized. Fluorescence spectrum analyses show that these compounds are all fluorescent in both solid and liquid state with varying fluorescence intensities (IF). On solvatochromic analyses, it appears that the behaviour of the spectrum depends strongly on the solvent. The fluorescence intensity and wavelength (λem) vary depending on the nature of the substituent (R) and especially that of the solvent. It should also be noted that chloroform is the solvent that most enhances the fluorescence of the compounds. VL - 7 IS - 4 ER -
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