dc.contributor | Granados Oliveros, Gilma | |
dc.contributor | Síntesis Orgánica Sostenible | |
dc.creator | Sánchez Sierra, Christian Camilo | |
dc.date.accessioned | 2023-08-08T21:50:59Z | |
dc.date.accessioned | 2023-08-25T13:57:39Z | |
dc.date.available | 2023-08-08T21:50:59Z | |
dc.date.available | 2023-08-25T13:57:39Z | |
dc.date.created | 2023-08-08T21:50:59Z | |
dc.date.issued | 2021-11-22 | |
dc.identifier | https://repositorio.unal.edu.co/handle/unal/84501 | |
dc.identifier | Universidad Nacional de Colombia | |
dc.identifier | Repositorio Institucional Universidad Nacional de Colombia | |
dc.identifier | https://repositorio.unal.edu.co/ | |
dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/8427035 | |
dc.description.abstract | Three new and novel hybrids of coumarin pyridines with a donor π acceptor system were synthesized in a 5-step series, without metal catalysts or special experimental conditions. These compounds were characterized by melting point, IR-TF, 1H NMR, APT and 13C, UV-Vis spectroscopy and fluorescence. Also, mass spectrometry. The photophysical characteristics of the pyridine coumarin derivatives were studied, showing that they are strong emitters of blue light when excited at a λem of 300 nm, reaching quantum yields between 10 and 12%, these were evaluated against various metal ions, showing a high selectivity for Al3+. (Texto tomado de la fuente) | |
dc.description.abstract | Tres nuevos y novedosos híbridos de cumarín piridinas con un sistema donor π aceptor fueron sintetizados en una serie de 5 pasos, sin catalizadores metálicos, ni condiciones experimentales especiales. Estos compuestos fueron caracterizados por punto de fusión, IR-TF, RMN 1H, APT y 13C, espectroscopía de UV-Vis y fluorescencia. Además, de espectrometría de masas. Se estudiaron las características fotofísicas de los derivados cumarín piridínicos mostrando ser unos fuertes emisores de luz azul al ser excitados a una λem de 300 nm llegando a tener rendimientos cuánticos entre el 10 y 12 %, estos fueron evaluados frente a diversos iones metálicos, mostrando una alta selectividad por Al3+. | |
dc.language | spa | |
dc.publisher | Bogotá - Ciencias - Maestría en Ciencias - Química | |
dc.publisher | Facultad de Administración | |
dc.publisher | Bogotá, Colombia | |
dc.publisher | Universidad Nacional de Colombia - Sede Bogotá | |
dc.relation | (1) Venugopala, K. N.; Rashmi, V.; Odhav, B. Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity. Biomed Res. Int. 2013, 2013 | |
dc.relation | (2) BERENBAUM, M. R. Coumarins. Herbiv. their Interact. with Second. Plant Metab. 1991, I, 221–249. | |
dc.relation | (3) Liu, B. Y.; Zhang, C.; Zeng, K. W.; Li, J.; Guo, X. Y.; Zhao, M. B.; Tu, P. F.; Jiang, Y. Anti-Inflammatory Prenylated Phenylpropenols and Coumarin Derivatives from Murraya Exotica. J. Nat. Prod. 2018, 81 (1), 22–33. | |
