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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis of two new hydroxylated derivatives of spironolactone by microbial transformation
Jianfeng Mei1, Luoyi Wang2, Siyuan Wang2
1Department of Biological Engineering, Utah State University, 4105 Old Main Hill, Logan, UT 84322, United States; College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, Zhejiang 310032, China.
Abstract:
Spironolactone is a medicinally important molecule that is clinically used in the treatment and management of many diseases such as oedema and ascites in cirrhosis of the liver, malignant ascites, nephrotic syndrome, chronic lung disease, resistant hypertension, congestive heart failure, and primary hyperaldosteronism. Microbial transformations of spironolactone by Cunninghamella elegans ATCC 9245 was carried out. Two new hydroxylated derivatives, 12β-hydroxy-spironolactone and 2α-hydroxy-spironolactone, were synthesized. Their structures were characterized on the basis of the spectroscopic data. The substrate can be efficiently converted into the products within 72 h after its addition to the fermentation broth of C. elegans ATCC 9245.
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