Syntheses of immunomodulating androstanes and stigmastanes: comparison of their TNF-alpha inhibitory activity.
In a previous work our group showed that some synthetic stigmastanes may play a role in immune-mediated inflammation. In this paper we report the syntheses of a series of new steroidal compounds derived from dehydroepiandrosterone and stigmasterol, and the evaluation of their in vitro inhibitory activity of the TNF-alpha production by macrophages. A preliminary qualitative structure-activity relationship was established.
Ramírez
Javier A
JA
Departamento de Química Orgánica and UMYMFOR (CONICET-Facultad de Ciencias Exactas y Naturales), Universidad de Buenos Aires, Pabellón 2, Piso 3, Ciudad Universitaria, C1428EGA, Buenos Aires, Argentina.
Bruttomesso
Andrea C
AC
Michelini
Flavia M
FM
Acebedo
Sofía L
SL
Alché
Laura E
LE
Galagovsky
Lydia R
LR
D000731:Androstanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002460:Cell Line; D002776:Cholestanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003687:Dehydroepiandrosterone / Q000737:chemistry; D004353:Drug Evaluation, Preclinical; D007155:Immunologic Factors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D051379:Mice; D015394:Molecular Structure; D013265:Stigmasterol / Q000737:chemistry; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors*
D000731:Androstanes; D002776:Cholestanes; D007155:Immunologic Factors; D014409:Tumor Necrosis Factor-alpha; D003687:Dehydroepiandrosterone; D013265:Stigmasterol