trimegestone | 74525-67-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: trimegestone
• 英文别名: 17α-methyl-17β-(2-(R)-hydroxy-1-oxopropyl)-estra-4,9-dien-3-one；RU27987；(8S,13S,14S,17S)-17-[(2R)-2-hydroxypropanoyl]-13,17-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 74525-67-0
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: JUNDJWOLDSCTFK-PWGGLJECSA-N

物化性质

• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trimegestone 在 Mucor hiemalis BO 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以63%的产率得到11β-hydroxytrimegestone
  参考文献：
  名称：

  Microbial models of drug metabolism: microbial transformations of trimegestone® (RU27987), a 3-Keto-Δ4,9(10)-19-norsteroid drug

  摘要：

  Screening microorganisms for the biotransformation of the 3-keto-Delta(4.9(10))-19-norsteroid RU27987 (Trimegestone(R)) resulted in the isolation of nine identified metabolites, some of them being selectively produced by different strains. Eight metabolites were found to be hydroxylated on various positions of the rings, and one was additionally epoxidized. These microbial metabolites could be used as chromatographic standards and two of them were found identical to the unknown major human metabolites, Moreover, most microbial metabolites were produced in sufficient amounts to be tested for their biological activities. All these features demonstrate the usefulness and versatility of microbial biotransformation systems as a tool for early identification and convenient production of potentially active mammalian and non-mammalian metabolites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00179-0
• 作为产物：
  描述：

  17α-methyl-17β-(1,2-dioxopropyl)-estra-4,9-dien-3-one 在 Pt{Sn}0.5*hydrocinchonidine 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、8.11 MPa 条件下， 以55%的产率得到曲美孕酮
  参考文献：
  名称：

  负载的类固醇上的氧化石棉的化学，区域和非对映选择性加氢成三甲基硅石：过渡金属，载体性质，锡添加剂和改性剂的影响

  摘要：

  将氧代孕酮（17α-甲基-17β-（1,2-二氧丙基）-estra-4,9-dien-3-one）1选择性加氢成三聚氰胺（17α-甲基-17β-（2（S）-在各种单金属催化剂上进行羟基2-氧代丙基）-estra-4，9-dien-3-one）2的反应。活性顺序，Pd> Rh> Pt> Ir> Os，几乎与化学选择性相反（羰基相对于内部烯烃双键的选择性氢化），Os> Ir> Pt = Pd> Rh。没有金属给出任何所需的非对映选择性（21（S）-OH醇的选择性形成）。然而，二氧化硅负载的铑，钯和铂对于C 3羰基的氢化显示出100％的非对映异构体过量（de）。铂/二氧化硅2催化剂表现出低的化学选择性（24％），但是其TON活性相对较高（42×10 -3 s -1）。铂小号{锡} ñ /二氧化硅2种催化剂，由SN（CH的相互作用制备3）4具有减少的Pt /二氧化硅2在H 2在室温下，表现出比的Pt

  DOI：

  10.1006/jcat.1999.2760

文献信息

• POMPER, MARTIN G.;PINNEY, KEVIN G.;CARLSON, KATHRYN E.;VAN, BROCKLIN HENR+, NUCL. MED. AND BIOL., 17,(1990) N, C. 309-319
  作者：POMPER, MARTIN G.、PINNEY, KEVIN G.、CARLSON, KATHRYN E.、VAN, BROCKLIN HENR+

  DOI：——

  日期：——
• Chemo-, Regio-, and Diastereoselective Hydrogenation of Oxopromegestone into Trimegestone over Supported Platinoids: Effects of the Transition Metal, Support Nature, Tin Additives, and Modifiers
  作者：Yurii A. Ryndin、Catherine C. Santini、Denis Prat、Jean Marie Basset

  DOI：10.1006/jcat.1999.2760

  日期：2000.3

  The selective hydrogenation of oxopromegestone (17α-methyl-17β-(1,2-dioxopropyl)-estra-4,9-dien-3-one), 1, into Trimegestone (17α-methyl-17β-(2(S)-hydroxy-1-oxopropyl)-estra-4,9-dien-3-one), 2, was carried out on various monometallic catalysts. The order of activity, Pd>Rh>Pt>Ir>Os, was almost opposite that of the chemoselectivity (selective hydrogenation of the carbonyl versus the internal olefinic

  将氧代孕酮（17α-甲基-17β-（1,2-二氧丙基）-estra-4,9-dien-3-one）1选择性加氢成三聚氰胺（17α-甲基-17β-（2（S）-在各种单金属催化剂上进行羟基2-氧代丙基）-estra-4，9-dien-3-one）2的反应。活性顺序，Pd> Rh> Pt> Ir> Os，几乎与化学选择性相反（羰基相对于内部烯烃双键的选择性氢化），Os> Ir> Pt = Pd> Rh。没有金属给出任何所需的非对映选择性（21（S）-OH醇的选择性形成）。然而，二氧化硅负载的铑，钯和铂对于C 3羰基的氢化显示出100％的非对映异构体过量（de）。铂/二氧化硅2催化剂表现出低的化学选择性（24％），但是其TON活性相对较高（42×10 -3 s -1）。铂小号锡} ñ /二氧化硅2种催化剂，由SN（CH的相互作用制备3）4具有减少的Pt /二氧化硅2在H 2在室温下，表现出比的Pt
• Microbial models of drug metabolism: microbial transformations of trimegestone® (RU27987), a 3-Keto-Δ4,9(10)-19-norsteroid drug
  作者：Isabelle Lacroix、Jacques Biton、Robert Azerad

  DOI：10.1016/s0968-0896(99)00179-0

  日期：1999.11

  Screening microorganisms for the biotransformation of the 3-keto-Delta(4.9(10))-19-norsteroid RU27987 (Trimegestone(R)) resulted in the isolation of nine identified metabolites, some of them being selectively produced by different strains. Eight metabolites were found to be hydroxylated on various positions of the rings, and one was additionally epoxidized. These microbial metabolites could be used as chromatographic standards and two of them were found identical to the unknown major human metabolites, Moreover, most microbial metabolites were produced in sufficient amounts to be tested for their biological activities. All these features demonstrate the usefulness and versatility of microbial biotransformation systems as a tool for early identification and convenient production of potentially active mammalian and non-mammalian metabolites. (C) 1999 Elsevier Science Ltd. All rights reserved.