(3R,5S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrobenzoate | 1354420-22-6

• 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: (3R,5S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrobenzoate
• CAS: 1354420-22-6
• 化学式: C₃₆H₅₁NO₅
• 分子量: 577.805
• InChiKey: UQRNBKDEMIXRMC-WUVKQGBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  86.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3R,5S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrobenzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 14.0h， 生成 (22E,24S)-3α-hydroxy-5α-stigmastan-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
• 作为产物：
  描述：

  豆甾醇 在 Jones reagent 、 硫酸 、 potassium hydrogencarbonate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 丙酮 、 甲苯 为溶剂， 反应 34.08h， 生成 (3R,5S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 4-nitrobenzoate
  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