Margarita Ortiz-Marciales, Ph. D.

Catedrática

UPRH-Chemistry

margarita.ortiz1@upr.edu; ortiz@quimica.uprh.edu

787-850-9469; 787-852-3222; Lab. 787-850-0000 ext. 9182

Oficina: CNO  243

 

 

 

Education

Pot-Doc 1980-81, Organometallic Chemistry, UPR-Río Piedras 

Ph. D. 1979 – Organic Chemistry, University of Alabama, Tuscaloosa

 M. Sc. 1973 – Physical Organic Chemistry, University of Alabama, Huntsville

BS 1968 – Chemistry, Universidad Nacional de Colombia, Bogota

 

 

 

Teaching Courses

Organic Chemistry I II( QUIM 3031, QUIM 3032, QUIM 3033, QUIM 3034)

 

 

 

Research

The main goal of our research is to develop novel asymmetric synthetic methodologies using organic boron compounds as chirality transfer agents, and apply this chemistry for the preparation of important chiral drugs. Our present interest lays in the synthesis of potential drugs that can affect different cholinergic pathways, and that could be valuable for the treatment of neuron-degenerative diseases, such as Alzheimer and Parkinson. The PI has been able to establish and develop a competitive biomedical research area, and she has being able to contribute significantly to scientific advancements in Synthetic Organic Chemistry and Medicinal Chemistry, as shown by the publication record in which the PI is the corresponding author. Our research group consists of a postdoctoral investigator, a research technician, graduate and undergraduate students and a collaborator, Dr. Carmelo Garcia at our Institution, and by in collaboration with NIH-INBRE Program, Dr. José Lasalde, from Neurobiology Department at the University of Puerto Rico, Río Piedras. Presently, the PI has a well established research laboratory at UPR-Humacao with excellent instrumentation, such as a 400 MHz for multinuclear analysis, a GC/MS, FT-IR with ATR, a modern Polarimeter and HPLC and GC’s with chiral columns.

 

 

 

 

 

 

 

 

 


Figure 1. Novel Spiroaminoborate Esters

 

 

 

 

 

 

 

 

 

 

Figure 2.  X-Ray Structure of Spiroaminoborate 6

 

 

 

Figure 3. X-Ray Structure of CBS Oxazaborolidine-Borane Complex Dimer

 

 

 

 

 

 

 

 

 

 

 


Figure 4. X-Ray Structure of DimethoxyAmino Borate

 

 

 

Proposals

NIH/NIGMS/SCORE  SO6-GM08216 (P.D. A. E. Alegría); Role: PI ; 4/1/07 - 3/31/11                                                           

New Methodologies for the Synthesis of Biological Active Amino Derivatives         

The major goal of this project is to develop new chemistry using organoborane reagents for the preparation of alcohols and primary amines used as intermediaries or reagents for the synthesis of important biological products.

NIH/INBRE NC P20 RR-016470 (P.D. F. González) Role: PI; 7/1/09 - 6/31/14; $125,000 ańo   

New Methodologies for the Synthesis of Amino Derivatives as Nicotinic Receptor Agonists.           

The main goal of this project is to develop novel organic synthetic methodology for the preparation of potential nicotinic receptor agonist that will be valuable for the treatment of neuron-degenerative diseases, such Alzheimer and Parkinson.

 

 

 

Publications

 

 

 

 

 

 

12.  M. Ortiz-Marciales, M. De Jesús, D. Figueroa, J. Hernández, L. Vázquez,  R. Vega, J. A. López, “A General Uncatalyzed  Method for the Synthesis of O-Silylated Oximes”  Synthetic Comm. 2003, 2, 309. 13. M. Ortiz-Marciales, Eduvigis González, Ruth Fiqueroa,* Melvin DeJesús,* Johanna Martínez,* Sandraliz Espinosa* and Wildeliz Correa, “Efficient Synthesis of B-alkylated Oxazaborolidines Derived from Ephedrine and Norephedrine”, Organic Lett. 2003, 5, 3447-3449. PMCI: PMC2811074.

