SYNTHESIS AND CHARACTERIZATION OF NEW THEBAINE DERIVATIVES: 2-(6,14-ENDO-ETHENOTETRAHYDROTHEBAINE-7 alpha-YL)-5-(N-ARYLAMINO)-1,3,4-THIADIAZOLES


YAVUZ S. , YILDIRIR Y.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.187, sa.11, ss.1303-1311, 2012 (SCI İndekslerine Giren Dergi) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 187 Konu: 11
  • Basım Tarihi: 2012
  • Doi Numarası: 10.1080/10426507.2011.649499
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Sayfa Sayıları: ss.1303-1311

Özet

We have synthesized a series of novel 2-(6,14-endo-ethenotetrahydrothebaine-7 alpha-yl)-5-N-arylamino-1,3,4-thiadiazoles (5a-n) as potential narcotic analgesics, which are analogs of morphine. The synthesized compounds exhibit rigid morphine structures, including a 6,14-endo-entheno bridge and a 5-N-arylamino-1,3,4-thiadiazol-2-yl group at C-7 position that adopted S-configuration. The structures and stereochemistry of the compounds were completely assigned using one-and two-dimensional NMR experiments (H-1 NMR, APT, COSY, NOESY, HMQC, and HMBC), FTIR, and high-resolution mass spectral (HRMS) data.