3-<(N,N-dimethylthiocarbamoyl)oxy>estra-1,3,5(10)-trien-17-one | 13522-76-4

• 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: 3-<(N,N-dimethylthiocarbamoyl)oxy>estra-1,3,5(10)-trien-17-one
• 英文别名: 3--estran-17-on；O-[[(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]] N,N-dimethylcarbamothioate
• CAS: 13522-76-4
• 化学式: C₂₁H₂₇NO₂S
• 分子量: 357.517
• InChiKey: LYJMSUZAFPBCJV-WIRSXHRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<(N,N-dimethylthiocarbamoyl)oxy>estra-1,3,5(10)-trien-17-one 在 titanium(IV) dioxide 作用下， 以 二氯甲烷 为溶剂， 以20 %的产率得到3-<(N,N-dimethylcarbamoyl)thio>estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  温和条件下多相光催化实现阳离子自由基纽曼-夸特重排

  摘要：

  TiO 2催化的光化学重排：苯硫酚的常用合成路线涉及O-芳基硫代氨基甲酸酯的O - S重排作为关键步骤。由于高反应温度（200 – 300 °C）和伴随的选择性问题，重排代表了序列的瓶颈。在这种情况下，我们提出了一种使用廉价的 TiO 2作为光催化剂的温和光催化方法。

  DOI：

  10.1002/cctc.202300744
• 作为产物：
  描述：

  雌酚酮 、 二甲氨基硫代甲酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以87%的产率得到3-<(N,N-dimethylthiocarbamoyl)oxy>estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Synthesis and biochemical studies of estrone sulfatase inhibitors

  摘要：

  The synthesis and biochemical evaluation of estrone sulfatase inhibitors are described. Inhibitors were designed through modifications of the substrate estrone sulfate. An in vitro assay using the microsomal fraction isolated from human term placenta was used to evaluate sulfatase inhibitory activity. All the inhibitors (except sulfonyl chloride analog) exhibited low inhibitory activities in the screening assay. Sulfonyl chloride analog is a strong inhibitor, which caused 91.5% inhibition of the enzymatic activity at 300 microM.

  DOI：

  10.1016/0039-128x(93)90045-o

文献信息

• The Conversion of Phenols to Thiophenols via Dialkylthiocarbamates¹
  作者：Melvin S. Newman、Harold A. Karnes

  DOI：10.1021/jo01350a023

  日期：1966.12
• Sulphonic acid substituted aromatic steroids as inhibitors of steroid 5-alpha-reductase
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0375347B1

  公开（公告）日：1994-12-21
• US4970205A
  申请人：——

  公开号：US4970205A

  公开（公告）日：1990-11-13
• Synthesis and biochemical studies of estrone sulfatase inhibitors
  作者：Pui-Kai Li、Radhakrishnan Pillai、Barry L. Young、William H. Bender、Dino M. Martino、Fu-Tyan Lin

  DOI：10.1016/0039-128x(93)90045-o

  日期：1993.3

  The synthesis and biochemical evaluation of estrone sulfatase inhibitors are described. Inhibitors were designed through modifications of the substrate estrone sulfate. An in vitro assay using the microsomal fraction isolated from human term placenta was used to evaluate sulfatase inhibitory activity. All the inhibitors (except sulfonyl chloride analog) exhibited low inhibitory activities in the screening assay. Sulfonyl chloride analog is a strong inhibitor, which caused 91.5% inhibition of the enzymatic activity at 300 microM.