Bioisosteric hybrids of two anti-inflammatory agents, rutaecarpine and piroxicam

Máté Bubenyák, B. Noszál, Kristóf Kóczián, Mária Takács, S. Béni, I. Hermecz, J. Kökösi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Bioisosteric replacements were accomplished by building the structural elements of piroxicam, an anti-inflammatory drug, into the pentacyclic system of rutaecarpine, a quinazolinocarboline alkaloid, in order to modify activity and selectivity on COX-isoenzymes. The pentacyclic compounds were synthesized efficiently by employing 1-oxo-9,10,11,12-tetrahydro-4H-pyrido[1,2-b]1,2-benzothiazine 5,5-dioxide as a key intermediate, and prepared by alternative routes. Condensation of the tricyclic ketone with arylhydrazines and subsequent Fischer-indolization provided the first representatives of new heterocyclic ring systems 3 and 4. Crown

Original languageEnglish
Pages (from-to)5711-5713
Number of pages3
JournalTetrahedron Letters
Volume49
Issue number40
DOIs
Publication statusPublished - Sep 29 2008

Fingerprint

Piroxicam
Ketones
Crowns
Alkaloids
Isoenzymes
Condensation
Anti-Inflammatory Agents
Pharmaceutical Preparations
rutecarpine
1,2-benzothiazine

Keywords

  • Alkaloid analogues
  • Anti-inflammatory drug
  • Bioisosteric hybrid
  • Piroxicam
  • Rutaecarpine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Bioisosteric hybrids of two anti-inflammatory agents, rutaecarpine and piroxicam. / Bubenyák, Máté; Noszál, B.; Kóczián, Kristóf; Takács, Mária; Béni, S.; Hermecz, I.; Kökösi, J.

In: Tetrahedron Letters, Vol. 49, No. 40, 29.09.2008, p. 5711-5713.

Research output: Contribution to journalArticle

Bubenyák, Máté ; Noszál, B. ; Kóczián, Kristóf ; Takács, Mária ; Béni, S. ; Hermecz, I. ; Kökösi, J. / Bioisosteric hybrids of two anti-inflammatory agents, rutaecarpine and piroxicam. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 40. pp. 5711-5713.
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