(Z,Z)- and (E,E)-4-androstene-3,17-dione dioxime | 5953-65-1

• 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: (Z,Z)- and (E,E)-4-androstene-3,17-dione dioxime
• 英文别名: androstene-(4)-dione-(3.17)-dioxime；Androsten-(4)-dion-(3.17)-dioxim；3,17-Dioxo-Δ⁴-androsten-dioxim；Androst-4-ene-3,17-dione, dioxime；N-[(8R,9S,10R,13S,14S)-3-hydroxyimino-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-ylidene]hydroxylamine
• CAS: 5953-65-1
• 化学式: C₁₉H₂₈N₂O₂
• 分子量: 316.444
• InChiKey: HDKWUWWSIDAZMQ-QAGGRKNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z,Z)- and (E,E)-4-androstene-3,17-dione dioxime 在 sodium 作用下， 以 丙醇 为溶剂， 生成 3β,17β-Diamino-Δ⁴-androsten
  参考文献：
  名称：

  Crabbe,P. et al., Bulletin des Societes Chimiques Belges, 1962, vol. 71, p. 203 - 216

  摘要：

  DOI：
• 作为产物：
  描述：

  雄烯二酮 在 盐酸羟胺 作用下， 以 水 为溶剂， 生成 (Z,Z)- and (E,E)-4-androstene-3,17-dione dioxime
  参考文献：
  名称：

  一滴化学衍生化-用于代谢物结构鉴定的DESI-MS分析

  摘要：

  代谢物的结构阐明是新药物开发和发现过程中的重要组成部分。液相色谱（LC）结合质谱（MS）通常是结构鉴定的首选技术，但不能始终提供所研究代谢物的精确结构鉴定（例如，羟基化位点和葡萄糖醛酸化位点）。为了鉴定这些代谢物，将不同的方法与MS数据结合使用，包括核磁共振，氢/氘交换和化学衍生化，然后进行LC-MS。这些技术通常很耗时，并且/或者需要额外的样品预处理。

  DOI：

  10.1002/jms.3604

文献信息

• Synthesis, Stereochemical Analysis, and Neuromuscular Blocking Activity of Selected E,E- and Z,Z-Isomeric O-Ethers of 4-Androstene-3,17-Dione Dioximes
  作者：David B. Garcia、Robert G. Brown、Jaime N. Delgado

  DOI：10.1002/jps.2600690903

  日期：1980.9

  A number of selected geometric oxime ethers were synthesized as potential neuromuscular blocking agents. The study consisted of the synthesis, separation, and stereochemical analysis of selected compounds followed by a preliminary pharmacological evaluation for neuromuscular blockade. Synthesis of the compounds began with the double oximination of 4-androstene-3,17-dione followed by TLC, column chromatography

  合成了许多选定的几何肟醚作为潜在的神经肌肉阻滞剂。该研究包括所选化合物的合成，分离和立体化学分析，然后进行神经肌肉阻滞剂的初步药理评估。化合物的合成开始于4-雄烯3,17-二酮的双氧化，然后用薄层色谱，柱色谱和分步结晶作为纯化方法。这些步骤产生了可能的四种异构体中的两种。分离对上的构型分配基于使用IR，UV和NMR光谱的实验。异构体纯的二醚是通过两种方法制备的：（a）用适当的氨基烷基卤化物将立体化学纯的二肟进行O-烷基化，（b）二肟混合物的O-烷基化，然后进行季铵化，随后通过分步结晶分离出构型纯的盐。通过在跑步机上使用小鼠进行初步的药理评估。讨论了一些结构-活动关系。
• REGENERATION OF STEROID KETONES FROM THEIR SEMICARBAZONES WITH PYRUVIC ACID¹
  作者：E. B. HERSHBERG

  DOI：10.1021/jo01162a011

  日期：1948.7
• Convenient preparation of A-ring fused pyridines from steroidal enamides
  作者：Madan G. Barthakur、Moyurima Borthakur、Romesh C. Boruah

  DOI：10.1016/j.steroids.2008.04.016

  日期：2008.10

  A facile strategy for the preparation of A-ring fused pyridosteroids has been accomplished in high yields by the reaction of Vilsmeier reagent (chloromethyleneiminium salt) with steroidal A-ring enamides (2- and 3-ene) under thermal conditions. The structure of 6'-chloro-5 alpha-cholest [3,2-b]pyridine was determined by X-ray analysis. (c) 2008 Elsevier Inc. All rights reserved.
• Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: A screening approach to detect forbidden treatments
  作者：Patricia Regal、Carolina Nebot、Mónica Díaz-Bao、Rocio Barreiro、Alberto Cepeda、Cristina Fente

  DOI：10.1016/j.steroids.2010.12.005

  日期：2011.3

  Estradiol benzoate (EB) has been one of the most widely used estrogenic agents in animal husbandry, as a way of exogenously introducing the natural hormone estradiol-17 beta into the animal organism. Estradiol was previously employed to induce anabolic effects or reproductive improvements in cattle. However, the employment of EB in European countries has been permanently forbidden by Directive 2008/97/EC to guarantee consumers' health. Despite this prohibition, the control of estradiol-17 beta and its esters continues to be a difficult task for residue-monitoring plans in European Communities because official analyses of natural thresholds for hormones in cattle have not yet been established, leading to a lack of confirmation for any exogenous administration of natural hormones. Several researchers have worked on excretion profiles of metabolites, variation in specific hormonal ratios and metabolomic fingerprints after hormonal treatments. This research focuses on the possible existence of disturbances in the serum profile of animals treated with EB in terms of steroid sex hormones (androgens, oestrogens and progestogens), by investigating the serum levels of several of these hormones. The serum samples were collected from three groups of cows: one treated with an intramuscular injection of EB, one treated with a combination of intravaginal EB and progesterone and a control (non-treated) group. The samples have been analysed by a validated high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method, and 17 natural hormones were identified and quantified. Subsequently, data from the serum profiles were submitted for statistic and multivariate analysis, and it was possible to observe a manifest variation between animal groups. The obtained results can help in the development of a viable screening tool for monitoring purposes in cattle. (C) 2010 Elsevier Inc. All rights reserved.