Literature DB >> 17855098

Direct diazo-transfer reaction on beta-lactam: synthesis and preliminary biological activities of 6-triazolylpenicillanic acids.

Po C Chen1, Rebekah E Wharton, Pratiq A Patel, Adegboyega K Oyelere.   

Abstract

In this study we report the first example of a direct diazo-transfer reaction on readily available 6-aminopenicillanates to give 6-azidopenicillanates in high yield. Subsequent Cu(I)-catalyzed Huisgen cycloaddition between these 6-azidopenicillanates and assorted terminal alkynes facilely furnished 6-triazolylpenicillanic acids. Preliminary biological screening indicates that these triazolylpenicillanic acids possess low to moderate antibacterial activities.

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Year:  2007        PMID： 17855098      PMCID： PMC2755539          DOI： 10.1016/j.bmc.2007.08.035

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  43 in total

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4.  Structure-activity relationship of 6-methylidene penems bearing 6,5 bicyclic heterocycles as broad-spectrum beta-lactamase inhibitors: evidence for 1,4-thiazepine intermediates with C7 R stereochemistry by computational methods.

Authors:  Aranapakam M Venkatesan; Atul Agarwal; Takao Abe; Hideki Ushirogochi; Itsuka Yamamura; Mihira Ado; Takasaki Tsuyoshi; Osvaldo Dos Santos; Yansong Gu; Fuk-Wah Sum; Zhong Li; Gerry Francisco; Yang-I Lin; Peter J Petersen; Youjun Yang; Toshio Kumagai; William J Weiss; David M Shlaes; James R Knox; Tarek S Mansour
Journal:  J Med Chem       Date:  2006-07-27       Impact factor: 7.446

5.  Ab initio QM/MM study of class A beta-lactamase acylation: dual participation of Glu166 and Lys73 in a concerted base promotion of Ser70.

Authors:  Samy O Meroueh; Jed F Fisher; H Bernhard Schlegel; Shahriar Mobashery
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

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Journal:  J Biol Chem       Date:  1999-09-03       Impact factor: 5.157

7.  Beta-lactam screening by specific residues of the OmpF eyelet.

Authors:  Stéphanie Vidal; Jérôme Bredin; Jean-Marie Pagès; Jacques Barbe
Journal:  J Med Chem       Date:  2005-03-10       Impact factor: 7.446

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Review 9.  The art of fusion: from penams and cephems to penems.

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Journal:  Chemotherapy       Date:  2003-06       Impact factor: 2.544

10.  1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.

Authors:  Victoria D Bock; Dave Speijer; Henk Hiemstra; Jan H van Maarseveen
Journal:  Org Biomol Chem       Date:  2007-02-06       Impact factor: 3.876
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  4 in total

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Authors:  Arren Z Washington; Subhasish Tapadar; Alex George; Adegboyega K Oyelere
Journal:  Bioorg Med Chem       Date:  2015-05-06       Impact factor: 3.641

2.  One-pot phosphine-catalyzed syntheses of quinolines.

Authors:  San Khong; Ohyun Kwon
Journal:  J Org Chem       Date:  2012-09-06       Impact factor: 4.354

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Journal:  J Med Chem       Date:  2013-12-12       Impact factor: 7.446

4.  Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and β-amino alcohols.

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Journal:  Molecules       Date:  2011-05-05       Impact factor: 4.411
  4 in total

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