2018 |
Cassels, B K; Saez-Briones, P Dark Classics in Chemical Neuroscience: Mescaline Artículo de revista Acs Chemical Neuroscience, 9 (10), pp. 2448-2458, 2018, ISSN: 1948-7193. Resumen | Enlaces | BibTeX | Etiquetas: analogs, biosynthesis, cancer, derivatives, diethylamide, hallucinogen, hallucinogenic life-threatening lysergic-acid mescaline, metabolism, pedro, peyote, pharmacology, phenethylamine, phenyl-aethylamine, properties, relationships, san serotonin stimulus structure-activity synthesis, wachuma @article{RN389, title = {Dark Classics in Chemical Neuroscience: Mescaline}, author = { B.K. Cassels and P. Saez-Briones}, url = {/brokenurl#<Go to ISI>://WOS:000447954300015}, doi = {10.1021/acschemneuro.8b00215}, issn = {1948-7193}, year = {2018}, date = {2018-01-01}, journal = {Acs Chemical Neuroscience}, volume = {9}, number = {10}, pages = {2448-2458}, abstract = {Archeological studies in the United States, Mexico, and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote (Lophophora williamsii) and the South American wachuma (Trichocereus pachanoi, T. peruvianus, and T. bridgesii). Spanish 16th century chroniclers considered these cacti "diabolic", leading to their prohibition, but their use persisted to our days and has been spreading for the last 150 years. In the late 1800s, peyote attracted scientific attention; mescaline was isolated, and its role in the psychedelic effects of peyote tops or "mescal buttons" was demonstrated. Its structure was established by synthesis in 1929, and alternative routes were developed, providing larger amounts for pharmacological and biosynthetic research. Although its effects are attributed mainly to its action as a 5-HT2A serotonin receptor agonist, mescaline binds in a similar concentration range to 5-HT1A and alpha(2A) receptors. It is largely excreted unchanged in human urine, and its metabolic products are apparently unrelated to its psychedelic properties. Its low potency is probably responsible for its relative neglect by recreational substance users, as the successful search for structure-activity relationships in the hallucinogen field focused largely on finding more potent analogues. Renewed interest in the possible therapeutic applications of psychedelic drugs may hopefully lead to novel insights regarding the commonalities and differences between the actions of individual classic hallucinogens.}, keywords = {analogs, biosynthesis, cancer, derivatives, diethylamide, hallucinogen, hallucinogenic life-threatening lysergic-acid mescaline, metabolism, pedro, peyote, pharmacology, phenethylamine, phenyl-aethylamine, properties, relationships, san serotonin stimulus structure-activity synthesis, wachuma}, pubstate = {published}, tppubtype = {article} } Archeological studies in the United States, Mexico, and Peru suggest that mescaline, as a cactus constituent, has been used for more than 6000 years. Although it is a widespread cactus alkaloid, it is present in high concentrations in few species, notably the North American peyote (Lophophora williamsii) and the South American wachuma (Trichocereus pachanoi, T. peruvianus, and T. bridgesii). Spanish 16th century chroniclers considered these cacti "diabolic", leading to their prohibition, but their use persisted to our days and has been spreading for the last 150 years. In the late 1800s, peyote attracted scientific attention; mescaline was isolated, and its role in the psychedelic effects of peyote tops or "mescal buttons" was demonstrated. Its structure was established by synthesis in 1929, and alternative routes were developed, providing larger amounts for pharmacological and biosynthetic research. Although its effects are attributed mainly to its action as a 5-HT2A serotonin receptor agonist, mescaline binds in a similar concentration range to 5-HT1A and alpha(2A) receptors. It is largely excreted unchanged in human urine, and its metabolic products are apparently unrelated to its psychedelic properties. Its low potency is probably responsible for its relative neglect by recreational substance users, as the successful search for structure-activity relationships in the hallucinogen field focused largely on finding more potent analogues. Renewed interest in the possible therapeutic applications of psychedelic drugs may hopefully lead to novel insights regarding the commonalities and differences between the actions of individual classic hallucinogens. |