dc.relation | (4) Mileski, K. S.; Trifunović, S. S.; Ćirić, A. D.; Šakić, Ž. M.; Ristić, M. S.; Todorović, N. M.; Matevski, V. S.; Marin, P. D.; Tešević, V. V.; Džamić, A. M. Research on Chemical Composition and Biological Properties Including Antiquorum Sensing Activity of Angelica Pancicii Vandas Aerial Parts and Roots. J. Agric. Food Chem. 2017, 65 (50). | |
dc.relation | (5) Wang, Y. S.; Li, B. T.; Liu, S. X.; Wen, Z. Q.; Yang, J. H.; Zhang, H. Bin; Hao, X. J. Anisucoumaramide, a Bioactive Coumarin from Clausena Anisum-Olens. J. Nat. Prod. 2017, 80 (4), 798–804. | |
dc.relation | (6) Tee, K. H.; Ee, G. C. L.; Ismail, I. S.; Karunakaran, T.; Teh, S. S.; Jong, V. Y. M.; Mohd Nor, S. M. A New Coumarin from Stem Bark of Calophyllum Wallichianum. Nat. Prod. Res. 2018, 6419, 2565–2570. | |
dc.relation | (7) Chang, F. R.; Li, P. S.; Huang Liu, R.; Hu, H. C.; Hwang, T. L.; Lee, J. C.; Chen, S. L.; Wu, Y. C.; Cheng, Y. Bin. Bioactive Phenolic Components from the Twigs of Atalantia Buxifolia. J. Nat. Prod. 2018, 81 (7), 1534–1539. | |
dc.relation | 8) Kamauchi, H.; Noji, M.; Kinoshita, K.; Takanami, T.; Koyama, K. Coumarins with an Unprecedented Tetracyclic Skeleton and Coumarin Dimers from Chemically Engineered Extracts of a Marine-Derived Fungus. Tetrahedron 2018, 74 (23), 2846–2856. | |
dc.relation | (9) Ma, Q. G.; Wei, R. R.; Yang, M.; Huang, X. Y.; Wang, F.; Sang, Z. P.; Liu, W. M.; Yu, Q. Molecular Characterization and Bioactivity of Coumarin Derivatives from the Fruits of Cucumis Bisexualis. J. Agric. Food Chem. 2018, 66 (22), 5540–5548. | |
dc.relation | (10) Frost et Al. - A Coumarin as a Fluorescent Compound in Scorpion Cuticle. Scorpions. 2001. 365-368. | |
dc.relation | (11) Sandhu, S.; Bansal, Y.; Silakari, O.; Bansal, G. Coumarin Hybrids as Novel Therapeutic Agents. Bioorganic Med. Chem. 2014, 22 (15), 3806–3814. | |
dc.relation | (12) Roncalés, F. J. Tratamiento Anticoagulante Oral: ¿warfarina o Acenocumarol? Med. Clin. (Barc). 2008, 131 (3), 98–100. | |
dc.relation | (13) Yu, X.; Teng, P.; Zhang, Y.; Xu, Z.; Zhang, M.; Zhang, W. Fitoterapia Design , Synthesis and Antifungal Activity Evaluation of Coumarin-3- Carboxamide Derivatives. Fitoterapia 2018, 127 (March), 387–395. | |
dc.relation | (14) Khomenko, T. M.; Zarubaev, V. V.; Orshanskaya, I. R.; Kadyrova, R. A.; Sannikova, V. A.; Korchagina, D. V.; Volcho, K. P.; Salakhutdinov, N. F. Anti-Influenza Activity of Monoterpene-Containing Substituted Coumarins. Bioorganic Med. Chem. Lett. 2017, 27 (13), 2920–2925. | |
dc.relation | (15) Bizzarri, B. M.; Botta, L.; Capecchi, E.; Celestino, I.; Checconi, P.; Palamara, A. T.; Nencioni, L.; Saladino, R. Regioselective IBX-Mediated Synthesis of Coumarin Derivatives with Antioxidant and Anti-Influenza Activities. J. Nat. Prod. 2017, 80 (12), 3247–3254. | |
