(22E,24S)-3β-acetoxy-24-ethyl-5α-cholest-22-en-6-one | 80459-65-0

• 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: (22E,24S)-3β-acetoxy-24-ethyl-5α-cholest-22-en-6-one
• 英文别名: (22E,24S)-3Β-acetoxy-5α-stigmastan-22-en-6-one；(22E,24S)-3β-acetoxy-5α-stigmast-22-en-6-one；(22E)-3β-acetoxy-5α-stigmast-22-en-6-one；3β-acetoxy-5α-stigmast-22t-en-6-one；3β-Acetoxy-5α-stigmast-22t-en-6-on；(22e,24s)-3b-Acetoxy-5a-stigmast-22-en-6-one；[(3S,5S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-6-oxo-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 80459-65-0
• 化学式: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: ONHPTEVGGAKUAY-IPEILNDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (22E,24S)-3β-acetoxy-24-ethyl-5α-cholest-22-en-6-one 在 甲醇 、 palladium 10% on activated carbon 、 水 、 氢气 、 potassium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (24R)-3β-hydroxy-5α-stigmastan-6-one
  参考文献：
  名称：

  Brassinosteroids and analogs as neuroprotectors: Synthesis and structure–activity relationships

  摘要：

  We have demonstrated previously that the brassinosteroid (BR) 24-epibrassinolide exerts neuroprotective effects deriving from its antioxidative properties. In this study, we synthesized 2 natural BRs and 5 synthetic analogs and analyzed their neuroprotective actions in neuronal PC12 cells, against 1-methyl-4-phenylpyridinium (MPP+), a neurotoxin known to induce oxidative stress and degenerescence of dopaminergic neurons characteristic of Parkinsonian brains. We also tested the neuroprotective potential of 2 commercially available BRs. Our results disclosed that 6 of the 9 BRs and analogs tested protected neuronal PC12 cells against MPP+ toxicity. In addition, our structure-activity study suggests that the steroid B-ring and lateral chain play an important role for their neuroprotective action. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.10.009
• 作为产物：
  描述：

  豆甾醇 在 Jones reagent 、 硫酸 、 potassium hydrogencarbonate 、 三乙胺 作用下， 以 水 、 溶剂黄146 、 丙酮 、 甲苯 为溶剂， 反应 9.75h， 生成 (22E,24S)-3β-acetoxy-24-ethyl-5α-cholest-22-en-6-one
  参考文献：
  名称：

  Brassinosteroids and analogs as neuroprotectors: Synthesis and structure–activity relationships

  摘要：

  We have demonstrated previously that the brassinosteroid (BR) 24-epibrassinolide exerts neuroprotective effects deriving from its antioxidative properties. In this study, we synthesized 2 natural BRs and 5 synthetic analogs and analyzed their neuroprotective actions in neuronal PC12 cells, against 1-methyl-4-phenylpyridinium (MPP+), a neurotoxin known to induce oxidative stress and degenerescence of dopaminergic neurons characteristic of Parkinsonian brains. We also tested the neuroprotective potential of 2 commercially available BRs. Our results disclosed that 6 of the 9 BRs and analogs tested protected neuronal PC12 cells against MPP+ toxicity. In addition, our structure-activity study suggests that the steroid B-ring and lateral chain play an important role for their neuroprotective action. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.10.009

文献信息

• Synthesis and crystal structure of [26,27-2H6] 24-epi-cathasterone
  作者：Adelheid Kolbe、Petra Fuchs、Andrea Porzel、Ute Baumeister、Alfred Kolbe、G??nter Adam

  DOI：10.1039/b203323b

  日期：2002.8.23

  The first synthesis of [26,27-2H6]24-epi-cathasterone 8via (20S)-3β-acetoxy-6,6-(ethylenedioxy)-20-formyl-5α-pregnane 5 starting from stigmasterol is described. The aldehyde 5 was alkylated with lithium butyldimethyl-(E)-2,3-dimethyl[3,3,3,4,4,4-2H6]butenylaluminate 6 prepared from 3-[2H3]methyl[4,4,4-2H3]but-1-yne. The structure was determined using spectral data and X-ray crystallographic analysis.

  本论文描述了首次通过(20S)-3β-乙酰氧基-6,6-(亚乙二氧基)-20-甲酰基-5α-孕甾烷 5 从赤霉醇合成 [26,27-2H6]24-epi-cathasterone 8。醛 5 与由 3-[2H3]甲基[4,4,4-2H3]丁-1-炔制备的丁基二甲基-(E)-2,3-二甲基[3,3,3,4,4,4-2H6]丁烯铝酸锂 6 进行烷基化。通过光谱数据和 X 射线晶体分析确定了其结构。
• Mitsui, Nippon Nogeikagaku Kaishi, 1939, vol. 15, p. 795,798, 801
  作者：Mitsui

  DOI：——

  日期：——
• Takatsuto, Suguru; Ikekawa, Nobuo, Journal of the Chemical Society. Perkin transactions I, 1984, # 3, p. 439 - 447
  作者：Takatsuto, Suguru、Ikekawa, Nobuo

  DOI：——

  日期：——
• Wada, Kojiro; Marumo, Shingo, Agricultural and Biological Chemistry, 1981, vol. 45, # 11, p. 2579 - 2586
  作者：Wada, Kojiro、Marumo, Shingo

  DOI：——

  日期：——
• Synthesis and bioactivity evaluation of brassinosteroid analogs
  作者：Javier A Ramı́rez、Osvaldo M Teme Centurión、Eduardo G Gros、Lydia R Galagovsky

  DOI：10.1016/s0039-128x(00)00093-3

  日期：2000.6

  Four new analogs of 28-homocastasterone have been synthesized and completely characterized for the first time from stigmasterol. (22R,23R,24S)-3 beta-acetoxy-22,23-dihydroxy-5 alpha-stigmastan-6-one (17), (22R,23R,24S)-3 beta-bromo-22,23-dihydroxy-5 alpha-stigmastan-6-one (18), (22R,23R,24S)-3 beta-acetoxy-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (20), and (22R,23R,24S)-3 beta-bromo-5,22,23-trihydroxy-5 alpha-stigmastan-6-one (21), were obtained through a synthetic route based on regioselective Delta(5) epoxidation. Compounds 17 and 18, bearing a 5 alpha H moiety, were prepared through a reductive opening of the 5 beta,6 beta epoxy precursor, and compounds 20 and 21, analogs with a 5 alpha OH moiety were obtained by hydrolytic opening of a mixture of 5 alpha,6 alpha and 5 beta,6 beta epoxy precursors. Known compounds 19 and 22 were also obtained following the described synthetic routes, respectively. The new compounds were tested with the traditional auxin-like bioassay for brassinosteroids with 19 and 22 as standards. All compounds were comparatively evaluated for their inhibitory effect on the replication of DNA (HSV-1) virus. (C) 2000 Elsevier Science Inc. All rights reserved.