@article{67763edcf0d44f5da0aa8e19372bc2b0,
title = "Ortho group activation of a bromopyrrole ester in Suzuki-Miyaura cross-coupling reactions: Application to the synthesis of new microtubule depolymerizing agents with potent cytotoxic activities",
abstract = "New microtubule depolymerizing agents with potent cytotoxic activities have been prepared with a 5-cyano or 5-oximino group attached to a pyrrole core. The utilization of ortho activation of a bromopyrrole ester to facilitate successful Suzuki-Miyaura cross-coupling reactions was a key aspect of the synthetic methodology. This strategy allows for control of regiochemistry with the attachment of four completely different groups at the 2, 3, 4 and 5 positions of the pyrrole scaffold. Biological evaluations and molecular modeling studies are reported for these examples.",
keywords = "Cytotoxic activity, Marine natural products, Microtubule inhibitors, Pyrrole, Suzuki-Miyaura cross-coupling",
author = "Gupton, {John T.} and Scott Yeudall and Nakul Telang and Megan Hoerrner and Ellis Huff and Evan Crawford and Katie Lounsbury and Michael Kimmel and William Curry and Andrew Harrison and Wen Juekun and Alex Shimozono and Joe Ortolani and Kristin Lescalleet and Jon Patteson and Veronica Moore-Stoll and Rohena, {Cristina C.} and Mooberry, {Susan L.} and Obaidullah, {Ahmad J.} and Kellogg, {Glen E.} and Sikorski, {James A.}",
note = "Funding Information: We gratefully thank the National Institutes of Health ? United States grant R15-CA67236 (JTG) and the Greehey Distinguished Chair in Targeted Molecular Therapeutics (SLM) for support of this research. Thanks also to the Floyd D. and Elisabeth S. Gottwald Endowment and to the University of Richmond Faculty Research Grant program for support to JTG. We are exceedingly grateful to Mr. Dave Patteson formerly of Biotage Inc. for the generous donation of an SP-1 flash chromatography system, which was used in the majority of sample purifications. We are also very appreciative of Advion Inc. for the generous donation of a CMS electrospray mass spectrometer. Previous grants from the MRI program of the National Science Foundation ? United States for the purchase of a 500?MHz NMR spectrometer (CHE-0116492) and a high resolution electrospray mass spectrometer (CHE-0320669) are also gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",
year = "2017",
doi = "10.1016/j.bmc.2017.04.012",
language = "English (US)",
volume = "25",
pages = "3206--3214",
journal = "Bioorganic and Medicinal Chemistry",
issn = "0968-0896",
publisher = "Elsevier Limited",
number = "12",
}