PATENTES OTORGADAS

1.       Nuevos Compuestos Análogos de la Anfotericina y Composiciones Farmacéuticas que lo contienen.

Armando Antillón Díaz, Mauricio Carrillo Tripp, Mario Fernández Zertuche, José David Flores Romero, Fabiola Eloisa Jiménez Montejo, Ángel León Buitimea, Rosmarbel Morales Nava, Lilia Ocampo Martínez, Iván Ortega Blake, Jorge Alberto Reyes Esparza, María de Lourdes Rodríguez Fragoso, Tania Minerva Santiago Angelino, María Cristina Vargas Espinoza. No. de Solicitud: Mx/a/2010/014422. Fecha de Solicitud 21/12/2010. Fecha Otorgada: 21/05/2019. Título de la Patente No. 365148

ARTÍCULOS EN REVISTAS INDEXADAS

2021

37. I. Ortega‐Blake V., Fernández‐Zertuche M., Regla I., Sánchez‐Peña W., Gómez‐Solis A., Jaimes‐Chavez P., A. Galván‐Hernández P., E. Tovar‐Garduño P., Rodríguez‐Fragoso L.*, Preclinical safety evaluation of amphotericin A21: A novel antifungal, Basic Clin. Pharmacol. Toxicol. (2021) bcpt.13592. https://doi.org/10.1111/bcpt.13592

2020

36. Díaz‐Peralta, L.; Razo‐Hernández, R. S.; Pastor, N.; Santiago, Á.; Guevara‐Salazar, J. A.; Fernández‐Zertuche, M.* 1,4‐Disubstituted‐1,2,3‐triazole GABA Analogues: Synthesis, In Vitro Evaluation, Quantum QSAR and Molecular Docking against Pseudomonas Fluorescens GABA‐AT. ChemistrySelect 2020, 5 (3), 1071–1079 DOI: 10.1002/slct.201901485

2019

35. Martínez‐Campos, Z.; Pastor, N.; Pineda‐Urbina, K.; Gómez‐Sandoval, Z.; Fernández‐Zertuche, M.*; Razo‐Hernández, R. S.* In Silico Structure‐based Design of <scp> GABA B </Scp> Receptor Agonists Using a Combination of Docking and <scp>QSAR</Scp>. Chem. Biol. Drug Des. 2019, cbdd.13580 DOI: 10.1111/cbdd.13580

2018

34. Rodríguez-Lozada, J.; Tovar-Gudiño, E.; Guevara-Salazar, J.; Razo-Hernández, R.; Santiago, Á.; Pastor, N.; Fernández-Zertuche, M.* QSAR and Molecular Docking Studies of the Inhibitory Activity of Novel Heterocyclic GABA Analogues over GABA-AT. Molecules 2018, 23 (11), 2984. DOI: 10.3390/molecules23112984

33. Tovar-Gudiño, E.; Guevara-Salazar, J.; Bahena-Herrera, J.; Trujillo-Ferrara, J.; Martínez-Campos, Z.; Razo-Hernández, R.; Santiago, Á.; Pastor, N.; Fernández-Zertuche, M.* Novel-Substituted Heterocyclic GABA Analogues. Enzymatic Activity against the GABA-AT Enzyme from Pseudomonas Fluorescens and In Silico Molecular Modeling. Molecules 2018, 23 (5), 1128. DOI: 10.3390/molecules23051128

2016

 32. Flores-Romero, J. D.; Rodríguez-Lozada, J.; López-Ortiz, M.; Magaña, R.; Ortega-Blake, I.; Regla, I.*; Fernández-Zertuche, M.* Multigram Scale Synthesis of A21, A New Antibiotic Equally Effective and Less Toxic than Amphotericin B. Org. Process Res. Dev. 2016, 20 (8), 1529–1532. DOI: 10.1021/acs.oprd.6b00211

31. Antillón, A.; de Vries, A. H.; Espinosa-Caballero, M.; Falcón-González, J. M.; Romero, D. F.; González–Damián, J.; Jiménez-Montejo, F. E.; León-Buitimea, A.; López-Ortiz, M.; Magaña, R.; Marrink Siewert J.; Morales-Nava R.; Periole X.; Reyes-Esparza J.; Rodríguez Lozada J.; Santiago-Angelino T.; Vargas González M.; Regla I.; Carrillo-Tripp M.; Feranández-Zertuche M.; Rodríguez-Fragoso L.; Ortega- Blake I.;* An Amphotericin B Derivative Equally Potent to Amphotericin B and with Increased Safety. PLoS One 2016, 11 (9), e0162171. DOI: 10.1371/journal.pone.0162171