14.  M. Ortiz-Marciales, M. De Jesús, E. González, R. G. Raptis and P. Baran, “1,3,2-Oxazaborolidine Dimer  Derived from (S)-α,α-Diphenyl Prolinol”, Acta Cryst. C 2004, 60, 173-175.PMCID: PMC2814345

15.   Nicholas J. Pinto, Pedro L. Carrión,* Angel M. Ayala,* M. Ortiz-Marciales, “Temperature Dependence of the Resistance of Self Assembled Polyaniline Nanotubes doped with 2-Acrylamido-2-methyl-1-propanesulfonic acid”, Synthetic Metals 2005, 148, 271–274.

16.  Margarita Ortiz-Marciales, L. D. Rivera, * M. De Jesús, S. Espinosa, J. A. Benjamin,* O. E. Casanova,* I. G. Figueroa* and W. Correa.* Facile Rearrangement of O-Silylated Oximes on Reduction with Borane / Boron Trifluoride”, J. Org. Chem 2005, 70, 10132-10134.

17.  V. Stepanenko, M. Ortiz-Marciales, W. Correa, M. DeJesús, S.           Espinosa and L. Ortiz,* “Highly Enantioselective Carbonyl Reduction with Borane Catalyzed by Chiral Spiroborate esters Derived from Chiral 1,2-Aminoalcohols”, Tetrahedron Asymmetry            2006,17,112-115.

18.  V. Stepanenko, M. Ortiz-Marciales, C. E. Barnes and C. Garcia,Studies on the Synthesis of Borazines from Borane and 1,2 –Amino Alcohols”, Tetrahedron Letters 2006, 47, 7603-7606.

19.  X. Huang, M. Ortiz-Marciales, V. Stepanenko, F. G. Merced,* A. M. Ayala* and M. De Jesús, Spiroborate Esters Derived from Non-racemic 1,2-Aminoalcohols as Efficient Catalysts  in the Enantioselective Synthesis of Primary Amines via Borane Reduction of Oxime Ethers” Organic Lett. 2007, 9, 1793-1795. PMCID:PMC2571073.

20.  V. Stepanenko, M. de Jesús, W. Correa, I. Guzmán,* C. Vázquez,* W. de la Cruz*, M. Ortiz-Marciales, C. E. Barnes,Enantioselective Reduction of Prochiral Ketones using Spiroborate Esters as                           Catalysts”, Tetrahedron Lett. 2007, 48, 5799-5802. PMCID: PMC2701200.

21.  V. Stepanenko, M. Ortiz-Marciales, M. De Jesús, W. Correa, C. Vázquez,* L. Ortiz,* Irisbel Guzmán* and W. de la Cruz*,Highly Enantioselective Reduction of Acetylpyridines and other Heteroaromatic Ketones with Borane and Spiroborate Esters”, Tetrahedron Asymmetry 2007, 18, 2738-2745.

22.  K. Huang, M. Ortiz-Marciales, F. G. Merced,* H. J. Meléndez,* W. Correa, M. De Jesús, “Highly Enantioselective Borane Reduction of Heteroaryl and Heterocyclic Ketoxime Ethers Catalyzed by Novel Spiroborate Ester derived from Diphenyl Valinol: Application to the Synthesis of Nicotine Analogues”, J. Org. Chem. 2008,73,4017-4026.  PMCID: PMC2701197.

23.   K. Huang, M. Ortiz-Marciales, V. Stepanenko, M. De Jesús and W. Correa, “A Practical and Efficient Route for the Highly Enantioselective Synthesis of Mexiletine Analogues                         and Novel β-Thiophenoxy and Pyridyl Ethers”, J. Org. Chem. 2008, 73, 6928-6931. PMCI: PMC2668572.

24V. Stepanenko, M. Ortiz-Marciales, C. L. Barnes and C.Garcia, “Novel Dimethoxy-(aminoalkoxy)borate derived from (S)-Diphenylprolinol as highly Efficient Catalyst for             the Enantioselective Boron-mediated reduction of prochiral ketones”, Tetrahedron Letters 2009, 50, 995-998. PMCID: PMC2654321. 

