title: From bead to flask: Synthesis of a complex β-amido-amide for probe-development studies.
abstract: A concise synthesis of benzimidazole-substituted β-amido-amide LLW62 is presented. The original synthesis of compounds related to LLW62 was developed on Rink resin as part of a "one-bead, one-compound" combinatorial approach for on-bead screening purposes. The current synthesis is carried out in solution and is amenable to scale-up for follow-up studies on LLW62 and investigations of related structures. The key step involves the use of a β-amino acid-forming three-component reaction (3CR), the scope of which defines its role in the synthetic strategy.
authors: Department of Chemistry, University of California, Davis, CA 95616, USA ; Comparative Pathology Graduate Group, University of California, Davis, CA 95616, USA.
authors: Kevin S
authors: KS
authors: Martin
authors: Cristian
authors: C
authors: Soldi
authors: Kellan N
authors: KN
authors: Candee
authors: Hiromi I
authors: HI
authors: Wettersten
authors: Robert H
authors: RH
authors: Weiss
authors: Jared T
authors: JT
authors: Shaw
keywords: benzimidazole; multicomponent reaction; β-amino acid
references: Bioorg Med Chem. 2002 Aug;10(8):2589-96
references: 12057648
references: Cancer Cell. 2003 Dec;4(6):425-9
references: 14706334
references: J Urol. 2008 Jul;180(1):352-60
references: 18499163
references: Bioorg Med Chem Lett. 2007 Jan 1;17(1):63-7
references: 17049849
references: J Comb Chem. 2007 Jan-Feb;9(1):143-57
references: 17206843
references: J Med Chem. 2006 Dec 14;49(25):7413-26
references: 17149871
references: Nature. 1991 Nov 7;354(6348):82-4
references: 1944576
references: Mol Cancer Ther. 2010 Oct;9(10):2714-23
references: 20858725
references: J Comb Chem. 2010 Nov 8;12(6):765-806
references: 20923157
references: Bioorg Med Chem. 2011 May 1;19(9):2903-10
references: 21481591
references: Anal Biochem. 2008 Mar 1;374(1):112-20
references: 18023409
references: Chem Commun (Camb). 2011 Sep 21;47(35):9757-63
references: 21701754
references: Cancer Biol Ther. 2008 Dec;7(12):2015-22
references: 18981726
references: Mol Cancer Ther. 2005 May;4(5):806-13
references: 15897245
references: Chemistry. 2009 Oct 5;15(39):10144-57
references: 19697384
references: Methods Enzymol. 2003;369:298-322
references: 14722961
references: J Urol. 2007 Jan;177(1):63-8; discussion 68-9
references: 17162001
references: Urol Oncol. 2012 Sep;30(5):635-45
references: 20888272