TY - JOUR
T1 - Synthetic and Enzymatic Studies with Potential Alternate Substrates for Human Placental Aromatase
T2 - 10β-Trifluoroacetyl and 10β-allyl Steroids
AU - Jaworski, Krysztof
AU - Cole, Philip A.
AU - Robinson, Cecil H.
PY - 1993/9
Y1 - 1993/9
N2 - The l0β-trifiuoroacetyl and 10β-allyl analogs, 6 and 13, respectively, of androstenedione have been studied as potential alternate substrates for aromatase. The hitherto undescribed compound 6 was synthesized via the action of trifluoromethyltrimethylsilane on a 19-oxo steroid. There was no conversion of 6 to estrogen by aromatase, although 6 was a competitive inhibitor. Furthermore 13 was not epoxidized significantly by the enzyme, leaving open the mechanism of suicide inactivation of aromatase by the propargylic steroid 10.
AB - The l0β-trifiuoroacetyl and 10β-allyl analogs, 6 and 13, respectively, of androstenedione have been studied as potential alternate substrates for aromatase. The hitherto undescribed compound 6 was synthesized via the action of trifluoromethyltrimethylsilane on a 19-oxo steroid. There was no conversion of 6 to estrogen by aromatase, although 6 was a competitive inhibitor. Furthermore 13 was not epoxidized significantly by the enzyme, leaving open the mechanism of suicide inactivation of aromatase by the propargylic steroid 10.
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U2 - 10.1006/bioo.1993.1028
DO - 10.1006/bioo.1993.1028
M3 - Article
AN - SCOPUS:0027424425
SN - 0045-2068
VL - 21
SP - 330
EP - 341
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
IS - 3
ER -