Wipf, P and Coleman, CM and Janjic, JM and Iyer, PS and Fodor, MD and Shafer, YA and Stephenson, CRJ and Kendall, C and Day, BW
(2005)
Microwave-assisted "libraries from libraries" approach toward the synthesis of allyl- and c-cyclopropylalkylamides.
Journal of Combinatorial Chemistry, 7 (2).
322 - 330.
ISSN 1520-4766
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Abstract
Cascade reactions of internal and terminal alkynes, zirconocene hydrochloride, dimethylzinc, and phosphinoyl imines (prepared in one step from aldehydes and diphenylphosphinoyl amide) lead to allylic phosphinoyl amides after aqueous workup. Microwave acceleration allows the completion of this one-pot reaction sequence in 10 min. These allylic amides can be converted into a variety of derivatives, including carbamates and sulfonamides, or reacted prior to workup with diiodomethane to give novel C-cyclopropylalkylamides. A solution-phase "libraries from libraries" approach was used to generate an intermediate 20-member library which was subsequently expanded to a 100-member library by a series of N-functionalizations. The biological activity was evaluated in an assay for competitive binding to the estrogen receptor (ERa), revealing three potent lead compounds of a new structural type. © 2005 American Chemical Society.
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Item Type: |
Article
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Status: |
Published |
Creators/Authors: |
Creators | Email | Pitt Username | ORCID ![](/images/orcid_id_24x24.png) |
---|
Wipf, P | pwipf@pitt.edu | PWIPF | | Coleman, CM | | | | Janjic, JM | | | | Iyer, PS | | | | Fodor, MD | | | | Shafer, YA | | | | Stephenson, CRJ | | | | Kendall, C | | | | Day, BW | | | |
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Date: |
1 March 2005 |
Date Type: |
Publication |
Journal or Publication Title: |
Journal of Combinatorial Chemistry |
Volume: |
7 |
Number: |
2 |
Page Range: |
322 - 330 |
DOI or Unique Handle: |
10.1021/cc049842a |
Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
Refereed: |
Yes |
ISSN: |
1520-4766 |
MeSH Headings: |
Allyl Compounds--chemical synthesis; Allyl Compounds--chemistry; Allyl Compounds--pharmacology; Amides--chemical synthesis; Amides--chemistry; Amides--pharmacology; Binding, Competitive; Combinatorial Chemistry Techniques--methods; Estrogen Receptor alpha--chemistry; Microwaves; Molecular Structure; Structure-Activity Relationship |
PubMed ID: |
15762763 |
Date Deposited: |
30 Jan 2014 17:57 |
Last Modified: |
02 Feb 2019 15:57 |
URI: |
http://d-scholarship-dev.library.pitt.edu/id/eprint/20407 |
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