dc.relation | (16) Şahin, Ö.; Özdemir, Ü. Ö.; Seferoğlu, N.; Genc, Z. K.; Kaya, K.; Aydıner, B.; Tekin, S.; Seferoğlu, Z. New Platinum (II) and Palladium (II) Complexes of Coumarin-Thiazole Schiff Base with a Fluorescent Chemosensor Properties: Synthesis, Spectroscopic Characterization, X-Ray Structure Determination, in Vitro Anticancer Activity on Various Human Carcinoma Ce. J. Photochem. Photobiol. B Biol. 2018, 178 (November 2017), 428–439. | |
dc.relation | (17) Sun, S.; Phrutivorapongkul, A.; Dibwe, D. F.; Balachandran, C.; Awale, S. Chemical Constituents of Thai Citrus Hystrix and Their Antiausterity Activity against the PANC-1 Human Pancreatic Cancer Cell Line. J. Nat. Prod. 2018, 81 (8), 1877–1883. | |
dc.relation | (18) Hu, Y. Q.; Xu, Z.; Zhang, S.; Wu, X.; Ding, J. W.; Lv, Z. S.; Feng, L. S. Recent Developments of Coumarin-Containing Derivatives and Their Anti-Tubercular Activity. Eur. J. Med. Chem. 2017, 136, 122–130. | |
dc.relation | (19) Najafi, Z.; Mahdavi, M.; Saeedi, M.; Karimpour-Razkenari, E.; Edraki, N.; Sharifzadeh, M.; Khanavi, M.; Akbarzadeh, T. Novel Tacrine-Coumarin Hybrids Linked to 1,2,3-Triazole as Anti-Alzheimer’s Compounds: In Vitro and in Vivo Biological Evaluation and Docking Study. Bioorg. Chem. 2019, 83 (October 2018), 303–316. | |
dc.relation | (20) Oliveira, E.; Nuñez, C.; Rodríguez-González, B.; Capelo, J. L.; Lodeiro, C. Novel Small Stable Gold Nanoparticles Bearing Fluorescent Cysteine-Coumarin Probes as New Metal-Modulated Chemosensors. Inorg. Chem. 2011, 50 (18), 8797–8807. | |
dc.relation | (21) Bayraktutan, T.; Onganer, Y. Spectral-Luminescent Study of Coumarin 35 as Fluorescent “Light-up” Probe for BSA and DNA Monitoring. Dye. Pigment. 2017, 142, 62–68. | |
dc.relation | (22) Zhao, J.; Zhang, D.; Hua, W.; Li, W.; Xu, G.; Gou, S. Anticancer Activity of Bifunctional Organometallic Ru(II) Arene Complexes Containing a 7-Hydroxycoumarin Group. Organometallics 2018, 37 (3), 441–447. | |
dc.relation | (23) Singh, H.; Sreedharan, S.; Tiwari, R.; Walther, C.; Smythe, C.; Pramanik, S. K.; Thomas, J. A.; Das, A. A Fluorescent Chemodosimeter for Organelle-Specific Imaging of Nucleoside Polyphosphate Dynamics in Living Cells. Cryst. Growth Des. 2018, 18 (11), 7199–7206. | |
dc.relation | (24) Yan, L.; Li, R.; Shen, W.; Qi, Z. Multiple–color AIE Coumarin–based Schiff Bases and Potential Application in Yellow OLEDs. J. Lumin. 2018, 194 (January 2017), 151–155. | |
dc.relation | (25) Karami, B.; Kiani, M. ZrOCl2.8H2O/SiO2: An Efficient and Recyclable Catalyst for the Preparation of Coumarin Derivatives by Pechmann Condensation Reaction. Catal. Commun. 2011, 14 (1), 62–67. | |
dc.relation | (26) Prousis, K. C.; Avlonitis, N.; Heropoulos, G. A.; Calogeropoulou, T. FeCl3-Catalysed Ultrasonic-Assisted, Solvent-Free Synthesis of 4-Substituted Coumarins. A Useful Complement to the Pechmann Reaction. Ultrason. Sonochem. 2014, 21 (3), 937–942. | |
