Medicinal Chemistry
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Ring Opening of Aziridines by Pendant Silanols Allows for Stereospecific Preparations of 1′-Amino-tetrahydrofurans
(American Chemical Society, 2023-05-30)We have developed a highly stereospecific cyclization of aziridine silanols into 1′-amino-tetrahydrofurans. Our protocol of stirring a substrate with 10 mol % Sc (OTf)3 and 1 equivalent of NaHCO3 in CH2Cl2 is mild and ... -
The Kappa Opioid Receptor Agonist 16-Bromo Salvinorin A Has Anti-Cocaine Effects without Significant Effects on Locomotion, Food Reward, Learning and Memory, or Anxiety and Depressive-like Behaviors
(MDPI, 2023-06-19)Kappa opioid receptor (KOR) agonists have preclinical antipsychostimulant effects; however, adverse side effects have limited their therapeutic development. In this preclinical study, conducted in Sprague Dawley rats, ... -
Covalent Tethers for Precise Amino Alcohol Syntheses: Ring Opening of Epoxides by Pendant Sulfamates and Sulfamides
(American Chemical Society, 2023-02-06)We describe the development of the first ring opening of epoxides using pendant sulfamates and sulfamides. These reactions are promoted by a base and proceed under mild conditions to afford oxathiazinanes and cyclic ... -
Sulfamate-Tethered Aza-Wacker Cyclization Strategy for the Syntheses of 2-Amino-2-deoxyhexoses: Preparation of Orthogonally Protected d-Galactosamines
(American Chemical Society, 2023-01-17)We present a new strategy for the assembly of protected d-galactosamine synthons. Our route uses a sulfamate-tethered aza-Wacker cyclization as a key step and commences from d-erythrono-1,4-lactone. This stands in contrast ... -
Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine
(American Chemical Society, 2022-08-11)We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine ... -
Highly Stereospecific Cyclizations of Homoallylic Silanols
(American Chemical Society, 2022-07-28)We demonstrate that di-tert-butylsilanols are competent nucleophiles for the intramolecular interception of palladium π-allyl species. In these reactions, allyl ethyl carbonates are the best precursors for the formation ... -
N-arylated oxathiazinane heterocycles are convenient synthons for 1,3-amino ethers and 1,3-amino thioethers
(Springer, 2020-05-17)This communication describes a variety of nucleophilic ring openings of N-arylated oxathiazinane heterocycles. We find that this reaction is compatible with phenoxides, naphthoxides, and thiolates and allows for the rapid ... -
Synthesis of Cycloheptatriene-Containing Azetidine Lactones
(American Chemical Society, 2022-05-23)We prepared a collection of complex cycloheptatriene-containing azetidine lactones by applying two key photochemical reactions: “aza-Yang” cyclization and Buchner carbene insertion into aromatic rings. While photolysis of ... -
Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates
(American Chemical Society, 2021-10-19)We present highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates. “Arming” the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity ... -
Oxidative Cyclization of Sulfamates onto Pendant Alkenes
(American Chemical Society, 2020-01-13)This communication discloses the first examples of aza-Wacker cyclizations of sulfamate esters. Within the realm of related cyclization reactions, this protocol is differential in that it forms six-membered rings in good ... -
Human cytochrome P450 17A1 structures with metabolites of prostate cancer drug abiraterone reveal substrate-binding plasticity and a second binding site
(Elsevier, 2023-03-09)Abiraterone acetate is a first-line therapy for castration-resistant prostate cancer. This prodrug is deacetylated in vivo to abiraterone, which is a potent and specific inhibitor of cytochrome P450 17A1 (CYP17A1). CYP17A1 ... -
Formulation Studies to Develop Low-cost, Orally-delivered Secretory IgA Monoclonal Antibodies for Passive Immunization Against Enterotoxigenic Escherichia coli (Dataset)
(Elsevier, 2023)Enterotoxigenic Escherichia coli (ETEC) is a common cause for diarrheal infections in children in low- and middle-income countries (LMICs). To date, no ETEC vaccine candidates have been approved. Passive immunization with ... -
Cellular Target Deconvolution of Small Molecules Using a Selection-Based Genetic Screening Platform
(American Chemical Society, 2022-09-22)Small-molecule drug target identification is an essential and often rate-limiting step in phenotypic drug discovery and remains a major challenge. Here, we report a novel platform for target identification of activators ... -
Combination Treatment of Withalongolide a Triacetate with Cisplatin Induces Apoptosis by Targeting Translational Initiation, Migration, and Epithelial to Mesenchymal Transition in Head and Neck Squamous Cell Carcinoma
(MDPI, 2022-12-19)Treatment regimens for head and neck squamous cell carcinoma (HNSCC) typically include cisplatin and radiotherapy and are limited by toxicities. We have identified naturally derived withalongolide A triacetate (WGA-TA) ... -
In-Depth Characterization of Endo-Lysosomal Aβ in Intact Neurons
(MDPI, 2022-08-20)Amyloid-beta (Aβ) peptides are produced within neurons. Some peptides are released into the brain parenchyma, while others are retained inside the neurons. However, the detection of intracellular Aβ remains a challenge ... -
Novel C-terminal heat shock protein 90 inhibitors target breast cancer stem cells and block migration, self-renewal, and epithelial–mesenchymal transition
(Wiley Open Access, 2020-04-07)In patients with triple-negative breast cancer (TNBC), evidence suggests that tumor-initiating cells (TIC) have stem cell-like properties, leading to invasion and metastasis. HSP90 plays a critical role in the conformational ... -
Flavin Metallaphotoredox Catalysis: Synergistic Synthesis in Water
(American Chemical Society, 2022-03-22)Combining a transition metal with a photocatalyst can drive modern synthetic chemistry. For transformations performed in water, this concept has been largely unexplored. We report the successful merger of a biocompatible ... -
Ring Opening of Epoxides by Pendant Silanols
(American Chemical Society, 2022-01-18)We present a new ring-opening reaction of epoxides by pendant silanols, catalyzed by either Ph3C+BF4– or BINOL-phosphoric acid. Silanol epoxides derived from trans-allylic alcohols, cis-allylic alcohols, trans-homoallylic ... -
Mutations in the Amyloid-β Protein Precursor Reduce Mitochondrial Function and Alter Gene Expression Independent of 42-Residue Amyloid-β Peptide
(IOS Press, 2021-09-28)Background:Dominant missense mutations in the amyloid-β protein precursor (AβPP) cause early-onset familial Alzheimer’s disease (FAD) and are associated with changes in the production or properties of the amyloid-β peptide ... -
Inhibition of SARS-CoV-2 by Targeting Conserved Viral RNA Structures and Sequences
(Frontiers Media, 2021-12-23)The ongoing COVID-19/Severe Acute Respiratory Syndrome CoV-2 (SARS-CoV-2) pandemic has become a significant threat to public health and has hugely impacted societies globally. Targeting conserved SARS-CoV-2 RNA structures ...
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