Synthesis and structure-activity relationship studies of 3-biaryl-8-oxabicyclo[3.2.1]octane-2-carboxylic acid methyl esters

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Torun L., Madras B. K., Meltzer P. C.

BIOORGANIC & MEDICINAL CHEMISTRY, cilt.20, sa.8, ss.2762-2772, 2012 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 20 Sayı: 8
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1016/j.bmc.2012.01.053
  • Dergi Adı: BIOORGANIC & MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2762-2772
  • Yıldız Teknik Üniversitesi Adresli: Hayır

Özet

Stille cross coupling protocols were utilized for the synthesis of 3-(biaryl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylic acid methyl esters, which furnished products in high yields where in some cases Suzuki coupling under the conditions utilized provided complex reaction mixture. Samarium iodide reduction of the resulting coupling products produced both of the 2 beta-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers and the 2 alpha-carbomethoxy-3-biaryl-8-oxabicyclo[3.2.1]octane diastereomers. Among the series synthesized, the benzothiophene substituted compounds demonstrated significant binding profiles of inhibition of WIN 35,438 with 177-fold selectivity for DAT versus SERT. (C) 2012 Elsevier Ltd. All rights reserved.