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Papers by Michael Lilly

Research paper thumbnail of ChemInform Abstract: Stereochemical Control of the Intramolecular Diels-Alder Reaction by Remote Allylic Substituents on the Diene

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (+)-Crocacin D

Research paper thumbnail of Bicyclic Nucleosides and Nucleotides as Therapeutic Agents

Research paper thumbnail of Bycyclic nucleosides and nucleotides as therapeutic agents

Research paper thumbnail of Total Synthesis of (+)-Crocacin C

Research paper thumbnail of Viral polymerase inhibitors

Research paper thumbnail of Bicyclic nucleosides and nucleotides as therapeutic agents

Research paper thumbnail of ChemInform Abstract: Asymmetric Total Synthesis of the Myxobacteria Metabolites Crocacins A-D

Research paper thumbnail of Investigations into the stereochemical outcome of intramolecular Diels-Alder reactions : presented in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry at Massey University

... Progress in this area has set the scene for tandem TDA reactions to be attempted. Page 7.Adel... more ... Progress in this area has set the scene for tandem TDA reactions to be attempted. Page 7.Adele, Mum and Jim, Dad, Philip and Greg, Nanna Morris, Nanna Lilly and Grandy. Page 8. It gives me great pleasure to thank the following people for their help! ...

Research paper thumbnail of Viral polymerase inhibitors

Research paper thumbnail of ChemInform Abstract: New Insights into the endo-exo Stereoselectivity of the Intramolecular Diels-Alder Reaction of 1,3,8-Nonatrienes

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (-)-Reveromycin B

Research paper thumbnail of Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents

Bioorganic & medicinal chemistry letters, 2014

Previous investigations identified…

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (+)-Crocacin D

Research paper thumbnail of Asymmetric total synthesis of the myxobacteria metabolites crocacins A–D

Research paper thumbnail of Total Synthesis of Reveromycin B

Research paper thumbnail of On the Diels?Alder reactions of pentadienyl maleates and citraconates

Organic & Biomolecular Chemistry, 2005

Research paper thumbnail of Efficient Syntheses of Benzothiazepines as Antagonists for the Mitochondrial Sodium−Calcium Exchanger:  Potential Therapeutics for Type II Diabetes

The Journal of Organic Chemistry, 2003

Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular... more Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular, renal, neurologic, and retinal complications. While several drugs are currently prescribed to treat type II diabetes, their efficacy is limited by mechanism-related side effects (weight gain, hypoglycemia, gastrointestinal distress), inadequate efficacy for use as monotherapy, and the development of tolerance to the agents. Consequently, combination therapies are frequently employed to effectively regulate blood glucose levels. We have focused on the mitochondrial sodium-calcium exchanger (mNCE) as a novel target for diabetes drug discovery. We have proposed that inhibition of the mNCE can be used to regulate calcium flux across the mitochondrial membrane, thereby enhancing mitochondrial oxidative metabolism, which in turn enhances glucose-stimulated insulin secretion (GSIS) in the pancreatic beta-cell. In this paper, we report the facile synthesis of benzothiazepines and derivatives by S-alkylation using 2-aminobenzhydrols. The syntheses of other bicyclic analogues based on benzothiazepine, benzothiazecine, benzodiazecine, and benzodiazepine templates are also described. These compounds have been evaluated for their inhibition of mNCE activity, and the results from the structure-activity relationship (SAR) studies are discussed.

Research paper thumbnail of Total Synthesis of the Epidermal Growth Factor Inhibitor (−)-Reveromycin B

The Journal of Organic Chemistry, 2001

Research paper thumbnail of Allylic Stereocontrol of the Intramolecular Diels-Alder Reaction

Chemistry - A European Journal, 2005

The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonat... more The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonatrienes can be controlled by substituents about a stereogenic center attached to C1. The scope and limitations of this approach have been investigated, with variation in substrate structure about the allylic stereocenter and the dienophile. The stereochemical outcomes of these reactions are explained by reference to B3 LYP/6-31G(d) transition structures. New insights into the conformational preferences of allylic alcohol derivatives are reported, results which allow an explanation of the differing levels of pi-diastereofacial selectivity and cis/trans (i.e. endo/exo) selectivity from the reaction.

