Coumarins or benzo-2-pyrone derivatives are one of the most significant families of natural compounds and are also important in synthetic organic chemistry. They have been widely used as starting materials or precursor molecules in the pharmaceutical, perfumery and agrochemical industries, etc. Hydroxycoumarins are an important class of coumarin compounds that possess several physical, chemical and biological properties. Among the hydroxycoumarins, 3-hydroxycoumarin seems to be the most important because of its numerous chemical, photochemical and biological properties. However, this compound remains less well known compared to others of the same class such as 7-hydroxycoumarin and 4-hydroxycoumarin. This study is therefore devoted to 3-hydroxycoumarin and its applications. The main purpose of this review is to summarize and document the recent advances on 3-hydroxycoumarin, concerning the main routes of its synthesis, its reactivity, its applications in different fields of biology. Several methods for the synthesis of 3-hydroxycoumarin have been described in the literature, most of which use salicylic aldehyde and 1-(2-hydroxyphenyl)ethanone as starting compounds. Other synthesis pathways exist, but they are based on intermediate synthesis compounds. Concerning the reactivity of 3-hydroxycoumarin, many heterocyclic compounds obtained from 3-hydroxycoumarin have been reported in the literature. Among these heterocycles are pyrido[2,3-c]coumarin derivatives, chromeno[4,3-e][1,3]oxazine derivatives, dihydropyrano[2,3-c] chromenes and 3-coumarinyl carboxylates. Various researches have also concerned the biological properties of this compound. It appears from these numerous studies that 3-hdroxycoumarin is used in fields such as genetics, pharmacology, microbiology, etc.
Published in | American Journal of Heterocyclic Chemistry (Volume 6, Issue 1) |
DOI | 10.11648/j.ajhc.20200601.12 |
Page(s) | 6-15 |
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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. |
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Copyright © The Author(s), 2020. Published by Science Publishing Group |
Hydroxycoumarins, 3-Hydroxycoumarin, Synthesis Routes, Reactivity, Biological Properties
[1] | Sousa C. C. S., Morais V. M. F., Matos M. A. R. Energetics of the isomers: 3-and 4-hydroxycoumarin. J. Chem. Thermodyn. 2010, 42 (11): 1372–1378. |
[2] | 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): 1011–1018. |
[3] | Chohan Z. H., Shaikh A. U., Rauf A., Supuran C. T. Antibacterial, antifungal and cytotoxicproperties of novel N-substituted sulfonamides from 4-hydroxycoumarin. J. Enzym. Inhib. Med. Chem. 2006, 21, 741–748. |
[4] | 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, 4085–4087. |
[5] | Chiang C. C., Mouscadet J. F., Tsai H. J., Liu C. T., Hsu L. Y. Synthesis and HIV-1 integrase inhibition of novel bis-or tetracoumarin analogues. Chem. Pharm. Bull. 2007 55 (12): 1740–1743. |
[6] | Yoda J., Ouedraogo S., Saba A. 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 2019, 7 (4): 77-81. |
[7] | Sosso S., Yoda J., Djandé A., Coulomb B. (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): 17-25. |
[8] | De Araujo Leite J. C., de Castro Tainá X. M. T., Barbosa-Filho J. M., de Siqueira-Junior José P., Marques-Santos Luis F. Photoprotective effect of coumarin and 3-hydroxycoumarin in sea urchin gametes and embryonic cells. Journal of Photochemistry and Photobiology B: Biology 2015, 146, 44–51. |
[9] | Bailly F., Maurin C., Teissier E., Vezina H. and Cotelle P. Antioxidant properties of 3-hydroxycoumarin derivatives. Bioorganic & Medicinal Chemistry 12 (2004) 5611–5618. |
[10] | Trivedi K. N. and Sethna S. 3-hydroxycoumarin. J. Org. Chem. 1960., 25 (10) 1817. |
[11] | Dupont R. and Cotelle P. Reaction of aryl-2-hydroxypropenoic derivatives with boron tribromide. Tetrahedron Letters 2001, 42 (4): 597–600. |
