Las chalconas y su uso como precursores en la síntesis de compuestos heterocíclicos nitrogenados

Braulio Insuasty- Obando

doi:10.18257/raccefyn.309

Vol. 40 No. 155 (2016), Chemical Sciences

Vol. 40 No. 155 (2016)

Chalcones and their use as precursors in the synthesis of nitrogen-containing heterocyclic compounds

Chemical Sciences

https://doi.org/10.18257/raccefyn.309

Published 2016-07-03

Braulio Insuasty- Obando⁺⁻

Braulio Insuasty- Obando

Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad del Valle, Cali, Colombia

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Insuasty- Obando, B. (2016). Chalcones and their use as precursors in the synthesis of nitrogen-containing heterocyclic compounds. Revista De La Academia Colombiana De Ciencias Exactas, Físicas Y Naturales, 40(155), 234–243. https://doi.org/10.18257/raccefyn.309

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Abstract

The synthesis of new compounds with potential biological activity is a major challenge for research in organic and medicinal and is of great impact due to the potential development of new therapies for the treatment of various types of diseases. This document is a summary of the research conducted by Professor Braulio Insuasty Obando and his group in recent years in the topic of synthesis of 5, 6 and 7 members nitrogen-containing heterocyclic compounds (pyrazolines, pyridines and diazepines) with potential biological activity starting from 1,3-diphenyl-2-propen-1-ones (chalcones) and its analogues. The preparation and characterization of the new compounds was conducted in the Grupo de Investigación de Compuestos Heterocíclicos of the Universidad del Valle. To carry out the synthesis reactions, besides conventional energy sources (refluxing) unconventional sources were used such as microwave irradiation and ultrasound. Some reactions were carried out using environmental friendly methods as solvent-free reactions and multicomponent reactions. Use of these synthetic methodologies allows making cleaner reactions, in less time and with better yields. The synthesized compounds were characterized using spectroscopic techniques such as FT-IR, 1D and 2D NMR, mass spectrometry, elemental analysis and X-ray diffraction in some cases. © 2016. Acad. Colomb. Cienc. Ex. Fis. Nat. All rights reserved.

https://doi.org/10.18257/raccefyn.309

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References

Anand, P., Singh, B. (2014). Pyrrolo-isoxazole: A Key Molecule with Diverse Biological Actions. Mini-Reviews in Medicinal Chemistry, 14 (7): 623-627.

Awad, W., El-Neweihy, M., Selim, F. (1960). Studies on 3-Acylcatechols. II. A New Synthesis of 8-Hydroxyflavone. The Journal of Organic Chemistry, 25 (8): 1333-1336.

Insuasty, B., Ramírez, J., Becerra, D., Echeverry, C., Quiroga, J., Abonia, R., Robledo, S. M., Vélez, I. D., Upegui, Y., Muñoz, J. A., Ospina, V., Nogueras, M., Cobo, J. (2015). An efficient synthesis of new caffeine-based chalcones, pyrazolines and pyrazolo[3,4-b][1,4]diazepines as potential antimalarial, antitrypanosomal and antileishmanial agents. European Journal of Medicinal Chemistry, 93: 401-413.

Insuasty, B., Orozco, F., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2014). Synthesis and Structure Elucidation of New Regioisomeric 2-Alkylamino-6-aryl-8,9-dihydropyrimido [4,5-b][1,4]diazepin-4(7H)-ones. Journal of Heterocyclic Chemistry, 51 (1): 196-202.

Insuasty, B., Montoya, A., Becerra, D., Quiroga, J., Abonia, R., Robledo, S., Vélez, I. D., Upegui, Y., Nogueras, M., Cobo, J. (2013a). Synthesis of novel analogs of 2-pyrazoline obtained from [(7-chloroquinolin-4-yl)amino]chalcones and hydrazine as potential antitumor and antimalarial agents. European Journal of Medicinal Chemistry, 67: 252-262.

Insuasty, A., Ramírez, J., Raimondi, M., Echeverry, C., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J., Rodríguez, M. V., Zacchino, S. A., Insuasty, B. (2013b). Synthesis, Antifungal and Antitumor Activity of Novel (Z)-5-Hetarylmethylidene- 1,3-thiazol-4-ones and (Z)-5-Ethylidene-1,3-thiazol-4-ones. Molecules, 18 (5): 5482-5497.

Insuasty, B., Becerra, D., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2013c). Microwave-assisted synthesis of pyrimido[4,5-b][1,6] naphthyridin-4(3H)-ones with potential antitumor activity. European Journal of Medicinal Chemistry, 60: 1-9.

Insuasty, B., Chamizo, L., Muñoz, J., Tigreros, A., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2012a). Synthesis of 1-Substituted 3-Aryl-5-aryl(hetaryl)-2-pyrazolines and Study of Their Antitumor Activity. Archiv der Pharmazie, 345 (4): 275-286.

Insuasty, B., García, A., Bueno, J., Quiroga, J., Abonia, R., Ortiz, A. (2012b). Antimycobacterial Activity of Pyrimido[4,5-b] diazepine Derivatives. Archiv der Pharmazie, 345 (9): 739-744.

Insuasty, B., García, A., Quiroga, J., Abonia, R., Ortiz, A., Nogueras, M., Cobo, J. (2011). Efficient microwaveassisted synthesis and antitumor activity of novel 4,4′-methylenebis[2-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl) phenols]. European Journal of Medicinal Chemistry, 46 (6): 2436-2440.