2015 |
Costantino, A R; Schneider, M G M; Galdamez, A; Ocampo, R A; Mandolesi, S D; Koll, L C The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement Artículo de revista Tetrahedron-Asymmetry, 26 (23), pp. 1341-1347, 2015, ISSN: 0957-4166. Resumen | Enlaces | BibTeX | Etiquetas: analogs, anhydrides carboxylic-acids, derivatives, esterification, esters, in-situ, inhibitors, integrase ligands, taddol @article{RN258, title = {The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement}, author = { A.R. Costantino and M.G.M. Schneider and A. Galdamez and R.A. Ocampo and S.D. Mandolesi and L.C. Koll}, url = {/brokenurl#<Go to ISI>://WOS:000366070000005}, doi = {10.1016/j.tetasy.2015.10.014}, issn = {0957-4166}, year = {2015}, date = {2015-01-01}, journal = {Tetrahedron-Asymmetry}, volume = {26}, number = {23}, pages = {1341-1347}, publisher = {2015 Elsevier Ltd.}, abstract = {An efficient, green, and atom economic methodology for the stereoselective synthesis of C-2 symmetry (3R,4R)-TTFOL diester derivatives has been developed. The procedure occurs through a (2R,3R)-TADDOL dioxolane cleavage and rearrangement under mild conditions by its reaction with a carboxylic acid in the presence of TFAA/H3PO4 without the need for an inert atmosphere to give generally high yields.}, keywords = {analogs, anhydrides carboxylic-acids, derivatives, esterification, esters, in-situ, inhibitors, integrase ligands, taddol}, pubstate = {published}, tppubtype = {article} } An efficient, green, and atom economic methodology for the stereoselective synthesis of C-2 symmetry (3R,4R)-TTFOL diester derivatives has been developed. The procedure occurs through a (2R,3R)-TADDOL dioxolane cleavage and rearrangement under mild conditions by its reaction with a carboxylic acid in the presence of TFAA/H3PO4 without the need for an inert atmosphere to give generally high yields. |
Martinez-Cifuentes, M; Weiss-Lopez, B; Santos, L S; Araya-Maturana, R Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1663-1672, 2015, ISSN: 1568-0266. Resumen | Enlaces | BibTeX | Etiquetas: alzheimer, analogs, antibacterial, antiinflammatory antioxidant, antioxidants, apoptosis, bioavailability, cancer, curcumin, cytotoxicity, heterocycles, in-vitro, inhibitors molecular properties, targets @article{RN266, title = {Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress}, author = { M. Martinez-Cifuentes and B. Weiss-Lopez and L.S. Santos and R. Araya-Maturana}, url = {/brokenurl#<Go to ISI>://WOS:000355570800003}, doi = {10.2174/1568026615666150427111837}, issn = {1568-0266}, year = {2015}, date = {2015-01-01}, journal = {Current Topics in Medicinal Chemistry}, volume = {15}, number = {17}, pages = {1663-1672}, abstract = {Curcumin, a natural yellow polyphenol, is isolated from the herb Curcuma longa L. (turmeric), a member of the ginger family. It has been extensively studied due to their multiple pharmacological properties. Nevertheless, curcumin has disadvantages such as poor water solubility, poor bioavailability and rapid metabolism, which has prompted the search for analogues that overcome these shortcomings while maintaining or improving their good pharmacological properties. Among the main curcumin analogues that have been developed, the heterocyclic curcuminoids show a high interest. In this review, we describe recent progress in the synthesis and pharmacological properties of new heterocyclic curcumin derivatives. The most recent developments in anti-cancer, anti-Alzheimer, anti-bacterial and anti-oxidants heterocyclic curcumin derivatives are covered.