[12] | Pavé G., Chalard P., Viaud-Massuard M.-C., Troin Y., Guillaumet G. New Efficient Synthesis of Pyrido[2,3-c] and Pyrido[3,2-c]coumarin Derivatives. Synlett. 2003, 7, 987–990. |
[13] | Gallina C. and Liberatori A. Condensation of 1,4-Diacetyl–2, 5-piperazinedione with aldehyde. Tetrahedron 1974, 30, 664. |
[14] | Shin C.-G., Nakajima Y., and Sato Y. facile synthesis and conversion of main skeleton of aspirochlorin to 3-aminocoumarin derivatives. Chemistry letters 1984, 1301-1304. |
[15] | Mondal A., Rana S., Mukhopadhyay C. One-pot, expeditious and chromatography-free synthesis of new chromeno[4,3-e][1,3]oxazine derivatives catalyzed by reusable TiO2 nanopowder at room temperature. Tetrahedron Letters 2014, 55 (24): 3498-3502. |
[16] | Kumar A., Maurya R. A., Sharma S. A., Ahmad P., Singh A. B., Bhatia G., Srivastava A. K. Pyranocoumarins: A New Class of Anti-Hyperglycemic and Anti-Dyslipidemic Agents Bioorg. Med. Chem. Lett. 2009, 19 (22): 6447-51. |
[17] | RajT., Bhatia R. K., Kapur, A., Sharma M., Saxena A. K., Ishar M. P. S. Cytotoxic Activity of 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones and 4-oxo-4H-chromene-3-carbothioic Acid N-phenylamides. Eur. J. Med. Chem. 2010, 45 (2): 790-4. |
[18] | Symeonidis T., Fylaktakidou K. C., Hadjipavlou-Litina D. J., Litinas K. E. Synthesis and Anti-Inflammatory Evaluation of Novel Angularly or Linearly Fused Coumarins. Eur. J. Med. Chem. 2009, 44 (12): 5012-7. |
[19] | Sanjay P., Pranabes B., Asish R. D., One-pot synthesis of dihydropyrano[2,3-c]chromenes via a three component coupling of aromatic aldehydes, malononitrile, and 3-hydroxycoumarin catalyzed by nano-structured ZnO in water: a green protocol. Tetrahedron Letters 2011, 52, 4636–4641. |
[20] | Tapase B. A., Suryawanshi V. S., Shinde D. N., Shinde B. D. Solvent Free Microwave Assisted O-Alkylation and Acylation of 4-Hydroxy Coumarin. Bull. Environ. Pharmacol. Life Sci. 2012, 1 (7): 30-33. |
[21] | AL-AYED A. S. Synthesis of New Substituted Chromen[4,3-c]pyrazol-4-ones and Their Antioxidant Activities. Molecules 2011, 16 (12): 10292-10302. |
[22] | Cravotto G., Tagliapietra S., Cappello R., Palmisano G., Currini M. and Bocalini M. Long-Chain 3-Acyl-4-hydroxycoumarins: Structure and Antibacterial Activity. Archiv der. Pharmazie 2006, 338 (3): 129-132. |
[23] | Cravotto G., Balliano G., Tagliapietra S., Oliaro-Bosso S., Nano G. M. Novel squalene-hopene cyclase inhibitors derived from hydroxycoumarins and hydroxyacetophenones. Chem. Pharm. Bull. 2004a 52 (10): 1171-1174. |
[24] | Cravotto G., Balliano G., Tagliapietra S., Palmisano G., Penoni A. Umbelliferone aminoalkyl derivatives, a new class of squalene-hopene cyclase inhibitors. J. Med. Chem. 2004b, 39 (11): 917-924. |
[25] | Stadlbauer W., Hojas G. Ring closure reactions of 3-arylhydrazonoalkyl-quinolin-2-ones to 1-aryl-pyrazolo [4,3-c] quinolin-2-ones. J. Heterocycl. Chem. 2004, 41 (5): 681-690. |
[26] | Kravchenko D. V., Chibisova T. A., Traven V. F. Intermolecular character of the Fris rearrangement in the series of acyloxycoumarins. Russ. J. Org. Chem. 1999, 35 (6): 899-909. |
[27] | Traven V. F., Manaev A. V., Safronova O. B., Chibisova T. A., Lysenko K. A., Antipin M. Y. Electronic structure of π systems: XVIII. Photoelectron spectrum and crystal structure of 3-acetyl-4-hydroxycoumarin. Russ. J. Gen. Chem. 2000, 70 (5): 798-808. |
[28] | Dholakia V. N., Parekh M. G., Trivedi N. K., Improved and rapid synthesis of new coumarinyl chalcone derivatives and their antiviral activity. Aust. J. Chem. 1968, 22, 345-2347. |
[29] | Akoun A., Djande A., Sessouma B., Saba A. and Kakou-Yao R. 4-[(4-Chlorophenyl)(hydroxy)methylidene]isochromane-1,3-dione. Acta Cryst. E67, 2011, 2269-2270. |
[30] | Akoun A., Djande A., Kakou-Yao R., Saba A. and A. J. Tenon. 2-Oxo-2H-chromen-4-yl 4-methylbenzoate. Acta Cryst. E69, 2013, 1081-1082. |