30. de la Cruz-Cordero, R.; Labastida-Galván, V.; Fernández-Zertuche, M.; Ordóñez, M.* Preparation of Phosphostatine Analogues From L-Amino Acids. 2016. Online

29. Loredo-Calderón, E. L.; López-Cortina, S. T.*; Carranza-Rosales, P.; Viveros-Valdez, E.; Hernández-Fernández, E.; Fernández-Zertuche, M. Synthesis and Characterization of Six Nonsymmetric A3B Porphyrins with P-Chlorophenyl as Meso-Substituent A or B and Determination of Their Photodynamic Activity. Med. Chem. Res. 1–9. DOI: 10.1007/s00044-016-1600-4

2014

28. Morales-Nava, R.; Ramírez-Solís, A.; Fernández-Zertuche, M.* NMR and Theoretical Studies on the Conformational Preferences of Some Non-Metal Coordinated N-Enoyl Systems Attached to Common Chiral Auxilaries. J. Mex. Chem. Soc. 2014, 58 (2), 89–94. Online 

27. Rodriguez-Lopez, A.; Ortega, I.; Fernandez-Zertuche, M.; Regla, I.; Reyes-Esparza, J.; Rodríguez-Fragoso, L. Evaluation of Safety and Efficacy Antifungal of an Amide Derivative of Amphotericin B as Scaling Product on in Vitro Models (844.12). FASEB J. 2014, 28 (1 Supplement), 812–844. Online

2013

26. Tovar-Gudiño, E.; Morales-Nava, R.; Fernández-Zertuche, M.* Diasteroselective Conjugate Addition of Diethylaluminum Cyanide to a Conjugated N-Enoyl System: An Alternative Synthesis of (S)-Pregabalin. Can. J. Chem. 2013, 92 (1), 45–48. DOI: 10.1139/cjc-2013-0397

2011

25. López Cortina, S.*; Elizondo Martínez, P.; Pérez Rodríguez, N.; Hernández Fernández, E.; Fernández Zertuche, M. Synthesis of 3-OXO-3-Phenyl-2, 2, 5-Trimethyl-1, 3-Oxaphosphorinanes and Their Tetrafluoroborate Salts. Química Hoy 2011, 1 (2), 2–9. Online 

24. Balbás, I. M.; Mendoza, B. E. D.; Fernández-Zertuche, M.; Ordoñez, M.; Linzaga-Elizalde, I.* Synthesis of Cis-and Trans-3-Aminocyclohexanols by Reduction of β-Enaminoketones. Molecules 2012, 17 (1), 151–162. DOI: 10.3390/molecules17010151

23. Morales-Nava, R.; Fernández-Zertuche, M.*; Ordóñez, M. Microwave-Assisted Improved Synthesis of Oxazolidin-2-Ones, Oxazolidine-2-Thiones and Thiazolidine-2-Thione Chiral Auxiliaries. Molecules 2011, 16 (10), 8803–8814. DOI: 10.3390/molecules16108803

2010

22. León-Buitimea, A.; Morales-Nava, R.; Fernández-Zertuche, M.; Ortega-Blake, I.; Reyes-Esparza, J.; Rodriguez-Fragoso, L. Pharmacological and Toxicological Study of Two Analogues of Amphotericin by Using in Vitro Models. FASEB J. 2010, 24 (1 Supplement), 961–964. Online 

21.López-Cortina, S.; Medina-Arreguin, A.; Hernández-Fernández, E.; Bernès, S.; Guerrero-Alvarez, J.; Ordoñez, M.; Fernández-Zertuche, M.* Stereochemistry of Base-Induced Cleavage of Methoxide Ion on Cis-and Trans-1, 4-Diphenylphosphorinanium Salts. A Different Behavior with a Phenyl Substituent. Tetrahedron 2010, 66 (32), 6188–6194. DOI: 10.1016/j.tet.2010.05.095

2007

20. Poo, J. L.*; Gongora, J.; Sanchez-Avila, J. F.; Aguilar-Castillo, S.; Ramos, G. G.; Fernandez-Zertuche, M.; Rodriguez-Fragoso, L.; Uribe, M. [81] Efficacy and safety of l-ornithine-l-aspartate (lola) administration. open label randomized controlled trial versus lactulose in cirrhotic patients with hyperammonemic hepatic encephalopathy. J. Hepatol. 2007, 46, S36. DOI: 10.1016/S0168-8278(07)61679-1

