Studies on anti-ulcer agents. II. Synthesis and anti-ulcer activities of 6-isopropylazulene-1-sodium sulfonate derivatives

Chem Pharm Bull (Tokyo). 1990 Dec;38(12):3355-8. doi: 10.1248/cpb.38.3355.

Abstract

A series of alkylazulene-1-sodium sulfonate derivatives which has an isopropyl group at 6-position were synthesized, and their anti-ulcer activities were examined in Shay pylorus-ligated rats. The values of lipophilicity (log P) as a parameter of these new azulene derivatives were also examined in reference to the structure-activity relationship. The optimum value of log P, which showed maximal anti-ulcer activity, was about -0.46. Among the derivatives of azulene examined, 3-ethyl-6-isopropylazulene-1-sodium sulfonate (compound IXb:XT1-785) exhibited the most potent inhibitory action against Shay ulcer, and its anti-peptic activity was similar to that of 3-ethyl-7-isopropylazulene-1-sodium sulfonate (KT1-32). It also had more activity than guaiazulene sodium sulfonate (GAS). Furthermore, KT1-785 was extremely stable under heating as compared to GAS.

MeSH terms

  • Animals
  • Anti-Ulcer Agents / chemical synthesis*
  • Arylsulfonates / chemical synthesis*
  • Arylsulfonates / pharmacology
  • Cycloheptanes / chemical synthesis*
  • Cycloheptanes / pharmacology
  • Male
  • Pepsin A / antagonists & inhibitors
  • Rats
  • Rats, Inbred Strains
  • Structure-Activity Relationship

Substances

  • Anti-Ulcer Agents
  • Arylsulfonates
  • Cycloheptanes
  • Pepsin A