[31] | Rad-Maghadam K., Mohseni M., A Route to the Synthesis of Novel Coumarins. Monatshefte fur chemie 2004, 135 (7): 817-821. |
[32] | Djandé A., Cissé L., Yoda J., Kaboré L. and Duvernay F. Synthesis and fluorescence study of a series of 4-hydroxycoumarin o-acylation derivatives. world journal of pharmacy and pharmaceutical sciences 2019, 8 (1): 116-130. |
[33] | Saba Adama Thèse Unique, Recherche dans la série des sels de benzopyrylium: Synthèse et étude de la structure des sels de 2-benzopyrylium. UFR-SEA, Université de Ouagadougou (1996). |
[34] | Djandé A. Cisse L. Kaboré L., Saba A., Tine A. and Aycard J. P. Synthesis and fluorescence properties of 4-acylisochroman-1,3-diones. Heterocyclic communications 2008, 14 (4): 237-244. |
[35] | Schnekenburger J. Acyl derivatives of homophthalic acid anhydride. 2. on acyl derivatives of methylene-active dicarbonyl compounds. Arch Pharm Ber Dtsch Pharm Ges1965, 298, 4-18. |
[36] | Jules Yoda. Thèse unique (spécialité Chimie Organique): synthèse et étude des propriétés physicochimiques des carboxylates de 3-coumarinyle. UFR-SEA Université de Ouagadougou (2015). |
[37] | Yoda J., Chiavassa T. and Saba A. Fragmentations processes of 3-coumarinyl carboxylates in ESI/MS and their Correlation with the Electronic charges of their atoms. Research journal of chemical sciences 2014, 4 (4): 12-16. |
[38] | Ziki E., Yoda J., Djandé A., Saba A. and Kakou-Yao R. Crystal structure of 2-oxo-2H-chromen-3-yl propanoate. Acta Crystallographica Section E: Crystallographic Communications 2016, 72 (11): 1562-1564. |
[39] | 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, 41, 51-58. |
[40] | Abou A., Sessouma B., Djandé A., Saba A. and Kakou-Yao R. 2-Oxo-2H-chromen-4-yl 4-tert-butylbenzoate. Acta Cryst., E68, 2012, o537-o538. |
[41] | Abou A., Djandé A., Danger G., Saba A. and Kakou-Yao R. 2-Oxo-2H-chromen-4-yl 4-methoxybenzoate. Acta Cryst., E68, 2012, o3438-o3439. |
[42] | Abou A., Djandé A., Sessouma B., Saba A. and Kakou-Yao R. 2-Oxochromen-4-yl 4-(dimethylamino) benzoate. Acta Cryst., E67 (2011): o2269-o2270. |
[43] | Djandé A., Abou A., Kini B. F., Kambo K. R., Giorgi M. 2-Oxo-2H-chromen-7-yl 4-methylbenzoate IUCrData 2018; 3: x180927. |
[44] | Abou A., Yoda J., Djande A., Coussan S., Zoueu T. J. Crystal structure of 2-oxo-2H-chromen-7-yl 4-fluorobenzoate. Acta Cryst. 2018; E74: 761-765. |
[45] | Ouedraogo M., Abou A., Djandé A., Ouaric O., Zoueu J. T. 2-Oxo-2H-chromen-7-yl 4-tert-butylbenzoate. Acta Cryst. 2018; E74: 530-534. |
[46] | Djandé A., Abou A., Yoda J., Coussan S., Saba A. Synthesis, Spectrometric Characterization, X-Ray Study and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl 4-chlorobenzoate. American Journal of Chemistry 2019, 9 (5): 127-141. |
[47] | Kambo K. R., Sosso S., Djandé A., Kakou-Yao R. and Tenon A. J. 2-Oxo-2H-chromen-3-yl 4-tert-butylbenzoate. IUCrData. 2016, x161633. |
[48] | Kambo K. R., Sosso S., Mansilla-Koblavi F., Djandé A. and Kakou-Yao R. 2-Oxo-2H-chromen-3-yl benzoate. IUCrData. 2 2017, x170663. |
[49] | Ziki E., Sosso S., Mansilla-Koblavi F., Djandé, A. and Kakou-Yao, R. Crystal structure of 2-oxo-2H-chromen-3-yl 4-chlorobenzoate and Hirshfeld surface analysis. Acta Cryst. 2017, E73, 45–47. |
[50] | Ziki E., Sosso S., Cissé L., Guy E. B., Djandé A. and Kakou-Yao R. 2-Oxo-2H-chromen-3-yl 4-fluorobenzoate. IUCr Data. 2017, x170550. |
[51] | Matos M. J., Uriarte E., Santana L., Vilar S. Synthesis, NMR characterization, X-ray structural analysis and theoretical calculations of amide and ester derivatives of the coumarin scaffold. Journal of Molecular Structure 2014, 1041, 144–150. |
[52] | Schlicha M., Fornasier M., Niedduc M., Sinicoa C., Murgiab S., Rescignoc A. 3-hydroxycoumarin loaded vesicles for recombinant human tyrosinase inhibition in topical applications. Colloids and Surfaces B: Biointerfaces 2018, 171: 675–681. |
