(24R,6E)-24-ethyl-6-hydroxyimino-cholest-4-en-3-one

• 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: (24R,6E)-24-ethyl-6-hydroxyimino-cholest-4-en-3-one
• 英文别名: (24R,6E)-24-ethylcholest-6-hydroxyimino-4-en-3-one；(24R,6E)-24-ethylcholest-6-hydroximino-4-en-3-one；6E-hydroximino-24-ethylcholest-4-en-3-one；(6E,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-6-hydroxyimino-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-one
• 化学式: C₂₉H₄₇NO₂
• 分子量: 441.698
• InChiKey: RBDMVPLHNUYCLZ-ZORUVLOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  植物甾醇 在 吡啶 、 chromium(VI) oxide 、 manganese(IV) oxide 、 氢氧化钾 、 氯化亚砜 、 盐酸羟胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 生成 (24R,6E)-24-ethyl-6-hydroxyimino-cholest-4-en-3-one
  参考文献：
  名称：

  Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one- steroids from the sponges Cinachyrella spp

  摘要：

  Two new 6-hydroximino-4en-3-one steroids: (24R, 6E)-24-ethylcholest-6-hydroximino-4-en-3-one (1) and (6E) cholest-6-hydroximino-4-en-3-one (2), accompanied by the known cholest-4-en-3-one were isolated from a mixture of two morphospecies of the sponge Cinachyrella (C. alloclada and C. apion). Use of spectroscopic methods (NMR and MS) was key to establish their structures which were confirmed by synthesis. Described in this report are the fast hydroximino steroids derived from a natural source. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00163-9

文献信息

• Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (I)
  作者：Jian-Guo Cui、Lei Fan、Li-Liang Huang、Hong-Li Liu、Ai-Min Zhou

  DOI：10.1016/j.steroids.2008.09.003

  日期：2009.1

  hydroximino on ring A and B displayed remarkable distinct cytotoxicities against a diversity of cancer cell types. Presence of an oxime group on ring B and a hydroxy on ring A or B resulted in a higher cytotoxicity than other structural motifs. In addition, a cholesterol-type side chain at position 17 was required for the biological activity. Our findings provide new evidence showing the relationship

  化合物的侧链在其生物学功能中起着重要作用。在我们的研究中，我们发现具有不同侧链和羟基氨基在环 A 和 B 上位置的羟基亚氨基类固醇衍生物对多种癌细胞类型显示出显着不同的细胞毒性。环 B 上的肟基团和环 A 或 B 上的羟基导致比其他结构基序更高的细胞毒性。此外，生物活性需要第 17 位的胆固醇型侧链。我们的研究结果提供了新的证据，表明化学结构与生物功能之间的关系。从研究中获得的信息可能有助于设计新型化疗药物。
• Novel synthesis of (24R,6E)-24-ethylcholest-6-hydroxyimino-4-en-3-one, a steroidal oxime fromCinachyrella spp. sponges
  作者：N. B. Kovganko、Yu. G. Chernov

  DOI：10.1007/bf02236428

  日期：2000.3

  (24R,6E)-24-ethylcholest-6-hydroxyimino-4-en-3-one (1), which was isolated previously from Cinachyrella spp. sponges, is synthesized in five steps from beta -sitosterol in 30% overall yield.

  (24R,6E)-24-乙基胆甾烷-6-羟基亚胺基-4-烯-3-酮 (1)，这种化合物是之前从Cinachyrella海绵中分离出来的，其合成路线是从β-淀粉甾醇出发，经过五步反应，总收率为30%。
• 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.
• ——
  作者：N. V. Kovganko、Yu. G. Chernenko

  DOI：10.1023/a:1012522124688

  日期：——

  beta-Sitosterol 1 and the intermediate 5-hydroxy-6-ketosteroids 2 and 3 were used to synthesize 5beta-hydroxy-6-ketosteroid oximes 4 and 5 Dehydration of 5 from Cinachyrella sponges forms (24R,6E)-24-ethylcholest-6-hydroximono-4-en-3-one 6, a steroidal oxime.