Luis E Martinez | Trinity University, Texas (original) (raw)
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Papers by Luis E Martinez
Journal of the American Chemical Society Jacs, 2004
Bioorganic chemistry, 2014
The solid-phase synthesis of new amphiphilic compounds is reported. It is based on a newly design... more The solid-phase synthesis of new amphiphilic compounds is reported. It is based on a newly designed 1,4-naphthoquinone derivative that contains polar and nonpolar groups and self-assembles into micelles or vesicles in water depending on the concentration. They also display redox-active properties.
Biochemical and Biophysical Research Communications, 2005
Bioorganic & Medicinal Chemistry, 2004
Journal of the American Chemical Society, 1995
Page 1. J. Am. Chem. SOC. 1995,117, 5897-5898 5897 Highly Enantioselective Ring Opening of Epoxid... more Page 1. J. Am. Chem. SOC. 1995,117, 5897-5898 5897 Highly Enantioselective Ring Opening of Epoxides Catalyzed by (salen)Cr(III) Complexes Luis E. Martinez, James L. Leighton, Douglas H. Carsten, and Eric N. Jacobsen* ...
The Journal of Organic Chemistry, 1996
The development of synthetic routes to carbocyclic nucleoside analogs has attracted considerable ... more The development of synthetic routes to carbocyclic nucleoside analogs has attracted considerable attention, due partly to the interesting biological activity of these compounds and also to the persistent challenges associated with constructing substituted 5-membered carbocycles with defined relative and absolute stereochemistry. 3 Particularly noteworthy members of this class of compounds include the naturally-occurring carbocyclic adenosine analog (-)-aristeromycin (1), the biosynthesis 4 and biological activity 5 of which have been subject to recent intensive scrutiny; the related natural product (-)-3′-deoxyaristeromycin (2); 6 (-)-carbovir (3), a selective inhibitor of HIV reverse transcriptase in vitro; 7 and the structurally related (-)-1592U89 succinate (4), which has been reported to have a higher oral bioavailability than carbovir and is currently in clinical trials for the treatment of HIV infection ( ). 8 Our two groups recently uncovered effective catalysts for the highly selective synthesis and manipulation of 5-membered cyclic structures ). Complex 5, generated in situ by the combination of WOCl 4 and 2,6dibromophenol, is a useful and inexpensive catalyst for the ring-closing metathesis (RCM) of acyclic dienes to afford 5-and 6-membered cyclic compounds. 9 The (salen)Cr complex 6 has been identified as a catalyst for the asymmetric ring-opening (ARO) of meso and racemic epoxides by TMSN 3 , 10 with particularly high enantioselectivity displayed for the opening of epoxides fused to 5-membered rings. The sequential application of these two catalytic transformations, along with an intermediary epoxidation reaction, could constitute an efficient method for the conversion of simple dienes to cyclic 1,2amino alcohols wherein a new C-C bond has been constructed and two contiguous stereogenic centers have been established with high relative and absolute control ( ). In this paper, the power of this strategy is illustrated in the efficient synthesis of key intermediates leading to the carbocylic nucleoside analog structures outlined in .
ACS Chemical Biology, 2010
Tetrahedron Letters, 2005
A microwave-assisted solid-supported Dö tz benzannulation of chromium carbene complexes with vari... more A microwave-assisted solid-supported Dö tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1,4-naphthoquinone derivatives in good to moderate yields with high purities.
![Research paper thumbnail of Microwave-assisted iridium-catalyzed [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes](https://attachments.academia-assets.com/66058787/thumbnails/1.jpg)
](Tetrahedron Letters, 2007
The [Ir(COD)Cl] 2 /dppe system effectively catalyzes the solid-phase [2+2+2] cycloaddition of res... more The [Ir(COD)Cl] 2 /dppe system effectively catalyzes the solid-phase [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes under microwave conditions. The reaction results in high purity of isoindoline derivatives with moderate yields.
Energy & Fuels, 1997
Biaryl bonds are the strongest carbon-carbon single bonds in fossil fuels. This paper examines hy... more Biaryl bonds are the strongest carbon-carbon single bonds in fossil fuels. This paper examines hydrogenolysis and alkane cohydrogenolysis of biphenyl and dimethylbiphenyls, in detail. Biphenyl cleavage was found to be enhanced by copyrolysis and ...
Biochemical and Biophysical Research Communications, 2004
A simple fluorescence-based assay was developed for the rapid screening of potential cytotoxic co... more A simple fluorescence-based assay was developed for the rapid screening of potential cytotoxic compounds generated by combinatorial chemistry. The assay is based on detection of nuclear green fluorescent protein (GFP) staining of a human cervical cancer cell line (HeLa) carrying an integrated histone H2B-GFP fusion gene. Addition of a cytotoxic compound to the HeLa-GFP cells results in the eventual degradation of DNA and loss of the GFP nuclear fluorescence. Using this assay, we screened 11 distinct quinone derivatives and found that several of these compounds were cytotoxic. These compounds are structurally related to plumbagin an apoptosis-inducing naphthoquinone isolated from Black Walnut. In order to determine the mechanism by which cell death was induced, we performed additional experiments with the most cytotoxic quinones. These compounds were found to induce morphological changes (blebbing and nuclear condensation) consistent with induction of apoptosis. Additional tests revealed that the cytotoxic compounds induce both necrotic and apoptotic modes of death.