dc.relation | (27) Augustine, J. K.; Bombrun, A.; Ramappa, B.; Boodappa, C. An Efficient One-Pot Synthesis of Coumarins Mediated by Propylphosphonic Anhydride (T3P) via the Perkin Condensation. Tetrahedron Lett. 2012, 53 (33), 4422–4425. | |
dc.relation | (28) Patre, R. E.; Shet, J. B.; Parameswaran, P. S.; Tilve, S. G. Cascade Wittig Reaction-Double Claisen and Cope Rearrangements: One-Pot Synthesis of Diprenylated Coumarins Gravelliferone, Balsamiferone, and 6,8-Diprenylumbelliferone. Tetrahedron Lett. 2009, 50 (47), 6488–6490. | |
dc.relation | (29) Ghomi, J. S.; Akbarzadeh, Z. Ultrasonic Accelerated Knoevenagel Condensation by Magnetically Recoverable MgFe2O4nanocatalyst: A Rapid and Green Synthesis of Coumarins under Solvent-Free Conditions. Ultrason. Sonochem. 2018, 40 (April 2017), 78–83. | |
dc.relation | (30) Khan, D.; Mukhtar, S.; Alsharif, M. A.; Alahmdi, M. I.; Ahmed, N. PhI(OAc)2 mediated an Efficient Knoevenagel Reaction and Their Synthetic Application for Coumarin Derivatives. Tetrahedron Lett. 2017, 58 (32), 3183–3187. | |
dc.relation | (31) Matern, U.; Lüer, P.; Kreusch, D. Biosynthesis of Coumarins. Compr. Nat. Prod. Chem. 1999, 1, 623–637. | |
dc.relation | (32) Bhatta, S. R.; Bheemireddy, V.; Thakur, A. A Redox-Driven Fluorescence “Off-On” Molecular Switch Based on a 1,1′-Unsymmetrically Substituted Ferrocenyl Coumarin System: Mimicking Combinational Logic Operation. Organometallics 2017, 36 (4), 829–838. | |
dc.relation | (33) Formica, M.; Fusi, V.; Giorgi, L.; Micheloni, M. New Fluorescent Chemosensors for Metal Ions in Solution. Coord. Chem. Rev. 2012, 256 (1–2), 170–192. | |
dc.relation | (34) Requena, A., Zúñiga, J. Espectroscopía, Pearson/Prentice Hall, 2004,353-358 | |
dc.relation | (35) De Silva, A. P.; Moody, T. S.; Wright, G. D. Fluorescent PET (Photoinduced Electron Transfer) Sensors as Potent Analytical Tools. Analyst 2009, 134 (12), 2385–2393. | |
dc.relation | (36) Escudero, D. Revising Intramolecular Photoinduced Electron Transfer (PET) from First-Principles. Acc. Chem. Res. 2016, 49 (9), 1816–1824. | |
dc.relation | (37) Liu, B.; Bazan, G. C. Optimization of the Molecular Orbital Energies of Conjugated Polymers for Optical Amplification of Fluorescent Sensors. J. Am. Chem. Soc. 2006, 128 (4), 1188–1196. | |
dc.relation | (38) Yanar, U.; Babür, B.; Pekyilmaz, D.; Yahaya, I.; Aydiner, B.; Dede, Y.; Seferoʇlu, Z. A Fluorescent Coumarin-Thiophene Hybrid as a Ratiometric Chemosensor for Anions: Synthesis, Photophysics, Anion Sensing and Orbital Interactions. J. Mol. Struct. 2016, 1108, 269–277. | |
dc.relation | (39) Babür, B.; Seferoğlu, N.; Seferoğlu, Z. A Coumarin-Pyrazolone Based Fluorescent Probe for Selective Colorimetric and Fluorimetric Fluoride Detection: Synthesis, Spectroscopic Properties and DFT Calculations. J. Mol. Struct. 2018, 1161, 218–225. | |
