Synthesis and evaluation of the analgesic and antiinflammatory activities of O-substituted salicylamides

Arch Pharm Res. 2001 Jun;24(3):171-9. doi: 10.1007/BF02978252.

Abstract

The present investigation deals with the synthesis of some new salicylamidoacetyl sulfonamides 3a,b, salicylamido ethylacetate 4, salicylamido acetic acid hydrazide 5, which is considered as the key intermediate for the synthesis of several series of new compounds such as salicylamido pyrazol 6 and pyrazolone 7. N-imido-derivatives 9, 10, 11, thiadiazole 13, oxadiazole 14, 15, Schiffs bases 16a-f. Cyclocondensation of Schiffs bases with thioglycolic acid gave thiazolidinone 18a-c while with acetylchloride afforded azitidinones 19a-c and with acetic anhydride gave 1,4-benzoxazepine-3,5-dione. Some of the compounds were tested for their analgesic and antiinflammatory activities as well as ulcerogenic effects. Some derivatives were more effective than salicylamide and ulcerogenic activity was variably lowered.

MeSH terms

  • Analgesics, Non-Narcotic / chemical synthesis*
  • Analgesics, Non-Narcotic / pharmacology*
  • Analgesics, Non-Narcotic / toxicity
  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Anti-Inflammatory Agents, Non-Steroidal / toxicity
  • Carrageenan
  • Edema / chemically induced
  • Edema / prevention & control
  • Electric Stimulation
  • Indicators and Reagents
  • Male
  • Pleurisy / chemically induced
  • Pleurisy / prevention & control
  • Rats
  • Salicylamides / chemical synthesis*
  • Salicylamides / pharmacology*
  • Salicylamides / toxicity
  • Stomach Ulcer / chemically induced
  • Stomach Ulcer / pathology
  • Structure-Activity Relationship

Substances

  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents, Non-Steroidal
  • Indicators and Reagents
  • Salicylamides
  • Carrageenan