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Your search keyword '"J. Brad Shotwell"' showing total 3 results
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3 results on '"J. Brad Shotwell"'

1. Total Synthesis of Luminacin D

Author

J. Brad Shotwell, John S. Schneekloth, Brian Koh, John Hines, Evan S. Krygowski, John L. Wood, Craig M. Crews, Hui Won Choi, and Elliott W. D. Huntsman

Subjects
Tandem, Organic Chemistry, Convergent synthesis, chemistry.chemical_element, Total synthesis, Angiogenesis Inhibitors, Biochemistry, Combinatorial chemistry, Article, Samarium, chemistry.chemical_compound, Inhibitory Concentration 50, Structure-Activity Relationship, Aldol reaction, chemistry, Yield (chemistry), Benzaldehydes, Animals, Cattle, Spiro Compounds, Endothelium, Vascular, Physical and Theoretical Chemistry, Derivatization, Mode of action, Cell Division
Abstract

[reaction: see text] A highly convergent synthesis of the angiogenesis inhibitor luminacin D has been achieved in 13 linear steps (19 steps total, 5.3% overall yield) utilizing a samarium(II) iodide-mediated mixed tandem aldol/Evans-Tishchenko reaction to construct the carbohydrate precursor. The modular synthetic design will allow derivatization at key positions necessary for biochemical mode of action studies.

Published
2002

2. Stereoselective Syntheses of the C(1)−C(9) Fragment of Amphidinolide C.

Author

Robert H. Bates, J. Brad Shotwell, and William R. Roush

Subjects
*CEMENTUM annuli, *DENTAL annuli, *BIOSYNTHESIS, *BIOCHEMICAL engineering
Abstract

Stereoselective syntheses of the C(1)−C(9) fragments 18 and 28 of amphidinolide C have been developed. The first-generation sequence involves a diastereoselective chelate-controlled [3 + 2]-annulation reaction of 6and 7, while the second-generation synthesis involves an intramolecular hetero-Michael cyclization of 8. [ABSTRACT FROM AUTHOR]

Published
2008
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3. Optimization of a series of 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine inhibitors of IGF-1R: elimination of an acid-mediated decomposition pathway.

Author

Chamberlain SD, Redman AM, Patnaik S, Brickhouse K, Chew YC, Deanda F, Gerding R, Lei H, Moorthy G, Patrick M, Stevens KL, Wilson JW, and Brad Shotwell J

Subjects
Protein Kinase Inhibitors chemistry, Pyrimidines chemistry, Pyrroles chemistry, Acids chemistry, Protein Kinase Inhibitors pharmacology, Pyrimidines pharmacology, Pyrroles pharmacology, Receptor, IGF Type 1 antagonists & inhibitors
Abstract

Initial evaluation of a series 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidines revealed a C(1') carboxamide was preferred for sub-micromolar in vitro potency against IGF-1R. Subsequent solution stability studies with 1 revealed a susceptibility toward acid-induced intramolecular cyclization with the C(1') carboxamide. Herein, we describe several successful approaches toward generating both potent and acid-stable inhibitors of IGF-1R within the 4,6-bis-anilino-1H-pyrrolo[2,3-d]pyrimidine template.

Published
2009
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