dc.relation | (40) Wu, Q.; Liu, Z.; Cao, D.; Guan, R.; Wang, K.; Shan, Y.; Xu, Y.; Ma, L. Coumarin Amide Derivatives as Fluorescence Chemosensors for Cyanide Anions. Mater. Chem. Phys. 2015, 161, 43–48. | |
dc.relation | (41) Cheng, X.; Tang, R.; Jia, H.; Feng, J.; Qin, J.; Li, Z. New Fluorescent and Colorimetric Probe for Cyanide: Direct Reactivity, High Selectivity, and Bioimaging Application. ACS Appl. Mater. Interfaces 2012, 4 (8), 4387–4392. | |
dc.relation | (42) Meng, X.; Li, S.; Ma, W.; Wang, J.; Hu, Z.; Cao, D. Highly Sensitive and Selective Chemosensor for Cu2+ and H2PO4−based on Coumarin Fluorophore. Dye. Pigment. 2018, 154 (November 2017), 194–198. | |
dc.relation | (43) Tan, W.; Leng, T.; Lai, G.; Li, Z.; Wang, K.; Shen, Y.; Wang, C. A Novel Coumarin-Based Fluorescence Enhancement and Colorimetric Probe for Cu2+ via Selective Hydrolysis Reaction. J. Photochem. Photobiol. A Chem. 2016, 324, 81–86. | |
dc.relation | (44) Mukherjee, S.; Hazra, S.; Chowdhury, S.; Sarkar, S.; Chattopadhyay, K.; Pramanik, A. A Novel Pyrrole Fused Coumarin Based Highly Sensitive and Selective Fluorescence Chemosensor for Detection of Cu2+ ions and Applications towards Live Cell Imaging. J. Photochem. Photobiol. A Chem. 2018, 364 (May), 635–644. | |
dc.relation | (45) Lim, D. S.; Park, S. Y.; Hwang, K. S.; Chang, S. K. Colorimetric Determination of Hg2+ via Thiosemicarbazide-to-Oxadiazole Transformation of a Coumarin-Benzopyrylium Dye. Tetrahedron Lett. 2018, 59 (19), 1819–1822. | |
dc.relation | (46) Yan, Z.; Yuen, M. F.; Hu, L.; Sun, P.; Lee, C. S. Advances for the Colorimetric Detection of Hg2+ in Aqueous Solution. RSC Adv. 2014, 4 (89), 48373–48388. | |
dc.relation | (47) Wu, C.; Wang, J.; Shen, J.; Bi, C.; Zhou, H. Coumarin-Based Hg2+ fluorescent Probe: Synthesis and Turn-on Fluorescence Detection in Neat Aqueous Solution. Sensors Actuators, B Chem. 2017, 243, 678–683. | |
dc.relation | (48) Warrier, S.; Kharkar, P. S. Highly Selective On-off Fluorescence Recognition of Fe3+based on a Coumarin Derivative and Its Application in Live-Cell Imaging. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 2018, 188, 659–665. | |
dc.relation | (49) Li, Z.; Zhou, Y.; Yin, K.; Yu, Z.; Li, Y.; Ren, J. A New Fluorescence “Turn-on” Type Chemosensor for Fe3+ based on Naphthalimide and Coumarin. Dye. Pigment. 2014, 105, 7–11. | |
dc.relation | (50) Yao, J.; Dou, W.; Qin, W.; Liu, W. A New Coumarin-Based Chemosensor for Fe3+ in Water. Inorg. Chem. Commun. 2009, 12 (2), 116–118. | |
dc.relation | (51) An, J. M.; Yan, M. H.; Yang, Z. Y.; Li, T. R.; Zhou, Q. X. A Turn-on Fluorescent Sensor for Zn(II) Based on Fluorescein-Coumarin Conjugate. Dye. Pigment. 2013, 99 (1), 1–5. | |
dc.relation | (52) Gao, Y.; Liu, H.; Li, P.; Liu, Q.; Wang, W.; Zhao, B. Coumarin-Based Fluorescent Chemosensor for the Selective Quantification of Zn2+and AcO−in an Aqueous Solution and Living Cells. Tetrahedron Lett. 2017, 58 (23), 2193–2198. | |