[53] | Asthana S., Zucca P., Vargiu V. A., Sanjust E., Ruggerone P. and Rescigno A. Structure−Activity Relationship Study of Hydroxycoumarins and Mushroom Tyrosinase. Journal of Agricultural and Food Chemistry 2015. 63 (32): 7236-44. |
[54] | De Andrade Gonçalves P., Dos Santos Junior M. C., Do Sacramento Sousa, C. et al. Study of sodium 3-hydroxycoumarin as inhibitors in vitro, in vivo and in silico of Moniliophthora perniciosa fungus. European Journal of Plant Pathology 2019, 153, 15–27. |
[55] | Kim, Y.; Hurst, G. B.; Study of Matrix and Polymer Substrate in MALDI-TOF Mass Spectrometry of DNA. Microchem. J. 2001, 70, 219–228. |
[56] | Zhang Z., Zhou L., Zhao S., Deng H. and Deng Q. 3-Hydroxycoumarin as a New Matrix for Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry of DNA. J Am Soc Mass Spectrom 2006, 17, 1665–1668. |
[57] | Wu K. J., Steding A., Becker H. Matrix-Assisted Laser Desorption Time-of Flight Mass Spectrometry of Oligonucleotides Using 3-Hydroxypicolinic Acid as an Ultraviolet-Sensitive Matrix. Rapid Commun. Mass Spectrom. 1993, 7, 142–146. |
[58] | Tang K., Taranenko N. I., Allman S. L., Chen C. H., Chang L. Y., Jacobson K. B. Picolinic Acid as a Matrix for Laser Mass Spectrometry of Nucleic Acids and Proteins. Rapid Commun. Mass Spectrom. 1994, 8, 673–677. |
[59] | Garcia B. A., Heaney P. J., Tang K. Improvement of the MALDI-TOF Analysis of DNA with Thin-Layer Matrix Preparation. Anal. Chem. 2002, 74, 2083–2091. |
[60] | Lavanant H., Lange C. Sodium-Tolerant Matrix for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry and Postsource Decay of Oligonucleotides. Rapid Commun. Mass Spectrom. 2002, 16, 1928–1933. |
[61] | Goodwin R. H., Pollock B. M. Ultraviolet absorption spectra of coumarin derivatives, Arch. Biochem. Biophys. 1954, 49, 1–6. |
[62] | Feltenmark S., Gautam N., Brunnström A., Griffiths W., Backman L., Edenius C., Lindbom L., Björkholm M., Claesson H. Eoxins are proinflammatory arachidonic acid metabolites produced via the 15-lipoxygenase-1 pathway in human eosinophils and mast cells. Proc. Natl Acad. Sci. USA 2008, 105 (2): 680–685. |
[63] | Hoult J. R. S., Paya M. Pharmacological and Biochemical Actions of Simple Coumarins: Natural Products With Therapeutic Potential. Gen. Pharmacol. 1996, 27 (4): 713-22. |
[64] | Kontogiorgis C. A., Hadjipavlou-Litina D. J. Synthesis and Antiinflammatory Activity of Coumarin Derivatives. J. Med. Chem. 2005, 48 (20): 6400-8. |
[65] | Jabbari A., Mousavian M., Seyedi S. M., Bakavoli M., Sadeghian H O-prenylated 3-carboxycoumarins as a Novel Class of 15-LOX-1 Inhibitors. PLoS ONE 2017, 12 (2): e0171789. |
[66] | Alavi S. J., Sadeghian H., Seyedi S. M., Salimi A., Eshghi H. A novel class of human 15-LOX-1 inhibitors based on 3-hydroxycoumarin. Chem Biol Drug Des. 2018, 00, 1–8. |
[67] | Sadeghian H., Jabbari A. 15-Lipoxygenase Inhibitors: A Patent Review. Expert Opin Ther Pat. 2016, 26 (1): 65-88. |
APA Style
Jules Yoda. (2020). Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound. American Journal of Heterocyclic Chemistry, 6(1), 6-15. https://doi.org/10.11648/j.ajhc.20200601.12
ACS Style
Jules Yoda. Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound. Am. J. Heterocycl. Chem. 2020, 6(1), 6-15. doi: 10.11648/j.ajhc.20200601.12
AMA Style
Jules Yoda. Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound. Am J Heterocycl Chem. 2020;6(1):6-15. doi: 10.11648/j.ajhc.20200601.12