Bioorganic & Medicinal Chemistry, 2004
Mycobacterium tuberculosis is a serious worldwide health threat, killing almost 3 million people ... more Mycobacterium tuberculosis is a serious worldwide health threat, killing almost 3 million people per year. Other mycobacterial species, especially Mycobacterium avium, are emerging pathogens in the immunocompromised population, most notably AIDS patients. These nontuberculous mycobacteria (NTM) are ubiquitous in the environment, and naturally resistant to many disinfection procedures. Treatment options are limited, and no new antibiotics have been developed against mycobacteria since the 1970s. There is a desperate need for new biocides and antibiotics to prevent and treat mycobacterial infections. A small aromatic compound library has been screened for effectiveness in growth inhibition or killing of mycobacteria. Four species, representing the M. tuberculosis complex, the slow-growing NTM, and the rapid-growing NTM were used. Active compounds had minimal inhibitory concentrations as low as 12.5 lg/mL, with the active component being a quinone. The primarily bactericidal activity observed represents a unique mechanism of action. A fluorescent assay involving M. smegmatis expressing gfp was analyzed as a rapid assay for predicting inhibitory activity, but failed to predict activity well. Our compounds may have significant utility as soluble biocides against mycobacteria and other hardy nosocomial pathogens.
Biochemical and Biophysical Research Communications, 2005
A 96-well fluorescence-based assay has been developed for the rapid screening of potential cytoto... more A 96-well fluorescence-based assay has been developed for the rapid screening of potential cytotoxic and bacteriocidal compounds. The assay is based on detection of green fluorescent protein (GFP) in HeLa human carcinoma cells as well as gram negative (Escherichia coli) and gram positive bacteria (Mycobacterium avium). Addition of a toxic compound to the GFP marked cells resulted in the loss of the GFP fluorescence which was readily detected by fluorometry. Thirty-nine distinct naphthoquinone derivatives were screened and several of these compounds were found to be toxic to all cell types. Apart from differences in overall toxicity, two general types of toxic compounds were detected, those that exhibited toxicity to two or all three of the cell types and those that were primarily toxic to the HeLa cells. Our results demonstrate that the parallel screening of both eukaryotic and prokaryotic cells is not only feasible and reproducible but also cost effective.
Journal of the American Chemical Society Jacs, 2004
Bioorganic chemistry, 2014
The solid-phase synthesis of new amphiphilic compounds is reported. It is based on a newly design... more The solid-phase synthesis of new amphiphilic compounds is reported. It is based on a newly designed 1,4-naphthoquinone derivative that contains polar and nonpolar groups and self-assembles into micelles or vesicles in water depending on the concentration. They also display redox-active properties.
Biochemical and Biophysical Research Communications, 2005
Bioorganic & Medicinal Chemistry, 2004
Journal of the American Chemical Society, 1995
Page 1. J. Am. Chem. SOC. 1995,117, 5897-5898 5897 Highly Enantioselective Ring Opening of Epoxid... more Page 1. J. Am. Chem. SOC. 1995,117, 5897-5898 5897 Highly Enantioselective Ring Opening of Epoxides Catalyzed by (salen)Cr(III) Complexes Luis E. Martinez, James L. Leighton, Douglas H. Carsten, and Eric N. Jacobsen* ...
The Journal of Organic Chemistry, 1996
The development of synthetic routes to carbocyclic nucleoside analogs has attracted considerable ... more The development of synthetic routes to carbocyclic nucleoside analogs has attracted considerable attention, due partly to the interesting biological activity of these compounds and also to the persistent challenges associated with constructing substituted 5-membered carbocycles with defined relative and absolute stereochemistry. 3 Particularly noteworthy members of this class of compounds include the naturally-occurring carbocyclic adenosine analog (-)-aristeromycin (1), the biosynthesis 4 and biological activity 5 of which have been subject to recent intensive scrutiny; the related natural product (-)-3′-deoxyaristeromycin (2); 6 (-)-carbovir (3), a selective inhibitor of HIV reverse transcriptase in vitro; 7 and the structurally related (-)-1592U89 succinate (4), which has been reported to have a higher oral bioavailability than carbovir and is currently in clinical trials for the treatment of HIV infection ( ). 8 Our two groups recently uncovered effective catalysts for the highly selective synthesis and manipulation of 5-membered cyclic structures ). Complex 5, generated in situ by the combination of WOCl 4 and 2,6dibromophenol, is a useful and inexpensive catalyst for the ring-closing metathesis (RCM) of acyclic dienes to afford 5-and 6-membered cyclic compounds. 9 The (salen)Cr complex 6 has been identified as a catalyst for the asymmetric ring-opening (ARO) of meso and racemic epoxides by TMSN 3 , 10 with particularly high enantioselectivity displayed for the opening of epoxides fused to 5-membered rings. The sequential application of these two catalytic transformations, along with an intermediary epoxidation reaction, could constitute an efficient method for the conversion of simple dienes to cyclic 1,2amino alcohols wherein a new C-C bond has been constructed and two contiguous stereogenic centers have been established with high relative and absolute control ( ). In this paper, the power of this strategy is illustrated in the efficient synthesis of key intermediates leading to the carbocylic nucleoside analog structures outlined in .
