Chinn L J, Brown E A, Mizuba S S, Karim A
J Med Chem. 1977 Mar;20(3):352-5. doi: 10.1021/jm00213a008.
15alpha-Hydroxycanrenone (1b) was prepared from canrenone (1a) by microbiological oxidation with a penicillium species. The product was identical with one obtained from the metabolism of spironolactone(3) in human. Oxidation of 1b with Jones regent furnished the corresponding 15-oxocanrenone (1d) which underwent base-catalyzed beta elimination to generate an alpha,beta-unsaturated cyclopentenone system. 15alpha-Hydroxycanrenone (1b) failed to show antimineralocorticoid activity at the screening dose of 2.4 mg while the oxo derivative 1d exhibited approximately 15% the activity of 3. Since the activity of canrenone is 38% that of spironolactone, introduction of the carbonyl group at the 15 position of canrenone resulted in a reduction in activity. This effect is opposite to that observed with 6-dehydroprogesterone.
15α-羟基坎利酮（1b）由坎利酮（1a）通过青霉菌进行微生物氧化制备而成。该产物与人体内螺内酯（3）代谢产生的产物相同。用琼斯试剂氧化1b得到相应的15-氧代坎利酮（1d），其在碱催化下发生β消除反应，生成α,β-不饱和环戊烯酮体系。15α-羟基坎利酮（1b）在2.4毫克的筛选剂量下未表现出抗盐皮质激素活性，而氧代衍生物1d的活性约为3的15%。由于坎利酮的活性为螺内酯的38%，在坎利酮的15位引入羰基会导致活性降低。这种效应与6-脱氢孕酮所观察到的相反。
