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Microwave-assisted "libraries from libraries" approach toward the synthesis of allyl- and c-cyclopropylalkylamides

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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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Wipf, Ppwipf@pitt.eduPWIPF
Coleman, CM
Janjic, JM
Iyer, PS
Fodor, MD
Shafer, YA
Stephenson, CRJ
Kendall, C
Day, BW
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.pitt.edu/id/eprint/20407

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