19.Rojas-Cabrera, H.; Ochoa-Morales, J.; Hernández-Núñez, E.; Fernández Zertuche, M.; Ordóñez, M.* Efficient and Practical Synthesis of Syn-and Anti-Β, Υ-Dihydroxyphosphonates Derived from (S)-Mandelic Acid. J. Mex. Chem. Soc. 2007, 51 (4), 237–244. Online

18.Rojas-Cabrera, H.; Fernández-Zertuche, M.; García-Barradas, O.; Muñoz-Muñiz, O.; Ordóñez, M.* Preparation of Dimethyl (R)-and (S)-2-(2-Hydroxyphenyl)-2-Hydroxyethylphosphonate Derived from Salicylaldehyde via Resolution Using (S)-Methoxyphenylacetic Acid (MPA). Tetrahedron: Asymmetry 2007, 18 (1), 142–148. DOI: 10.1016/j.tetasy.2006.12.022

17.Ordóñez, M.*; Hernández-Fernández, E.; Montiel-Pérez, M.; Bautista, R.; Bustos, P.; Rojas-Cabrera, H.; Fernández-Zertuche, M.; García-Barradas, O. A Convenient Method for the Preparation of Chiral Phosphonoacetamides and Their Horner–Wadsworth–Emmons Reaction. Tetrahedron: Asymmetry 2007, 18 (20), 2427–2436. DOI: 10.1016/j.tetasy.2007.09.033

2006

16.Hernández-Fernández, E.; Fernández-Zertuche, M.; García-Barradas, O.; Muñoz-Muñiz, O.; Ordóñez, M.* Practical and Efficient Synthesis of (E)-Α, β-Unsaturated Amides Bearing (S)-α-Methylbenzylamine from 2-Phosphonamides via Horner-Wadsworth-Emmons Reaction. Synlett 2006, 2006 (3), 440–444. Online

15. Poo, J. L.*; Góngora, J.; Sánchez-Ávila, F.; Aguilar-Castillo, S.; García-Ramos, G.; Fernández-Zertuche, M.; Rodríguez-Fragoso, L.; Uribe, M. Efficacy of Oral L-Ornithine-L-Aspartate in Cirrhotic Patients with Hyperammonemic Hepatic Encephalopathy. Results of a Randomized, Lactulose-Controlled Study. Ann Hepatol 2006, 5 (4), 281–288. Online

2005

14. De la Cruz-Cordero, R.; Hernándes-Núñez, E.; Fernández-Zertuche, M.; Muñoz-Hernández, M. A.; Ordóñez, M.* Preparation of Phosphostatine and Phosphoepistatine from L-Leucine via High Diastereoselective Reduction of 3-Amino-2-Ketophosphonates. ARKIVOC 2005, 6, 277–286. DOI: 10.3998/ark.5550190.0006.623

13.López-Cortina, S.; Basiulis, D. I.; Marsi, K. L.; Muñoz-Hernández, M. A.; Ordonez, M.; Fernández-Zertuche*, M. Synthesis of New 1, 3-Oxaphosphorinanium Salts. Stereochemistry of Hydroxide-Induced Displacement of Methoxide Ion. J. Org. Chem. 2005, 70 (19), 7473–7478. DOI: 10.1021/jo050901w

12.Meza-Aviña, M. E.; Ordoñez, M.; Fernández-Zertuche, M.*; Rodríguez-Fragoso, L.; Reyes-Esparza, J.; de los Ríos, A. A. M. Synthesis of Some Monocyclic Analogues of Mycophenolic Acid via the Johnson Ortho Ester Claisen Rearrangement. Bioorg. Med. Chem. 2005, 13 (23), 6521–6528. DOI: 10.1016/j.bmc.2005.07.013

2004

11.González-Morales, A.; Fernández-Zertuche, M.; Ordóñez, M.* Simultaneous Separation and Assignment of Absolute Configuration of γ-Amino-β-Hydroxyphosphonates by NMR Using (S)-Methoxyphenylacetic Acid (MPA). Rev. Soc. Quím. Méx 2004, 48, 239–245. Online

10. González-Morales, A.; Dı́az-Coutiño, D.; Fernández-Zertuche, M.; Garcı́a-Barradas, O.; Ordóñez, M.* Preparation of Dimethyl (R)-and (S)-2-(2-Aminophenyl)-2-Hydroxyethylphosphonate from Anthranilic Acid. Tetrahedron: Asymmetry 2003, 15 (3), 457–463. DOI: 10.1016/j.tetasy.2003.11.038

