Coumarins are the most important oxygenated heterocyclic of natural compounds. They are widely used as raw materials in many areas such as agrochemical, perfume, pharmaceutical industries. They therefore have several physical, chemical and biological properties. In order to enlarge this family of compounds and elucidate almost all of its properties, researchers have developed various synthetic methods that are not very complex and less expensive. Thus, from 4-hydroxycoumarin we have synthesized a series of 3-acyl-4-hydroxycoumarins by C-acylation. This study is therefore dedicated to the reactivity of 3-acyl-4-hydroxycoumarins. The synthesized coumarins showed a high reaction potential based on the chemical functions present in their structures. To enhance them later, we can try to graft other functions which can be the subject of several transformations such as: condensation, functionalization, cyclization, acylation. So to access more interesting new poly-functionalized compounds both at the reactivity and biological level. These molecules (3-acyl-4-hydroxycoumarins) being new, very little information is known on their physicochemical behavior in writings. On the other hand, the reactivity of molecules with similar structures to those of acyl-hydroxycoumarins such as 4-acylisochroman-1,3-diones and 3-acetyl-4-hydroxycoumarin have been the subject of scientists’ work. It emerges from this study that 3-acyl-4-hydroxycoumarins shows strong chemical reactivity which can be used biologically.
| Published in | American Journal of Heterocyclic Chemistry (Volume 7, Issue 2) |
| DOI | 10.11648/j.ajhc.20210702.13 |
| Page(s) | 33-38 |
| 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), 2024. Published by Science Publishing Group |
4-hydroxycoumarins, C-acylation, Acyl-hydroxycoumarins, Heterocyclic Compound
| [1] | Akoun, J. Yoda, A. Djandé, S. Coussan, and T. J. Zoueu, “2-oxo-2H-chromen-7-yl 4-fluorobenzoate,” Acta Cryst, vol. 74, pp. 761–765, 2018. |
| [2] | P. Siwach and P. Sen, “Synthesis and fluorescence properties of Ag nanoparticles,” Solid State Commun., vol. 148, no. 5–6, pp. 221–225, 2008. |
| [3] | Djandé, L. Cissé, J. Yoda, L. Kaboré, and F. Duvernay, “Synthesis and fluorescence study of a series of 4-hydroxycoumarin O-acylation derivatives.,” World J. Pharm. Pharm. Sci., vol. 8, no. 1, pp. 116–130, 2019. |
| [4] | J. Yoda et al., “Etude de l ’ effet de solvant sur la fluorescence des carboxylates de 3-coumarinyle,” pp. 9–14, 2018. |
| [5] | J. Yoda, S. Ouédraogo, and A. 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., vol. 7, no. 4, p. 77, 2019. |
| [6] | J. Yoda, “Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound,” Am. J. Heterocycl. Chem., vol. 6, no. 1, p. 6, 2020. |
| [7] | S. SOSSO, “Synthèse, Caractérisation Structurale et Etudes de la Fluorescence et du Pouvoir Reducteur d’une série de Composés D’Acylation de la Chroman-2,3-dione,” Université Joseph KI-ZERBO, 2019. |
| [8] | S. Siaka, J. Yoda, A. Djandé, and B. Coulomb, “(Coumarin-3-yl) -benzoates as a Series of New Fluorescent Compounds: Synthesis, Characterization and Fluorescence Properties in the Solid State,” vol. 8, no. 2, pp. 17–25, 2018. |
| [9] | Y. Bakouan, B. Sessouma, and L. Tarpaga, “Synthèses et caractérisation d ’ une série de nouveaux composés,” pp. 23–29, 2020. |
| [10] | J. Schnekenburger, “NRM and AM1 Study of the Tautomeric Equilibrium of Isochroman-1,2-dione,” Arch. Pharm., vol. 4, pp. 411–423, 1965. |
| [11] | J. Schnekenburger, “NRM and AM1 Study of the Tautomeric Equilibrium of Isochroman-1,2-dione,” Arch. Pharm., vol. 4, pp. 715–722, 1965. |
| [12] | Saba, F. S. Sib, and J. P. Aycard, “The synthesis of aromatic 3-carboxy-DIKETONES,” Bull. Chem. Soc. Ethiop, 1995. |
| [13] | F. Bihel, R. Faure, and J. L. Kraus, “Reactivity studies of 3-alkoxy-7-amino-4-chloroisocoumarins (β-amyloid peptide inhibitors) versus different classes of amines,” Org. Biomol. Chem., vol. 1, no. 5, pp. 800–802, 2003. |
| [14] | A Djandé, “Etude des propriétés physico-chimiques des 4-acylisochroman-1,3-diones,” Université de Ouagadougou, 2008. |