Research paper thumbnail of ChemInform Abstract: Stereochemical Control of the Intramolecular Diels-Alder Reaction by Remote Allylic Substituents on the Diene

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (+)-Crocacin D

Research paper thumbnail of Bicyclic Nucleosides and Nucleotides as Therapeutic Agents

Research paper thumbnail of Bycyclic nucleosides and nucleotides as therapeutic agents

Research paper thumbnail of Total Synthesis of (+)-Crocacin C

Research paper thumbnail of Viral polymerase inhibitors

Research paper thumbnail of Bicyclic nucleosides and nucleotides as therapeutic agents

Research paper thumbnail of ChemInform Abstract: Asymmetric Total Synthesis of the Myxobacteria Metabolites Crocacins A-D

Research paper thumbnail of Investigations into the stereochemical outcome of intramolecular Diels-Alder reactions : presented in partial fulfilment of the requirements for the degree of Doctor of Philosophy in Chemistry at Massey University

... Progress in this area has set the scene for tandem TDA reactions to be attempted. Page 7.Adel... more ... Progress in this area has set the scene for tandem TDA reactions to be attempted. Page 7.Adele, Mum and Jim, Dad, Philip and Greg, Nanna Morris, Nanna Lilly and Grandy. Page 8. It gives me great pleasure to thank the following people for their help! ...

Research paper thumbnail of Viral polymerase inhibitors

Research paper thumbnail of ChemInform Abstract: New Insights into the endo-exo Stereoselectivity of the Intramolecular Diels-Alder Reaction of 1,3,8-Nonatrienes

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (-)-Reveromycin B

Research paper thumbnail of Derivatives of imidazotriazine and pyrrolotriazine C-nucleosides as potential new anti-HCV agents

Bioorganic & medicinal chemistry letters, 2014

Previous investigations identified…

Research paper thumbnail of ChemInform Abstract: Total Synthesis of (+)-Crocacin D

Research paper thumbnail of Asymmetric total synthesis of the myxobacteria metabolites crocacins A–D

Research paper thumbnail of Total Synthesis of Reveromycin B

Research paper thumbnail of On the Diels?Alder reactions of pentadienyl maleates and citraconates

Organic & Biomolecular Chemistry, 2005

Research paper thumbnail of Efficient Syntheses of Benzothiazepines as Antagonists for the Mitochondrial Sodium−Calcium Exchanger:  Potential Therapeutics for Type II Diabetes

The Journal of Organic Chemistry, 2003

Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular... more Type II diabetes mellitus is a chronic metabolic disorder that can lead to serious cardiovascular, renal, neurologic, and retinal complications. While several drugs are currently prescribed to treat type II diabetes, their efficacy is limited by mechanism-related side effects (weight gain, hypoglycemia, gastrointestinal distress), inadequate efficacy for use as monotherapy, and the development of tolerance to the agents. Consequently, combination therapies are frequently employed to effectively regulate blood glucose levels. We have focused on the mitochondrial sodium-calcium exchanger (mNCE) as a novel target for diabetes drug discovery. We have proposed that inhibition of the mNCE can be used to regulate calcium flux across the mitochondrial membrane, thereby enhancing mitochondrial oxidative metabolism, which in turn enhances glucose-stimulated insulin secretion (GSIS) in the pancreatic beta-cell. In this paper, we report the facile synthesis of benzothiazepines and derivatives by S-alkylation using 2-aminobenzhydrols. The syntheses of other bicyclic analogues based on benzothiazepine, benzothiazecine, benzodiazecine, and benzodiazepine templates are also described. These compounds have been evaluated for their inhibition of mNCE activity, and the results from the structure-activity relationship (SAR) studies are discussed.

Research paper thumbnail of Total Synthesis of the Epidermal Growth Factor Inhibitor (−)-Reveromycin B

The Journal of Organic Chemistry, 2001

Research paper thumbnail of Allylic Stereocontrol of the Intramolecular Diels-Alder Reaction

Chemistry - A European Journal, 2005

The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonat... more The stereochemical outcome of the intramolecular Diels-Alder reaction of ester-linked 1,3,8-nonatrienes can be controlled by substituents about a stereogenic center attached to C1. The scope and limitations of this approach have been investigated, with variation in substrate structure about the allylic stereocenter and the dienophile. The stereochemical outcomes of these reactions are explained by reference to B3 LYP/6-31G(d) transition structures. New insights into the conformational preferences of allylic alcohol derivatives are reported, results which allow an explanation of the differing levels of pi-diastereofacial selectivity and cis/trans (i.e. endo/exo) selectivity from the reaction.

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