Insuasty, B., Tigreros, A., Orozco, F., Quiroga, J., Abonia, R., Nogueras, M., Sanchez, A., Cobo, J. (2010a). Synthesis of novel pyrazolic analogues of chalcones and their 3-aryl-4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-1-phenyl-1H-pyrazole derivatives as potential antitumor agents. Bioorganic & Medicinal Chemistry, 18 (14): 4965-4974.

Insuasty, B., García, A., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2010b). Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4]diazepines under microwave irradiation as potential anti-tumor agents. European Journal of Medicinal Chemistry, 45 (7): 2841- 2846.

Insuasty, B., Martinez, H., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2008a). Synthesis of new bis-3,5-diphenylpyrazolines derivatives linked with alkyl chains. Journal of Heterocyclic Chemistry, 45 (5): 1521-1524.

Insuasty, B., Orozco, F., García, A., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2008b). Microwave-assisted synthesis of new regioisomeric 6,7-dihydroindeno[1,2-e] pyrimido[4,5-b][1,4]diazepin-5(5aH)-ones. Journal of Heterocyclic Chemistry, 45 (6): 1659-1663.

Insuasty, B., Orozco, F., Lizarazo, C., Quiroga, J., Abonia, R., Hursthouse, M., Nogueras, M., Cobo, J. (2008c). Synthesis of new indeno[1,2-e] pyrimido[4,5-b][1,4] diazepine-5,11-diones as potential antitumor agents. Bioorganic & Medicinal Chemistry, 16 (18): 8492-8500.

Insuasty, B., Orozco, F., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J. (2008d). Microwave induced synthesis of novel 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as potential antitumor agents. European Journal of Medicinal Chemistry, 43 (9): 1955-1962.

Insuasty, B., Abonia, R., Quiroga, J. (1992). The reaction of ketones with ortho-diamines. I. The reaction of aromatic α,β-unsaturated ketones with 4,5-dimethyl-1,2- phenylenediamine. An. Quim., 88: 718-721.

Kostanecki, S., Tambor, J. (1899). Ueber die sechs isomeren Monooxybenzalacetophenone (Monooxychalkone). Berichte der deutschen chemischen Gesellschaft, 32 (2): 1921-1926.

Mohamed, R., Abdelrahman, S., Ahmad, M. (2012). Recent advances in the therapeutic applications of pyrazolines. Expert Opinion on Therapeutic Patents, 22 (3): 253-291.

Montoya, A., Quiroga, J., Abonia, R., Nogueras, M., Cobo, J., Insuasty, B. (2014). Synthesis and in Vitro Antitumor Activity of a Novel Series of 2-Pyrazoline Derivatives Bearing the 4-Aryloxy-7-chloroquinoline Fragment. Molecules, 19 (11): 18656-18675.

Parvesh, S., Amit, A., Vipan, K. (2014). Recent developments in biological activities of chalcones: A mini review. European Journal of Medicinal Chemistry, 85: 758-777.

Quiroga, J., Insuasty, B., Rincón, R., Larrahondo, M., Hanold, N., Meier, H. (1994). The formation of pyrazolo[1,5-a] pyrimidines by the reaction of 3-(4-chlorophenyl) pyrazol-5-amine with chalcones. Journal of Heterocyclic Chemistry, 31 (6): 1333-1335.

Ramajayam, R., Girdhar, R., Yadav, M. (2007). Current Scenario of 1,4-Diazepines as Potent Biomolecules-A Mini Review. Mini-Reviews in Medicinal Chemistry, 7 (8): 793-812.

Ramírez, J., Svetaz, L., Quiroga, J., Abonia, R., Raimondi, M., Zacchino, S., Insuasty, B. (2015). Synthesis of novel thiazole-based 8,9-dihydro-7H-pyrimido[4,5-b][1,4] diazepines as potential antitumor and antifungal agents. European Journal of Medicinal Chemistry, 92: 866-875.

Ramírez, J., Rodríguez, M. V., Quiroga, J., Abonia, R., Sortino, M., Zacchino, S. A., Insuasty, B. (2014). Efficient Synthesis of Novel 3-Aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and Their Antifungal Activity Alone and in Combination with Commercial Antifungal Agents. Archiv der Pharmazie, 347 (8): 566-575.

Sortino, M., Delgado, P., Juárez, S., Quiroga, J., Abonia, R., Insuasty, B., Nogueras, M., Rodero, L., Garibottoe, F. M., Enrize, R. D., Zacchino, S. (2007). Synthesis and antifungal activity of (Z)-5-arylidenerhodanines.

Bioorganic & Medicinal Chemistry, 15 (1): 484-494.

Vianna-Rodrigues, S., Martins-Viana, L., Quiroga, J., Insuasty, B., Abonia, R., Baumann, W. (1994). Chromatographic and spectroscopic properties of regioisomers of some 1H-1,5-benzodiazepines. Journal of Heterocyclic Chemistry, 31 (4): 813-817.

Wenglowsky, S. (2013). Pyrazolo[3,4-b]pyridine kinase inhibitors: a patent review (2008 - present). Expert Opinion on Therapeutic Patents, 23 (3): 281-298.

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