3E-oximino-4-androsten-17β-yl acetate | 21238-86-8

• 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: 3E-oximino-4-androsten-17β-yl acetate
• 英文别名: syn-testosterone-17-acetate oxime；anti-17β-Acetoxy-3-oxyimino-4-androsten；[(3E,8R,9S,10R,13S,14S,17S)-3-hydroxyimino-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 21238-86-8
• 化学式: C₂₁H₃₁NO₃
• 分子量: 345.482
• InChiKey: HMPWCNANWMGWIQ-YWVIAJDESA-N

物化性质

• 沸点：
  473.5±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3E-oximino-4-androsten-17β-yl acetate 、 N-(2-氯乙基)吡咯烷盐酸盐 在 氢氧化钾 、 potassium carbonate 作用下， 以 丁酮 为溶剂， 反应 48.0h， 生成 3E-[O-(2-pyrrolidinoethyl)]oximino-4-androsten-17β-ol
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 2-alkylaminoethyl derivatives of various steroidal oximes

  摘要：

  Various steroidal oxime ether I derivatives in androstene and estrane series have been synthesized and evaluated for the antineoplastic activity at National Cancer Institute, Bethesda, Maryland, USA. O-Alkylation of the oximes by various alkylaminoethyl halides gave the oxime ether derivatives. The 17alpha-ethynylandrostene derivatives 29 (DPJ-684), 30 (DPJ-685), 31 (DPJ-686) and estrane derivatives 35 (DPJ-531) and 36 (DPJ-532) were among the small percentage of compounds, which have been screened by NCI for in vivo hollow fiber assay by virtue of their activity against one or more human tumour cell lines in 60 cell line in vitro prescreen. The preliminary in vivo reports of hollow fiber assays have been referred to the Biological Evaluation Committee for Cancer Drugs for considering these, compounds for further detailed in vivo testing. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.09.002
• 作为产物：
  描述：

  醋酸睾酮 在 吡啶 、 盐酸羟胺 、 水 作用下， 生成 3E-oximino-4-androsten-17β-yl acetate
  参考文献：
  名称：

  Synthesis and antineoplastic activity of 2-alkylaminoethyl derivatives of various steroidal oximes

  摘要：

  Various steroidal oxime ether I derivatives in androstene and estrane series have been synthesized and evaluated for the antineoplastic activity at National Cancer Institute, Bethesda, Maryland, USA. O-Alkylation of the oximes by various alkylaminoethyl halides gave the oxime ether derivatives. The 17alpha-ethynylandrostene derivatives 29 (DPJ-684), 30 (DPJ-685), 31 (DPJ-686) and estrane derivatives 35 (DPJ-531) and 36 (DPJ-532) were among the small percentage of compounds, which have been screened by NCI for in vivo hollow fiber assay by virtue of their activity against one or more human tumour cell lines in 60 cell line in vitro prescreen. The preliminary in vivo reports of hollow fiber assays have been referred to the Biological Evaluation Committee for Cancer Drugs for considering these, compounds for further detailed in vivo testing. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.09.002

文献信息

• Beckmann rearrangement of 3-aza-a-homo-4α-androsten-4,17-dione oxime and 3-oxo-13α-amino-13,17-seco-4-androsten-17-oic 13,17-lactam oxime
  作者：Charalabos Camoutsis、Panayotis Catsoulacos

  DOI：10.1002/jhet.5570200449

  日期：1983.7

  Rearrangements of 3-aza-A-homo-4α-androsten-4, 17-dione oxime produced a mixture of the normal lactam product and the product of a “second order” cleavage, an unsaturated nitrile. The lactam 3, 17α-di-aza-A, D-bishomoandrost-4α-ene-4, 17-dione was also obtained from the rearrangement of the syn-3-oxo-13α-amino-13, 17-seco-4-androsten-17-oic-13, 17-lactam oxime. The resolution of syn- and anti-isomers

  3-氮杂-A-homo-4α-androsten-4、17-二酮肟的重排产生了正常内酰胺产物和“二级”裂解产物（不饱和腈）的混合物。内酰胺3，17α-di-氮杂-A，D-比绍莫雄罗斯-4α-ene-4，17-二酮也可以通过重新排列syn -3-oxo-13α-amino-13，17-seco-4获得-androsten-17-oic-13、17-内酰胺肟。的分辨率顺和反VIII的异构体通过柱色谱法来实现和它们的结构由光谱数据确定。
• Synthesis and evaluation of new steroidal lactam conjugates with aniline mustards as potential antileukemic therapeutics
  作者：Dimitrios Trafalis、Elena Geromichalou、Panagiotis Dalezis、Nikolaos Nikoleousakos、Vasiliki Sarli

  DOI：10.1016/j.steroids.2016.07.009

  日期：2016.11

  Alkylating agents are still nowadays one of the most important classes of cytotoxic drugs, which display a wide range of therapeutic use for the treatment of various cancers. We have synthesized and tested four hybrid homo-azasteroidal alkylating esters for antileukemic activity against five sensitive to alkylating agents human leukemia cell lines in vitro and against P388 murine leukemia in vivo.

  如今，烷基化剂仍然是最重要的细胞毒性药物之一，其显示出广泛的治疗用途，可用于治疗各种癌症。我们已经合成和测试了四种杂合的氮杂氮杂甾类烷基化酯，它们对五种对烷基化剂，人白血病细胞系体外敏感，以及对P388鼠类白血病的体内抗白血病活性具有抗白血病作用。比较地，还研究了美法仑和3-（4-（双（2-氯乙基）氨基）苯氧基）丙酸（POPAM）。在体外和体内，所有的均氮-氮杂-甾族烷烃都显示出较低的急性毒性，非常有希望的抗白血病活性。