stigmast-4-en-3β-ol-6-one | 130798-13-9

• 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: stigmast-4-en-3β-ol-6-one
• 英文别名: (24r)-3b-Hydroxystigmast-4-en-6-one；(3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• CAS: 130798-13-9
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: JOLKQVLDUDGYNR-ZOJPFNMOSA-N

物化性质

• 熔点：
  140-141 °C
• 沸点：
  537.4±29.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  stigmast-4-en-3β-ol-6-one 在 盐酸羟胺 作用下， 生成 (3S,6E,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-6-hydroxyimino-10,13-dimethyl-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
  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
• 作为产物：
  描述：

  植物甾醇 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 氯化亚砜 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 stigmast-4-en-3β-ol-6-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

• 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.
• SHAMSUZZAMAN;AHMAD, SUHAIL;KHAN, B. Z.;SHAFIULLAH, J. ORG. CHEM., 56,(1991) N, C. 1936-1937
  作者：SHAMSUZZAMAN、AHMAD, SUHAIL、KHAN, B. Z.、SHAFIULLAH

  DOI：——

  日期：——
• Isolation and synthesis of the first natural 6-hydroximino 4-en-3-one- steroids from the sponges Cinachyrella spp
  作者：Jaime Rodríguez、Lucia Nuñez、Solange Peixinho、Carlos Jiménez

  DOI：10.1016/s0040-4039(97)00163-9

  日期：1997.3

  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.