ACS Chemical Biology, 2010
Tetrahedron Letters, 2005
A microwave-assisted solid-supported Dö tz benzannulation of chromium carbene complexes with vari... more A microwave-assisted solid-supported Dö tz benzannulation of chromium carbene complexes with various alkynes has been developed. The oxidative cleavage of the resulting resin-bound 1,4-naphthols affords 2,3-disubstituted-1,4-naphthoquinone derivatives in good to moderate yields with high purities.
Tetrahedron Letters, 2007
The [Ir(COD)Cl] 2 /dppe system effectively catalyzes the solid-phase [2+2+2] cycloaddition of res... more The [Ir(COD)Cl] 2 /dppe system effectively catalyzes the solid-phase [2+2+2] cycloaddition of resin-bound dipropargylamine with alkynes under microwave conditions. The reaction results in high purity of isoindoline derivatives with moderate yields.
Energy & Fuels, 1997
Biaryl bonds are the strongest carbon-carbon single bonds in fossil fuels. This paper examines hy... more Biaryl bonds are the strongest carbon-carbon single bonds in fossil fuels. This paper examines hydrogenolysis and alkane cohydrogenolysis of biphenyl and dimethylbiphenyls, in detail. Biphenyl cleavage was found to be enhanced by copyrolysis and ...
Biochemical and Biophysical Research Communications, 2004
A simple fluorescence-based assay was developed for the rapid screening of potential cytotoxic co... more A simple fluorescence-based assay was developed for the rapid screening of potential cytotoxic compounds generated by combinatorial chemistry. The assay is based on detection of nuclear green fluorescent protein (GFP) staining of a human cervical cancer cell line (HeLa) carrying an integrated histone H2B-GFP fusion gene. Addition of a cytotoxic compound to the HeLa-GFP cells results in the eventual degradation of DNA and loss of the GFP nuclear fluorescence. Using this assay, we screened 11 distinct quinone derivatives and found that several of these compounds were cytotoxic. These compounds are structurally related to plumbagin an apoptosis-inducing naphthoquinone isolated from Black Walnut. In order to determine the mechanism by which cell death was induced, we performed additional experiments with the most cytotoxic quinones. These compounds were found to induce morphological changes (blebbing and nuclear condensation) consistent with induction of apoptosis. Additional tests revealed that the cytotoxic compounds induce both necrotic and apoptotic modes of death.
Bioorganic & Medicinal Chemistry, 2004
Mycobacterium tuberculosis is a serious worldwide health threat, killing almost 3 million people ... more Mycobacterium tuberculosis is a serious worldwide health threat, killing almost 3 million people per year. Other mycobacterial species, especially Mycobacterium avium, are emerging pathogens in the immunocompromised population, most notably AIDS patients. These nontuberculous mycobacteria (NTM) are ubiquitous in the environment, and naturally resistant to many disinfection procedures. Treatment options are limited, and no new antibiotics have been developed against mycobacteria since the 1970s. There is a desperate need for new biocides and antibiotics to prevent and treat mycobacterial infections. A small aromatic compound library has been screened for effectiveness in growth inhibition or killing of mycobacteria. Four species, representing the M. tuberculosis complex, the slow-growing NTM, and the rapid-growing NTM were used. Active compounds had minimal inhibitory concentrations as low as 12.5 lg/mL, with the active component being a quinone. The primarily bactericidal activity observed represents a unique mechanism of action. A fluorescent assay involving M. smegmatis expressing gfp was analyzed as a rapid assay for predicting inhibitory activity, but failed to predict activity well. Our compounds may have significant utility as soluble biocides against mycobacteria and other hardy nosocomial pathogens.
Biochemical and Biophysical Research Communications, 2005
A 96-well fluorescence-based assay has been developed for the rapid screening of potential cytoto... more A 96-well fluorescence-based assay has been developed for the rapid screening of potential cytotoxic and bacteriocidal compounds. The assay is based on detection of green fluorescent protein (GFP) in HeLa human carcinoma cells as well as gram negative (Escherichia coli) and gram positive bacteria (Mycobacterium avium). Addition of a toxic compound to the GFP marked cells resulted in the loss of the GFP fluorescence which was readily detected by fluorometry. Thirty-nine distinct naphthoquinone derivatives were screened and several of these compounds were found to be toxic to all cell types. Apart from differences in overall toxicity, two general types of toxic compounds were detected, those that exhibited toxicity to two or all three of the cell types and those that were primarily toxic to the HeLa cells. Our results demonstrate that the parallel screening of both eukaryotic and prokaryotic cells is not only feasible and reproducible but also cost effective.