Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3 ',4 '-tri-subsituted-1,2-dihydro-4H,4 ' H-spiro[isoquinoline-3,5 '-isoxazol]-4-ones

Ben Hadda T., Rahima B., Kerbal A., Bennani B., Al Houari G., Baba B. F., ...Daha Fazla

ARKIVOC, ss.1-13, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası:
  • Basım Tarihi: 2008
  • Doi Numarası: 10.3998/ark.5550190.0009.201
  • Dergi Adı: ARKIVOC
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1-13
  • Erciyes Üniversitesi Adresli: Evet

Özet

Synthesis of a series of fourteen novel 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones was accomplished in good yield by regio and stereoselective 1,3-dipolar cycloaddition of p-R-2-benzadoxime 4-8 with dipolarophiles (3Z)-3-[(4-substituted-phenyl)methylidene]-2-phenyl-2,3-dihydroisoquinolin-4(1H)-ones 1-3. The structure of the isolated products 9-23 was established through different spectroscopic techniques. X-Ray crystal structure analysis of one of the products confirms the structure and the selective region and stereochemistry of this cycloaddition. Their antitubercular activity is also evaluated.