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  • Nordqvist, AnneliUppsala universitet,Avdelningen för organisk farmaceutisk kemi (author)

Synthesis of Functionalized Cinnamaldehyde Derivatives by an Oxidative Heck Reaction and Their Use as Starting Materials for Preparation of Mycobacterium tuberculosis 1-Deoxy-D-xylulose-5-phosphate Reductoisomerase Inhibitors

  • Article/chapterEnglish2011

Publisher, publication year, extent ...

  • 2011-10-07
  • American Chemical Society (ACS),2011
  • electronicrdacarrier

Numbers

  • LIBRIS-ID:oai:DiVA.org:uu-158249
  • https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-158249URI
  • https://doi.org/10.1021/jo201715xDOI

Supplementary language notes

  • Language:English
  • Summary in:English

Part of subdatabase

Classification

  • Subject category:ref swepub-contenttype
  • Subject category:art swepub-publicationtype

Notes

  • Cinnamaldehyde derivatives were synthesized in good to excellent yields in one step by a mild and selective, base-free palladium(II)-catalyzed oxidative Heck reaction starting from acrolein and various arylboronic acids. Prepared α,β-unsaturated aldehydes were used for synthesis of novel α-aryl substituted fosmidomycin analogues, which were evaluated for their inhibition of Mycobacterium tuberculosis 1-deoxy-d-xylulose 5-phosphate reductoisomerase. IC(50) values between 0.8 and 27.3 μM were measured. The best compound showed activity comparable to that of the most potent previously reported α-aryl substituted fosmidomycin-class inhibitor.

Subject headings and genre

  • Pharmaceutical chemistry
  • Läkemedelskemi
  • Chemistry with specialization in Organic Chemistry
  • Kemi med inriktning mot organisk kemi

Added entries (persons, corporate bodies, meetings, titles ...)

  • Björkelid, ChristoferUppsala universitet,Struktur- och molekylärbiologi(Swepub:uu)chbjo425 (author)
  • Andaloussi, MounirUppsala universitet,Avdelningen för organisk farmaceutisk kemi (author)
  • Jansson, Anna M.Uppsala universitet,Struktur- och molekylärbiologi(Swepub:uu)anjan838 (author)
  • Mowbray, Sherry L.Uppsala universitet,Struktur- och molekylärbiologi(Swepub:uu)shmow020 (author)
  • Karlén, AndersUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)anderskl (author)
  • Larhed, MatsUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)matslarh (author)
  • Uppsala universitetAvdelningen för organisk farmaceutisk kemi (creator_code:org_t)

Related titles

  • In:Journal of Organic Chemistry: American Chemical Society (ACS)76:21, s. 8986-89980022-32631520-6904

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