| [15] | W. Stadlbauer and G. Hojas, “Ring closure reactions of 3-arylhydrazonoalkyl-quinolin-2-ones to 1-aryl-pyrazolo[4,3-c]quinolin-2-ones,” J. Heterocycl. Chem., vol. 41, no. 5, pp. 681–690, 2004. |
| [16] | J. Li, X. Li, and S. Wang, “Synthesis, photoluminescent behaviors, and theoretical studies of two novel ketocoumarin derivatives,” Spectrochim. Acta - Part A Mol. Biomol. Spectrosc., vol. 88, pp. 31–36, 2012. |
| [17] | Y. S. Chen, P. Y. Kuo, T. L. Shie, and D. Y. Yang, “Structure, reactivity, and application of some triketone derivatives,” Tetrahedron, vol. 62, no. 40, pp. 9410–9416, 2006. |
| [18] | S. Sukdolak, S. Solujić, N. Manojlović, N. Vuković, and L. Krstić, “Hantzsch reaction of 3-(2-bromoacetyl)-4-hydroxy-chromen-2-one. Synthesis of 3-(thiazol-4-yl)-4-hydroxy coumarines,” J. Heterocycl. Chem., vol. 41, no. 4, pp. 593–596, 2004. |
| [19] | T. Kappe, R. Aigner, P. Roschger, B. Schnell, and W. Stadibauer, “A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid,” Tetrahedron, vol. 51, no. 47, pp. 12923–12928, 1995. |
| [20] | M. Kolb, “Synthetic communications: An international journal for rapid communication of synthetic organic chemistry,” Synth. Commun., vol. 23, no. 1, p. vii, 1993. |
| [21] | S. Al-Ayed, “Synthesis of new substituted chromen-[4,3-c]-pyrazol-4-ones and their antioxidant activities,” Molecules, vol. 16, no. 12, pp. 10292–10302., 2011. |
| [22] | N. Hamdi, C. Fischmeister, M. C. Puerta, and P. Valerga, “A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities,” Med. Chem. Res., vol. 20, no. 4, pp. 522–530, 2011. |
| [23] | K. Patel et al., “Synthesis of Some Coumarinyl Chalcones and their Antiproliferative Activity Against Breast Cancer Cell Lines,” Lett. Drug Des. Discov., vol. 8, no. 4, pp. 308–311, 2012. |
| [24] | M. Abdelhafez, K. M. Amin, R. Z. Batran, T. J. Maher, S. A. Nada, and S. Sethumadhavan, “Synthesis, anticoagulant and PIVKA-II induced by new 4-hydroxycoumarin derivatives,” Bioorganic Med. Chem., vol. 18, no. 10, pp. 3371–3378, 2010. |
| [25] | M. Mladenovic, N. Vukovic, N. Niciforovic, S. Sukdolak, and S. Solujic, “Synthesis and molecular descriptor characterization of novel 4-hydroxy-chromene-2-one derivatives as antimicrobial agents,” Molecules, vol. 14, no. 4, pp. 1495–1512, 2009. |
| [26] | Z. N. Siddiqui, M. Asad, and S. Praveen, “Synthesis and biological activity of heterocycles from chalcone,” Med. Chem. Res., vol. 17, no. 2–7, pp. 318–325, 2008. |
| [27] | Z. N. Siddiqui and T. N. M. Musthafa, “An efficient and novel synthesis of chromonyl chalcones using recyclable Zn(l-proline)2 catalyst in water,” Tetrahedron Lett., vol. 52, no. 31, pp. 4008–4013, 2011. |
| [28] | “separation and determination of uranium and thorium with 3-acetyl-4-hydroxy- uranyl ion is generally determined as oxide after the precipitation of ammonium diuranate. This method is accurate when other metals precipitated by ammonia are absent, but car,” Uranium, vol. 4, pp. 13–16, 1960. |
| [29] | U. Galm, S. Heller, S. Shapiro, M. Page, S. M. Li, and L. Heide, “Antimicrobial and DNA Gyrase-Inhibitory Activities of Novel Clorobiocin Derivatives Produced by Mutasynthesis,” Antimicrob. Agents Chemother., vol. 48, no. 4, pp. 1307–1312, 2004. |
| [30] | Kontogiorgis, A. Detsi, and D. Hadjipavlou-Litina, “Coumarin-based drugs: A patent review (2008 - present),” Expert Opin. Ther. Pat., vol. 22, no. 4, pp. 437–454, 2012. |
APA Style
Youssoufou Bakouan, Bintou Sessouma, Têeda Hamidou Ganamé, Lassané Tarpaga, Jules Yoda, et al. (2021). Some Aspects of the Reactivity of 3-acyl-4-hydroxycoumarins. American Journal of Heterocyclic Chemistry, 7(2), 33-38. https://doi.org/10.11648/j.ajhc.20210702.13
ACS Style
Youssoufou Bakouan; Bintou Sessouma; Têeda Hamidou Ganamé; Lassané Tarpaga; Jules Yoda, et al. Some Aspects of the Reactivity of 3-acyl-4-hydroxycoumarins. Am. J. Heterocycl. Chem. 2021, 7(2), 33-38. doi: 10.11648/j.ajhc.20210702.13
AMA Style
Youssoufou Bakouan, Bintou Sessouma, Têeda Hamidou Ganamé, Lassané Tarpaga, Jules Yoda, et al. Some Aspects of the Reactivity of 3-acyl-4-hydroxycoumarins. Am J Heterocycl Chem. 2021;7(2):33-38. doi: 10.11648/j.ajhc.20210702.13
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.ajhc.20210702.13,
