Structure-activity relationship study of androstene steroids with respect to local anti-inflammatory activity.
A sex hormone, 3beta-acetoxy-17beta-hydroxy-androst-5-ene (1) (CAS 1639-43-6), was isolated from aerial parts of Acacia nilotica. This compound is reported to have anti-inflammatory activity. In view of this, considering this molecule as a lead molecule different androstene compounds were synthesized to study their potency and structure-activity relationship with respect to local anti-inflammatory activity. The experiments indicated that 17 ketonic compounds were more active towards inflammation than their oxime analogues. Similarly, for the compounds containing an acetyl group fixed at C-3 position a decreasing trend of activity was observed in the order of ketonic, hydroxyl, oxime and acetyl group, respectively, when these groups are at C-17 position.
Chaubal
Rohini
R
T. R. Ingle Research Laboratory, Department of Chemistry, Sir Parshurambhau College, Pune, India.
Mujumdar
Arvind M
AM
Misar
Ashwini
A
Deshpande
Vishnu H
VH
Deshpande
Nirmala R
NR
D000736:Androstenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004431:Ear, External / Q000473:pathology; D004487:Edema / Q000139:chemically induced / Q000473:pathology / Q000517:prevention & control; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship
D000736:Androstenes; D000893:Anti-Inflammatory Agents