6β,7β,15β,16β-dimethylene-3-oxo-11α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone | 95218-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 6β,7β,15β,16β-dimethylene-3-oxo-11α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone
• 英文别名: 6β,7β:15β,16β-dimethylene-11α-hydroxy-3-oxo-17α-pregn-4-ene-21,17-carbolactone；6β,7β,15β,16β-dimethylene-11α-hydroxy-3-oxo-17α-pregn-4-en-21,17-carbolactone；(1S,2R,4R,10R,11S,12R,14S,15S,16S,18S,19S)-12-hydroxy-10,14-dimethylspiro[hexacyclo[9.8.0.02,4.05,10.014,19.016,18]nonadec-5-ene-15,5'-oxolane]-2',7-dione
• CAS: 95218-07-8
• 化学式: C₂₄H₃₀O₄
• 分子量: 382.5
• InChiKey: OEMKUEDWDSBGFI-BTZBBTJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  屈螺酮 以27.6%的产率得到6β,7β,15β,16β-dimethylene-3-oxo-11α-dihydroxy-17α-pregn-4-ene-21,17-carbolactone
  参考文献：
  名称：

  醛固酮拮抗剂。1. 6 beta，7 beta：15 beta，16 beta-二亚甲基甾体螺内酯的合成及活性。

  摘要：

  合成了高活性醛固酮拮抗剂dihydrospirorenone（2）和spirorenone（3）的几种衍生物。这些努力的目的是制备表现出降低的内分泌特性的化合物，其醛固酮的拮抗活性与螺旋体酮相同或更好。1α，2α-亚甲基衍生物20与螺旋体酮相比具有相似的醛固酮拮抗效力，但是未显示出减少的内分泌副作用。化合物4-11、15-19和21中的其他取代基分别急剧降低了醛固酮拮抗活性2或3。

  DOI：

  10.1021/jm50001a002

文献信息

• New metabolites of drospirenone obtained in Mucorales fungi culture
  作者：Paula G. Quintana、Stella M. Romero、Graciela Vaamonde、Alicia Baldessari

  DOI：10.1016/j.molcatb.2013.08.005

  日期：2013.12

  Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2,17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus wyzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6 beta,7 beta,15 beta,16 beta-dimethylene-11ce-hydroxy3-oxo-17 alpha-pregn-4-en-21,17-carbolactone (2), 6 beta,7 beta,15 beta,16 beta-dimethylene-11 alpha-hydroxy-3-oxo-17 beta-pregn-4-en-21,17-carbolactone (3), 6 beta,7 beta,15 beta,16 beta-dimethylene-11 beta-hydroxy-3-oxo-17a-pregn-4-en-21,17-carbolactone (4) and 6 beta,7 beta,15 beta,16 beta-dimethylene-2 beta-hydroxy-3-oxo-17a-pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process. 2013 Elsevier B.V. All rights reserved.