(24R)-3β,5-dihydroxy-5α-stigmastan-6-one-3-acetate | 55091-77-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (24R)-3β,5-dihydroxy-5α-stigmastan-6-one-3-acetate
• 英文别名: (24R)-3β-acetoxy-5α-hydroxystigmastan-6-one；5-hydroxy-3β-acetoxy-5α-stigmastanone-(6)；5-Hydroxy-3β-acetoxy-5α-stigmastanon-(6)；3β-(acetyloxy)-5-hydroxy-5α-stigmastan-6-one；[(3S,5R,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-5-hydroxy-10,13-dimethyl-6-oxo-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 55091-77-5
• 化学式: C₃₁H₅₂O₄
• 分子量: 488.751
• InChiKey: MLGOEBWFHVXSDQ-LOSFKXSKSA-N

物化性质

• 沸点：
  555.2±40.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (24R)-3β,5-dihydroxy-5α-stigmastan-6-one-3-acetate 在 吡啶 、 氯化亚砜 作用下， 生成 (24R)-3β-acetoxy-24-ethylcholest-4-en-6-one
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  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.

  DOI：

  10.1021/jm010867n
• 作为产物：
  描述：

  β-sitosterol 5,6-epoxide acetate 在 chromium(VI) oxide 作用下， 以 丁酮 为溶剂， 生成 (24R)-3β,5-dihydroxy-5α-stigmastan-6-one-3-acetate
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  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.

  DOI：

  10.1021/jm010867n

文献信息

• 6-(Aminated
  申请人：G. D. Searle & Co.

  公开号：US04001220A1

  公开（公告）日：1977-01-04

  Preparation and the analgesic, antiulcerogenic, hypolipemic, and antimicrobial activity of 6-(aminated methyl)-3.beta.-oxy-5.alpha.-(cholestane/stigmastane)-5,6-diols, salts thereof, and intermediates thereto are disclosed.

  本文披露了6-(氨基甲基)-3.beta.-氧基-5.alpha.-(胆甾烷/固醇烷)-5,6-二醇及其盐和中间体的制备以及其镇痛、抗溃疡、降脂和抗微生物活性。
• Sterols. LXXXVII. Cholesterol and Sitosterol Derivatives
  作者：Russell E. Marker、Ewald Rohrmann

  DOI：10.1021/ja01860a016

  日期：1940.3
• 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.
• Akhrem, A. A.; Kashkan, Yu. N.; Kovganko, N. V., Doklady Chemistry, 1989, vol. 305, # 1-6, p. 92 - 94
  作者：Akhrem, A. A.、Kashkan, Yu. N.、Kovganko, N. V.

  DOI：——

  日期：——
• Synthesis of physanol A and B analogs from β-cytosterol
  作者：N. V. Kovganko、S. K. Ananich

  DOI：10.1007/bf02323289

  日期：1999.9