Synthesis of a novel dicyano abietane analogue: a potential antiinflammatory agent.
From a structure-activity relationship perspective, the new abietane 5 having cyano groups at C-2 and C-13 and a phenolic ring C has been synthesized and evaluated biologically because the related compound 4 has high potency in inflammation models in vitro and in vivo. Compound 5 was synthesized from 8, which was obtained in five steps from the known compound 9, via an unexpected aromatization caused by the addition of PhSeCl and subsequent oxidation/elimination of the selenated intermediate 14 with H2O2.
Honda
Tadashi
T
Department of Chemistry, Dartmouth College, 6128 Burke Laboratory, Hanover, New Hampshire 03755, USA. th9@dartmouth.edu
Yoshizawa
Hidenori
H
Sundararajan
Chitra
C
Gribble
Gordon W
GW
D045784:Abietanes / Q000138:chemical synthesis* / Q000737:chemistry; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
D045784:Abietanes; D000893:Anti-Inflammatory Agents; D009570:Nitriles