25.  K. Huang, M. Ortiz-Marciales, W. Correa, X. Y. López* and E. Pomales*, Spiroborate Ester-Mediated Asymmetric Synthesis of b-Hydroxy Ethers and its Conversion to                   Highly Enantiopure b-Amino Ethers, J. Org. Chem. 2009, 74, 4195.  PMCI: PMC2811585.

26.   K. Huang, M. Ortiz-Marciales*and V. Stepanenko, A New and Efficient Approach to the Synthesis of Nicotine and Anabasine Analogues, J. Heterocyclic Chem.2009, 46, 1252. PMCID: PMC2811074.

 27.   V. Stepanenko, M. De Jesús, W. Correa, L. Bermúdez, * C. Vázquez, * I. Guzmán* and M. Ortiz-Marciales, Chiral Spiroaminoborate Ester as a Highly Enantioselective and Efficient  Catalyst for the Borane Reduction of Furyl, Thiophene, Chroman and Thiochroman  containing Ketones, Tetrahedron Asymmetry 2009, 20, 2659. PMCID: PMC2808030.  

28.  V. Stepanenko, K. Huang and M. Ortiz-Marciales, Synthesis of Spiroborate Esters from 1,2-Amino Alcohols, Ethylene Glycol and Triisopropylborate: Preparation of  (S)- 1-(1,3,2-Dioxaborola-2-yloxy)-3-Methyl-1,1-Diphenylbutan-2-Amine”, Organic Synthesis 2010, 87, 26.

29.   K. Huang, M. Ortiz-Marciales, Catalytic Enantioselective Borane Reduction of Benzyloximes: Preparation of (S)-1-Pyridin-3-yl-ethylamine Hydrochloride, Organic Synthesis 2010, 87, 36.

30.  K. Huang, H. Wang, V. Stepanenko,  M. De Jesús, C. Torruellas,       W. Correa and M. Ortiz-Marciales, Highly Efficient Synthesis of Chiral Epoxides via Borane Reduction of 2-Haloketones Catalyzed By Spiroborate Ester: Application to the Synthesis of Optically Pure 1,2-Hydroxy Ethers and 1,2-Azido Alcohols,  J. Org. Chem., on line in the web February 4  2011.  

* Undergraduate students, **Graduate student

 

 

Patents

 

1.  Margarita Ortiz-Marciales, M. DeJesús, E. González, S. Espinosa and W. Correa, A New and Convenient Synthesis of B-alkyl Oxazaborolidines Derived from Ephedrine and Norephedrine, US Patent Office, # 10/775,011, Feb. 9, 2004 .

2. Margarita Ortiz-Marciales, Viatcheslav Stepanenko, Melvin DeJesús and Wildeliz Correa, “Highly enantioselective carbonyl reduction with borane catalyzed by chiral spiroborate esters derived from chiral 1,2-aminoalcohols”, submitted as a pending US Patent Application # 11/512,599, in Aug. 30, 2006. iEdison # 0578705-02-0001. 

3.  Margarita Ortiz-Marciales, Xiaogen Huang, Viatcheslav Stepanenko, Melvin DeJesús, Wildeliz Correa, “Catalytic Asymmetric Synthesis of Primary Amines via Borane Reduction of Oxime Ethers using Spiroborate Esters”, submitted as pending # 60/841,147, in Aug. 30, 2006. iEdison # 0578705-06-0002, June 23, 2006, and filed as an International application on Aug 17, 2007: PTC application No PCT/US07/76195.

4.  Margarita Ortiz-Marciales, Kun Huang, Viatcheslav Stepanenko Melvin De Jesús and Wildeliz Correa, A Practical and Efficient Route for the Highly Enantioselective Synthesis of Mexiletine Analogues and Novel β-Thiophenoxy and Pyridyl Ethers” submitted as US Patent Application, April 15, 2009.

5.  José Lasalde, Neurobiology Department, UPR Río Piedras, Margarita Ortiz-Marciales, Chemistry Department, UPR Humacao, Daisy Espinosa, Chemistry Department, UPR Río Piedras, Allosteric Modulator of Nicotinic Receptor as a Therapeutic Drug for Alzheimer’s Disease (AD) submitted as a provisional US Patent Application, July 2010.