@article{10.11648/j.ajhc.20200601.12, author = {Jules Yoda}, title = {Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound}, journal = {American Journal of Heterocyclic Chemistry}, volume = {6}, number = {1}, pages = {6-15}, doi = {10.11648/j.ajhc.20200601.12}, url = {https://doi.org/10.11648/j.ajhc.20200601.12}, eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20200601.12}, abstract = {Coumarins or benzo-2-pyrone derivatives are one of the most significant families of natural compounds and are also important in synthetic organic chemistry. They have been widely used as starting materials or precursor molecules in the pharmaceutical, perfumery and agrochemical industries, etc. Hydroxycoumarins are an important class of coumarin compounds that possess several physical, chemical and biological properties. Among the hydroxycoumarins, 3-hydroxycoumarin seems to be the most important because of its numerous chemical, photochemical and biological properties. However, this compound remains less well known compared to others of the same class such as 7-hydroxycoumarin and 4-hydroxycoumarin. This study is therefore devoted to 3-hydroxycoumarin and its applications. The main purpose of this review is to summarize and document the recent advances on 3-hydroxycoumarin, concerning the main routes of its synthesis, its reactivity, its applications in different fields of biology. Several methods for the synthesis of 3-hydroxycoumarin have been described in the literature, most of which use salicylic aldehyde and 1-(2-hydroxyphenyl)ethanone as starting compounds. Other synthesis pathways exist, but they are based on intermediate synthesis compounds. Concerning the reactivity of 3-hydroxycoumarin, many heterocyclic compounds obtained from 3-hydroxycoumarin have been reported in the literature. Among these heterocycles are pyrido[2,3-c]coumarin derivatives, chromeno[4,3-e][1,3]oxazine derivatives, dihydropyrano[2,3-c] chromenes and 3-coumarinyl carboxylates. Various researches have also concerned the biological properties of this compound. It appears from these numerous studies that 3-hdroxycoumarin is used in fields such as genetics, pharmacology, microbiology, etc.}, year = {2020} }
TY - JOUR T1 - Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound AU - Jules Yoda Y1 - 2020/08/18 PY - 2020 N1 - https://doi.org/10.11648/j.ajhc.20200601.12 DO - 10.11648/j.ajhc.20200601.12 T2 - American Journal of Heterocyclic Chemistry JF - American Journal of Heterocyclic Chemistry JO - American Journal of Heterocyclic Chemistry SP - 6 EP - 15 PB - Science Publishing Group SN - 2575-5722 UR - https://doi.org/10.11648/j.ajhc.20200601.12 AB - Coumarins or benzo-2-pyrone derivatives are one of the most significant families of natural compounds and are also important in synthetic organic chemistry. They have been widely used as starting materials or precursor molecules in the pharmaceutical, perfumery and agrochemical industries, etc. Hydroxycoumarins are an important class of coumarin compounds that possess several physical, chemical and biological properties. Among the hydroxycoumarins, 3-hydroxycoumarin seems to be the most important because of its numerous chemical, photochemical and biological properties. However, this compound remains less well known compared to others of the same class such as 7-hydroxycoumarin and 4-hydroxycoumarin. This study is therefore devoted to 3-hydroxycoumarin and its applications. The main purpose of this review is to summarize and document the recent advances on 3-hydroxycoumarin, concerning the main routes of its synthesis, its reactivity, its applications in different fields of biology. Several methods for the synthesis of 3-hydroxycoumarin have been described in the literature, most of which use salicylic aldehyde and 1-(2-hydroxyphenyl)ethanone as starting compounds. Other synthesis pathways exist, but they are based on intermediate synthesis compounds. Concerning the reactivity of 3-hydroxycoumarin, many heterocyclic compounds obtained from 3-hydroxycoumarin have been reported in the literature. Among these heterocycles are pyrido[2,3-c]coumarin derivatives, chromeno[4,3-e][1,3]oxazine derivatives, dihydropyrano[2,3-c] chromenes and 3-coumarinyl carboxylates. Various researches have also concerned the biological properties of this compound. It appears from these numerous studies that 3-hdroxycoumarin is used in fields such as genetics, pharmacology, microbiology, etc. VL - 6 IS - 1 ER -