dc.relation | (53) Zhu, Q.; Li, L.; Mu, L.; Zeng, X.; Redshaw, C.; Wei, G. A Ratiometric Al3+ ion Probe Based on the Coumarin-Quinoline FRET System. J. Photochem. Photobiol. A Chem. 2016, 328, 217–224. | |
dc.relation | (54) Yang, L.; Wang, C.; Chang, G.; Ren, X. Facile Synthesis of New Coumarin-Based Colorimetric and Fluorescent Chemosensors: Highly Efficient and Selective Detection of Pd2+in Aqueous Solutions. Sensors Actuators, B Chem. 2017, 240, 212–219. | |
dc.relation | (55) Liu, Z.; Wang, W.; Xu, H.; Sheng, L.; Chen, S.; Huang, D.; Sun, F. A “Naked Eye” and Ratiometric Chemosensor for Cobalt(II) Based on Coumarin Platform in Aqueous Solution. Inorg. Chem. Commun. 2015, 62, 19–23. | |
dc.relation | (56) Jiang, J.; Gou, C.; Luo, J.; Yi, C.; Liu, X. A Novel Highly Selective Colorimetric Sensor for Ni(II) Ion Using Coumarin Derivatives. Inorg. Chem. Commun. 2012, 15, 12–15. | |
dc.relation | (57) Xu, J.; Zheng, W.; Huang, X.; Cheng, Y.; Shen, P. Selective Fluorescent Probe Based on Schiff Base Derived from Hydroxymethyl Coumarin and Aminated Sudan I Dye for Mg2+ detection. Arab. J. Chem. 2017, 10, 2729–2735. | |
dc.relation | (58) Ezeh, V. C.; Harrop, T. C. A Sensitive and Selective Fluorescence Sensor for the Detection of Arsenic(III) in Organic Media. Inorg. Chem. 2012, 51 (3), 1213–1215. | |
dc.relation | (59) Tang, Y.; Li, Y.; Han, J.; Mao, Y.; Ni, L.; Wang, Y. A Coumarin Based Fluorescent Probe for Rapidly Distinguishing of Hypochlorite and Copper (II) Ion in Organisms. Spectrochim. Acta - Part A Mol. Biomol. Spectrosc. 2019, 208, 299–308. | |
dc.relation | (60) Pang, B. jie; Li, Q.; Li, C. rui; Yang, Z. yin. A Highly Selective and Sensitive Coumarin Derived Fluorescent Probe for Detecting Hg2+ in 100% Aqueous Solutions. J. Lumin. 2019, 205 (September 2018), 446–450. | |
dc.relation | (61) Li, Q.; Hu, Y.; Hou, H. N.; Yang, W. N.; Hu, S. L. A New Coumarin-Carbonothioate-Based Turn-on Fluorescent Chemodosimeter for Selective Detection of Hg2+. Inorganica Chim. Acta 2018, 471, 705–708. | |
dc.relation | (62) Huang, K.; Jiao, X.; Liu, C.; Wang, Q.; Qiu, X.; Zheng, D.; He, S.; Zhao, L.; Zeng, X. Highly Selective and Sensitive Fluorescent Probe for Mercury Ions Based on a Novel Rhodol-Coumarin Hybrid Dye. Dye. Pigment. 2017, 142, 437–446. | |
dc.relation | (63) Shaily; Kumar, A.; Ahmed, N. Indirect Approach for CN-Detection: Development of “Naked-Eye” Hg2+ Induced Turn-Off Fluorescence and Turn-On Cyanide Sensing by the Hg2+Displacement Approach. Ind. Eng. Chem. Res. 2017, 56 (22), 6358–6368. | |
dc.rights | Reconocimiento 4.0 Internacional | |
dc.rights | http://creativecommons.org/licenses/by/4.0/ | |
dc.rights | info:eu-repo/semantics/openAccess | |
dc.title | Síntesis y caracterización de derivados cumarín piridínicos y su aplicación en la detección de un ion metálico | |
dc.type | Trabajo de grado - Maestría | |