(6E)-hydroximinocholest-4-en-3β-ol | 110556-49-5

• 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: (6E)-hydroximinocholest-4-en-3β-ol
• 英文别名: (3S,6E,8S,9S,10R,13R,14S,17R)-6-hydroxyimino-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 110556-49-5
• 化学式: C₂₇H₄₅NO₂
• 分子量: 415.66
• InChiKey: GRMNIFYZNANARN-LHIOWLTKSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  545.4±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6E)-hydroximinocholest-4-en-3β-ol 在 platinum(IV) oxide 三甲基硅基二氢化磷酸酯 、 氢气 作用下， 以 四氯化碳 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 6-aza-B-homo-5α-cholestan-7-one
  参考文献：
  名称：

  Anastasia, Mario; Allevi, Pietro; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1986, p. 2123 - 2126

  摘要：

  DOI：
• 作为产物：
  描述：

  胆固醇 在 三氟化硼乙醚 、 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 2.83h， 生成 (6E)-hydroximinocholest-4-en-3β-ol
  参考文献：
  名称：

  类固醇肟和内酰胺的新型合成及其作为抗增殖剂的生物学评估。

  摘要：

  从容易获得的胆固醇和孕烯醇酮开始，已经开发了一种新颖的三步法来获得6a-氮杂-B-均甾族内酰胺。另外，已经建立了从薯os皂苷元开始合成维斯佩蒂林的6a-氮杂-B-同型甾族内酰胺类似物的新方法。在这两种合成途径中，关键中间体是从原料以一步或两步顺序获得的羟基亚氨基衍生物。这些方法避免了在过程中使用有害的氧化剂。检查了新的类固醇肟和内酰胺对几种肿瘤细胞系的抗增殖活性。6,23-二羟基亚氨基衍生物表现出最高的活性，GI50值为11-22µM。

  DOI：

  10.1016/j.steroids.2017.03.008

文献信息

• A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges
  作者：Jianguo Cui、Liliang Huang、Lei Fan、Aimin Zhou

  DOI：10.1016/j.steroids.2007.10.007

  日期：2008.3

  Using beta-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, beta-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6a) via oxidation with pyridinium. chlorochromate (PCC). Selective reduction of 6a by NaBH4 in the presence of CoCl2 gives 24-ethylcholest-4-en-3 beta-ol-6-one (7a). The reaction of 7a with hydroxylamine hydrochloride offers the oxime 8a and the oxidation of 8a by Jones reagent gives the target steroid 1. (6E)-Hydroximinocholest-4-en-3-one (2) and (6E)-hydroximino-24-ethylcholest-4,22-dien-3-one (4) were synthesized by a similar method. The cytotoxicity of the synthesized compounds against sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells were investigated. The presence of a cholesterol-type side chain appears to be necessary for the biological activity. (C) 2007 Elsevier Inc. All rights reserved.
• Synthesis of Cytotoxic 6<i>E</i>-Hydroximino-4-ene Steroids:  Structure/Activity Studies
  作者：Noé Deive、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/jm010867n

  日期：2001.8.1

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.
• Novel synthesis of steroidal oximes and lactams and their biological evaluation as antiproliferative agents
  作者：Roxana Martínez-Pascual、Socorro Meza-Reyes、José Luis Vega-Baez、Penélope Merino-Montiel、José M. Padrón、Ángel Mendoza、Sara Montiel-Smith

  DOI：10.1016/j.steroids.2017.03.008

  日期：2017.6

  new procedure for the synthesis of a 6a-aza-B-homo steroidal lactam analog of vespertilin, starting from diosgenin has been established. In both synthetic pathways, the key intermediate is a hydroxyimino derivative obtained in a one- or two-step sequence from the starting materials. These methods avoid the use of hazardous oxidant agents in the process. The new steroidal oximes and lactams were examined

  从容易获得的胆固醇和孕烯醇酮开始，已经开发了一种新颖的三步法来获得6a-氮杂-B-均甾族内酰胺。另外，已经建立了从薯os皂苷元开始合成维斯佩蒂林的6a-氮杂-B-同型甾族内酰胺类似物的新方法。在这两种合成途径中，关键中间体是从原料以一步或两步顺序获得的羟基亚氨基衍生物。这些方法避免了在过程中使用有害的氧化剂。检查了新的类固醇肟和内酰胺对几种肿瘤细胞系的抗增殖活性。6,23-二羟基亚氨基衍生物表现出最高的活性，GI50值为11-22µM。
• Anastasia, Mario; Allevi, Pietro; Ciuffreda, Pierangela, Journal of the Chemical Society. Perkin transactions I, 1986, p. 2123 - 2126
  作者：Anastasia, Mario、Allevi, Pietro、Ciuffreda, Pierangela、Fiecchi, Alberto、Scala, Antonio

  DOI：——

  日期：——