author = {Youssoufou Bakouan and Bintou Sessouma and Têeda Hamidou Ganamé and Lassané Tarpaga and Jules Yoda and Karifa Bayo},
title = {Some Aspects of the Reactivity of 3-acyl-4-hydroxycoumarins},
journal = {American Journal of Heterocyclic Chemistry},
volume = {7},
number = {2},
pages = {33-38},
doi = {10.11648/j.ajhc.20210702.13},
url = {https://doi.org/10.11648/j.ajhc.20210702.13},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20210702.13},
abstract = {Coumarins are the most important oxygenated heterocyclic of natural compounds. They are widely used as raw materials in many areas such as agrochemical, perfume, pharmaceutical industries. They therefore have several physical, chemical and biological properties. In order to enlarge this family of compounds and elucidate almost all of its properties, researchers have developed various synthetic methods that are not very complex and less expensive. Thus, from 4-hydroxycoumarin we have synthesized a series of 3-acyl-4-hydroxycoumarins by C-acylation. This study is therefore dedicated to the reactivity of 3-acyl-4-hydroxycoumarins. The synthesized coumarins showed a high reaction potential based on the chemical functions present in their structures. To enhance them later, we can try to graft other functions which can be the subject of several transformations such as: condensation, functionalization, cyclization, acylation. So to access more interesting new poly-functionalized compounds both at the reactivity and biological level. These molecules (3-acyl-4-hydroxycoumarins) being new, very little information is known on their physicochemical behavior in writings. On the other hand, the reactivity of molecules with similar structures to those of acyl-hydroxycoumarins such as 4-acylisochroman-1,3-diones and 3-acetyl-4-hydroxycoumarin have been the subject of scientists’ work. It emerges from this study that 3-acyl-4-hydroxycoumarins shows strong chemical reactivity which can be used biologically.},
year = {2021}
}
TY - JOUR T1 - Some Aspects of the Reactivity of 3-acyl-4-hydroxycoumarins AU - Youssoufou Bakouan AU - Bintou Sessouma AU - Têeda Hamidou Ganamé AU - Lassané Tarpaga AU - Jules Yoda AU - Karifa Bayo Y1 - 2021/12/07 PY - 2021 N1 - https://doi.org/10.11648/j.ajhc.20210702.13 DO - 10.11648/j.ajhc.20210702.13 T2 - American Journal of Heterocyclic Chemistry JF - American Journal of Heterocyclic Chemistry JO - American Journal of Heterocyclic Chemistry SP - 33 EP - 38 PB - Science Publishing Group SN - 2575-5722 UR - https://doi.org/10.11648/j.ajhc.20210702.13 AB - Coumarins are the most important oxygenated heterocyclic of natural compounds. They are widely used as raw materials in many areas such as agrochemical, perfume, pharmaceutical industries. They therefore have several physical, chemical and biological properties. In order to enlarge this family of compounds and elucidate almost all of its properties, researchers have developed various synthetic methods that are not very complex and less expensive. Thus, from 4-hydroxycoumarin we have synthesized a series of 3-acyl-4-hydroxycoumarins by C-acylation. This study is therefore dedicated to the reactivity of 3-acyl-4-hydroxycoumarins. The synthesized coumarins showed a high reaction potential based on the chemical functions present in their structures. To enhance them later, we can try to graft other functions which can be the subject of several transformations such as: condensation, functionalization, cyclization, acylation. So to access more interesting new poly-functionalized compounds both at the reactivity and biological level. These molecules (3-acyl-4-hydroxycoumarins) being new, very little information is known on their physicochemical behavior in writings. On the other hand, the reactivity of molecules with similar structures to those of acyl-hydroxycoumarins such as 4-acylisochroman-1,3-diones and 3-acetyl-4-hydroxycoumarin have been the subject of scientists’ work. It emerges from this study that 3-acyl-4-hydroxycoumarins shows strong chemical reactivity which can be used biologically. VL - 7 IS - 2 ER -
Information
Email: