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Your search keyword '"Sergio G. Duron"' showing total 6 results
Start Over Author "Sergio G. Duron" Topic chemistry.chemical_classification
6 results on '"Sergio G. Duron"'

1. Heteroaromatic-aminomethyl quinolones: Potent and selective iNOS inhibitors

Author

Nahid Yazdani, Peter J. Rix, Sergio G. Duron, Celine Bonnefous, Xiaohong Chen, Kent T. Symons, Yan Zhang, Hui Zhang, Li Wang, Stewart A. Noble, Nicholas D. Smith, Christian A. Hassig, Andrew K. Shiau, Natasha Rozenkrants, Tadimeti S. Rao, Andrew K. Lindstrom, and Marciano Sablad

Subjects
Models, Molecular, Pyrimidine, medicine.drug_class, Clinical Biochemistry, Nitric Oxide Synthase Type II, Pharmaceutical Science, Inflammation, Quinolones, Pharmacology, Crystallography, X-Ray, Ligands, Biochemistry, Nitric oxide, Structure-Activity Relationship, chemistry.chemical_compound, Drug Discovery, medicine, Humans, Enzyme Inhibitors, Overproduction, Molecular Biology, chemistry.chemical_classification, Dose-Response Relationship, Drug, Molecular Structure, biology, Organic Chemistry, Stereoisomerism, Quinolone, Nitric oxide synthase, Piperazine, Enzyme, chemistry, biology.protein, Molecular Medicine, medicine.symptom
Abstract

The overproduction of nitric oxide during the biological response to inflammation by the nitric oxide synthase (NOS) enzymes have been implicated in the pathology of many diseases. By removal of the amide core from uHTS-derived quinolone 4, a new series highly potent heteroaromatic-aminomethyl quinolone iNOS inhibitors 8 were identified. SAR studies led to identification of piperazine 22 and pyrimidine 32, both of which reduced plasma nitrates following oral dosing in a mouse lipopolysaccharide challenge assay.

Published
2012
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2. ChemInform Abstract: Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (-)-Crambidine

Author

Sergio G. Duron, David Y. Gin, Nicholas R. Perl, Sudeep Prajapati, Nathan D. Ide, and Hahdi H. Perfect

Subjects
chemistry.chemical_classification, Annulation, Nucleophile, Chemistry, Intramolecular force, Convergent synthesis, Alkyne, General Medicine, Hydroamination, Combinatorial chemistry, Crambidine
Abstract

A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

Published
2010
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3. Annulation of Thioimidates and Vinyl Carbodiimides to Prepare 2-Aminopyrimidines, Competent Nucleophiles for Intramolecular Alkyne Hydroamination. Synthesis of (−)-Crambidine

Author

Nicholas R. Perl, Sergio G. Duron, David Y. Gin, Sudeep Prajapati, Hahdi H. Perfect, and Nathan D. Ide

Subjects
chemistry.chemical_classification, Annulation, Convergent synthesis, Alkyne, Stereoisomerism, General Chemistry, Biochemistry, Catalysis, Article, Carbodiimides, Colloid and Surface Chemistry, Pyrimidines, Nucleophile, chemistry, Intramolecular force, Alkynes, Imidoesters, Organic chemistry, Spiro Compounds, Hydroamination, Amination, Guanidine
Abstract

A convergent synthesis of (−)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

Published
2010

4. Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines

Author

Michael Arnold, Sergio G. Duron, David Y. Gin, and Kenneth A. Day

Subjects
chemistry.chemical_classification, Annulation, Intramolecular reaction, Stereochemistry, Imine, Total synthesis, Stereoisomerism, General Chemistry, Biochemistry, Guanidines, Catalysis, Article, chemistry.chemical_compound, Carbodiimides, Colloid and Surface Chemistry, Polycyclic compound, Alkaloids, Pyrimidines, chemistry, Intramolecular force, Stereoselectivity, Imines, Amination
Abstract

A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.

Published
2006

5. Sulfide-mediated dehydrative glycosylation

Author

Hien M. Nguyen, David Y. Gin, Sergio G. Duron, and Yanning Chen

Subjects
chemistry.chemical_classification, Anomer, Glycosylation, Sulfide, Sulfonium, Oligosaccharides, Water, General Chemistry, Sulfides, Biochemistry, Combinatorial chemistry, Catalysis, carbohydrates (lipids), chemistry.chemical_compound, Colloid and Surface Chemistry, chemistry, Nucleophile, Reagent, Safrole, lipids (amino acids, peptides, and proteins), Glycosyl, Oxidation process, Glycoconjugates, Oxidation-Reduction
Abstract

The development of a new method for glycosylation with 1-hydroxy glycosyl donors employing dialkyl sulfonium reagents is described. The process employs the reagent combination of a dialkyl sulfide and triflic anhydride to effect anomeric bond constructions. This controlled dehydrative coupling of various C(1)-hemiacetal glycosyl donors and nucleophilic acceptors proceeds by way of a sulfide-to-sulfoxide oxidation process in which triflic anhydride serves as the oxidant.

Published
2001

6. Diastereoselective [4+2] Annulation of Vinyl Carbodiimides with N-Alkyl Imines. Asymmetric Synthetic Access to the Batzelladine Alkaloids

Author

David Y. Gin, Michael Arnold, and Sergio G. Duron

Subjects
Annulation, Vinyl Compounds, Alkylation, Stereochemistry, Guanidines, Biochemistry, Catalysis, Stereocenter, chemistry.chemical_compound, Alkaloids, Colloid and Surface Chemistry, Organic chemistry, Guanidine, Alkyl, chemistry.chemical_classification, Natural product, Chemistry, Enantioselective synthesis, Stereoisomerism, General Medicine, Batzelladine D, General Chemistry, Carbodiimides, Pyrimidines, Intramolecular force, Stereoselectivity, Organic synthesis, Imines
Abstract

A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich tricyclic core of the batzelladine alkaloids. Its application to the asymmetric synthesis of batzelladine D permitted the use of long-range, directed hydrogenation and stereoselective intramolecular iodoamination as additional key steps to establish the remaining stereocenters within the natural product with excellent stereocontrol.

Published
2005
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