}, keywords = {alzheimer, analogs, antibacterial, antiinflammatory antioxidant, antioxidants, apoptosis, bioavailability, cancer, curcumin, cytotoxicity, heterocycles, in-vitro, inhibitors molecular properties, targets}, pubstate = {published}, tppubtype = {article} } Curcumin, a natural yellow polyphenol, is isolated from the herb Curcuma longa L. (turmeric), a member of the ginger family. It has been extensively studied due to their multiple pharmacological properties. Nevertheless, curcumin has disadvantages such as poor water solubility, poor bioavailability and rapid metabolism, which has prompted the search for analogues that overcome these shortcomings while maintaining or improving their good pharmacological properties. Among the main curcumin analogues that have been developed, the heterocyclic curcuminoids show a high interest. In this review, we describe recent progress in the synthesis and pharmacological properties of new heterocyclic curcumin derivatives. The most recent developments in anti-cancer, anti-Alzheimer, anti-bacterial and anti-oxidants heterocyclic curcumin derivatives are covered. |
2013 |
Mella-Raipan, J A; Lagos, C F; Recabarren-Gajardo, G; Espinosa-Bustos, C; Romero-Parra, J; Pessoa-Mahana, H; Iturriaga-Vasquez, P; Pessoa-Mahana, C D Design, Synthesis, Binding and Docking-Based 3d-Qsar Studies of 2-Pyridylbenzimidazoles-a New Family of High Affinity Cb1 Cannabinoid Ligands Artículo de revista Molecules, 18 (4), pp. 3972-4001, 2013, ISSN: 1420-3049. Resumen | Enlaces | BibTeX | Etiquetas: agonists, analogs, analysis, binding, cannabinoid, cb1 comfa derivatives, docking, molecular-field pharmacology, protease receptor, series, system @article{RN128, title = {Design, Synthesis, Binding and Docking-Based 3d-Qsar Studies of 2-Pyridylbenzimidazoles-a New Family of High Affinity Cb1 Cannabinoid Ligands}, author = { J.A. Mella-Raipan and C.F. Lagos and G. Recabarren-Gajardo and C. Espinosa-Bustos and J. Romero-Parra and H. Pessoa-Mahana and P. Iturriaga-Vasquez and C.D. Pessoa-Mahana}, url = {/brokenurl#<Go to ISI>://WOS:000318020100024}, doi = {10.3390/molecules18043972}, issn = {1420-3049}, year = {2013}, date = {2013-01-01}, journal = {Molecules}, volume = {18}, number = {4}, pages = {3972-4001}, abstract = {A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with K-i values in the nanomolar range. JM-39 (compound 39) was the most active of the series (K-iCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q(2) = 0.710, r(2) = 0.998, r(pred)(2) = 0.823).}, keywords = {agonists, analogs, analysis, binding, cannabinoid, cb1 comfa derivatives, docking, molecular-field pharmacology, protease receptor, series, system}, pubstate = {published}, tppubtype = {article} } A series of novel 2-pyridylbenzimidazole derivatives was rationally designed and synthesized based on our previous studies on benzimidazole 14, a CB1 agonist used as a template for optimization. In the present series, 21 compounds displayed high affinities with K-i values in the nanomolar range. JM-39 (compound 39) was the most active of the series (K-iCB1 = 0.53 nM), while compounds 31 and 44 exhibited similar affinities to WIN 55212-2. CoMFA analysis was performed based on the biological data obtained and resulted in a statistically significant CoMFA model with high predictive value (q(2) = 0.710, r(2) = 0.998, r(pred)(2) = 0.823). |
2018 |
Dark Classics in Chemical Neuroscience: Mescaline Artículo de revista Acs Chemical Neuroscience, 9 (10), pp. 2448-2458, 2018, ISSN: 1948-7193. |
2015 |
The Synthesis of C-2 Symmetry Diesters of (3r,4r)-Ttfol through a Green and Stereoselective (2r,3r)-Taddol Rearrangement Artículo de revista Tetrahedron-Asymmetry, 26 (23), pp. 1341-1347, 2015, ISSN: 0957-4166. |
Heterocyclic Curcumin Derivatives of Pharmacological Interest: Recent Progress Artículo de revista Current Topics in Medicinal Chemistry, 15 (17), pp. 1663-1672, 2015, ISSN: 1568-0266. |
2013 |
Design, Synthesis, Binding and Docking-Based 3d-Qsar Studies of 2-Pyridylbenzimidazoles-a New Family of High Affinity Cb1 Cannabinoid Ligands Artículo de revista Molecules, 18 (4), pp. 3972-4001, 2013, ISSN: 1420-3049. |