17α-hydroxy-4-estren-3-one | 4409-34-1

• 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: 17α-hydroxy-4-estren-3-one
• 英文别名: 17α-hydroxyestr-4-en-3-one；17α-19-nortestosterone；norepitestosterone；17α-nandrolone；epinandrolone；(8R,9S,10R,13S,14S,17R)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 4409-34-1
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: NPAGDVCDWIYMMC-SHRADXDESA-N

物化性质

• 熔点：
  146-149 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• 沸点：
  434.5±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17α-hydroxy-4-estren-3-one 生成 11beta-Hydroxyestrone
  参考文献：
  名称：

  PETZOLDT, K.;NEEF, G.;EDER, U.

  摘要：

  DOI：
• 作为产物：
  描述：

  诺龙 在 二苯基-2-吡啶膦 、 偶氮二甲酸二异丙酯 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 17α-hydroxy-4-estren-3-one
  参考文献：
  名称：

  Easy stereoselective synthesis of 5α-estrane-3β,17α-diol, the major metabolite of nandrolone in the horse

  摘要：

  5 alpha-Estrane-3 beta,17 alpha-diol is the major metabolite of nandrolone in horse urine. The presence of 5 alpha-estrane-3 beta,17 alpha-diol in female and gelding urines is prohibited by Racing Rules and its natural presence in male urine led regulation authorities to establish a concentration threshold of 45 ng/mL. This paper describes a rapid, simple and stereoselective synthesis of 5 alpha-estrane-3 beta,17 alpha-diol, providing horseracing laboratories with an essential reference material for their antidoping performance. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.03.004

文献信息

• Stereocontrolled synthesis of the four 16-hydroxymethyl-19-nortestosterone isomers and their antiproliferative activities
  作者：Gyula Schneider、Anita Kiss、Erzsébet Mernyák、Zsanett Benke、János Wölfling、Éva Frank、Noémi Bózsity、András Gyovai、Renáta Minorics、István Zupkó

  DOI：10.1016/j.steroids.2015.12.003

  日期：2016.1

  Novel 16-hydroxymethyl-19-nortestosterone diastereomers were prepared by Birch reduction from the corresponding 3-methoxy-16-hydroxymethylestra-1,3,5(10)-trien-17-ol isomers with known configurations. The synthesized compounds are 16 alpha- and 16 beta-hydroxymethyl-substituted 19-nortestosterone and their 17 alpha-epimers. To prepare 17 alpha-19-nortestosterone, the Mitsunobu inversion reaction of 19-nortestosterone with different alkyl and aryl carboxylic acids was chosen. Deacylation of the new compounds by the Zemplen method yielded the required 17 alpha-19-nortestosterone.The antiproliferative activities of the structurally related compounds were determined in vitro through microculture tetrazolium assays on a panel of human adherent cervical (HeLa, SiHa and C33A), breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) and ovarian (A2780) cell lines. The 17 alpha epimer of 19-nortestosterone demonstrated considerable activity, selectively for HeLa cells, with a calculated IC50 of 0.65 mu M. The reference compound, cisplatin, displayed an order of magnitude higher IC50 (12.4 mu M). The cancer selectivity of 17 alpha-19-nortestosterone was tested by MTT assay performed with noncancerous human fibroblast cell line MRC-5. The results indicated that 17 alpha-19-nortestosterone selectively disturbs the viability of HeLa cells without greatly affecting other cancer cell types and intact fibroblasts. (C) 2015 Elsevier Inc. All rights reserved.
• In vitro inhibitory effects of 16-methyl-substituted steroids on 5α-reductase in rat and human prostates
  作者：Imre Faredin、István Tóth、János Wölfling、Gyula Schneider、Eszter Meskó

  DOI：10.1016/0039-128x(94)90049-3

  日期：1994.10

  The inhibitory effects (IC50) of 16-methyl steroids on 5 alpha-reductase were studied. The in vitro experiments were carried out with homogenates of rat and human prostates. The investigated 16-methyl steroids were found to be weak inhibitors. In comparison with the known 5 alpha-reductase inhibitor 4-MA (17 beta-N, N-diethylcarbamol-4-methyl-4-aza-5 alpha-androstan-3-one), the relative IC50 values of the studied compounds are 4.7 times or more greater than 4-MA in human prostate and 23.5 times or more greater than 4-MA in rat prostate. The IC50 values increase in the sequence 16 alpha-, 16 beta- and 16,16-dimethyl derivatives. In human prostate homogenates IC50 caries between 0.6 and 120, while in rat it ranges from 1.6 to 1000 mu M. This shows that the enzyme of the human prostate is more sensitive than that of the rat prostate to the methyl-substituted compounds.
• Easy stereoselective synthesis of 5α-estrane-3β,17α-diol, the major metabolite of nandrolone in the horse
  作者：Frédéric Balssa、Michael Fischer、Yves Bonnaire

  DOI：10.1016/j.steroids.2011.03.004

  日期：2011.6

  5 alpha-Estrane-3 beta,17 alpha-diol is the major metabolite of nandrolone in horse urine. The presence of 5 alpha-estrane-3 beta,17 alpha-diol in female and gelding urines is prohibited by Racing Rules and its natural presence in male urine led regulation authorities to establish a concentration threshold of 45 ng/mL. This paper describes a rapid, simple and stereoselective synthesis of 5 alpha-estrane-3 beta,17 alpha-diol, providing horseracing laboratories with an essential reference material for their antidoping performance. (C) 2011 Elsevier Inc. All rights reserved.
• PETZOLDT, K.;NEEF, G.;EDER, U.
  作者：PETZOLDT, K.、NEEF, G.、EDER, U.

  DOI：——

  日期：——