9. Ordóñez, M.*; De la Cruz-Cordero, R.; Fernández-Zertuche, M.; Muñoz-Hernández, M. A.; García-Barradas, O. Diastereoselective Reduction of Dimethyl γ-[(N-P-Toluenesulfonyl) Amino]-β-Ketophosphonates Derived from Amino Acids. Tetrahedron: Asymmetry 2004, 15 (19), 3035–3043. DOI: 10.1016/j.tetasy.2004.08.012

2003

8. Fernández-Zertuche, M.*; López-Cortina, S.; Meza-Aviña, M. E.; Ordóñez, M.; Ramírez-Solís, A. Generation of Alkoxyalkynylketenes from a Bicyclic Precursor. Cycloaddition Chemistry with Alkynes and Theoretical Studies Regarding the Formation of Five-versus Six-Membered Ring Products. ARKIVOC 2003, 11, 89–99. Online 

7. Flores-Morales, V.; Fernández-Zertuche, M.*; Ordóñez, M.* Highly Diastereoselective Addition of Et 2 AlCN to β-Keto Amides Derived from (S)-4-Isopropyl-2-Oxazolidinone. Tetrahedron: Asymmetry 2003, 14 (18), 2693–2698. DOI: 10.1016/j.tetasy.2003.07.004

6. Ordóñez, M.*; González-Morales, A.; Ruı́z, C.; De la Cruz-Cordero, R.; Fernández-Zertuche, M. Preparation of (R)-and (S)-γ-Amino-β-Hydroxypropylphosphonic Acid from Glycine. Tetrahedron: Asymmetry 2003, 14 (13), 1775–1779. DOI: 10.1016/S0957-4166(03)00371-9

2002

5. Ordonez, M.*; de la Gruz, R.; Fernandez‐Zertuche, M.; Munoz‐Hernandez, M. Diastereoselective Reduction of β‐Ketophosphonates Derived from Amino Acids. A New Entry to Enantiopure β‐Hydroxy‐γ‐aminophosphonate Derivatives. Thetrahedrom Asymmetry 2002, 13 (66), 559-562. DOI: 10.1016/S0957-4166(02)00159-3

4. Ordóñez, M.; De la Cruz-Cordero, R.; Fernández-Zertuche, M.; Muñoz-Hernández, M. A. Diastereoselective Reduction of γ-N, N-Dibenzylamino-β-Ketophosphonates γ-Substituted. Tetrahedron: Asymmetry 2002, 13, 559–562.

3. Fernández-Zertuche, M.*; Robledo-Pérez, R.; Meza-Aviña, M. E.; Ordoñez-Palacios, M. Allylic Strain Effects on the Stereochemistry of the Alkylation Reaction of Mycophenolic Acid Chiral Enolates. Tetrahedron Lett. 2002, 43 (20), 3777–3780. DOI: 10.1016/S0040-4039(02)00469-0

2. Ordóñez, M./*; de la Cruz, R.; Fernández-Zertuche, M.; Muñoz-Hernández, M.-Á. Diastereoselective Reduction of β-Ketophosphonates Derived from Amino Acids. A New Entry to Enantiopure β-Hydroxy-γ-Aminophosphonate Derivatives. Tetrahedron: Asymmetry 2002, 13 (6), 559–562. DOI: 10.1016/S0957-4166(02)00159-3

2000

1. Fernández-Zertuche, M.*; Hernández-Lamoneda, R.; Ramírez-Solís, A. Cyclic Allenes or Diradicals in the Cyclization Reactions of Dienynes Generated by Photolysis of Alkynylcyclohexadienones. J. Org. Chem. 2000, 65 (17), 5207–5211. DOI: 10.1021/jo000333e

• Síntesis de análogos de Baclofen. 
• Triazoles como análogos de GABA.
• 1,2,3-Triazoles-1,4 y 1,5-disubstituidos como análogos de GABA.
• Análogos de Baclofpen con estructuras de isoxazoles y 1,2,4-oxadiazoles. 
• Triazoles -4-Substituidos como análogos de GABA. 
• Síntesis de aminas heterocíclicas como precursores de derivados del antibiótico Anfotericina B.
•  Síntesis de triazoles 1,2,3-1,4-disubstituidos. 
• Análogos heterocíclicos de GABA.

1. Díaz  Peralta Lucero
2. Martínez Campos Zuleyma
3. Cruz Beltrán José Daniel
4. Nava Ocampo Ma. Guadalupe
5. Pérez Piña Víctor Manuel
6. Barragán Labastida Alma