2a,3a-dihydroxy-24-nor-5a-chol-22-en-6-one | 1562694-08-9

• 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: 2a,3a-dihydroxy-24-nor-5a-chol-22-en-6-one
• 英文别名: (2R,3S,5S,8S,9S,10R,13R,14S,17R)-17-[(2R)-but-3-en-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
• CAS: 1562694-08-9
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: XFPRUZZSDZVOAJ-LYZFPTTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2a,3a-dihydroxy-24-nor-5a-chol-22-en-6-one 在 sodium periodate 、 ruthenium(III) chloride trihydrate 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 (2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-[(2S,3S)-3,4-dihydroxybutan-2-yl]-2,3-dihydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-6-one
  参考文献：
  名称：

  Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor

  摘要：

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.055
• 作为产物：
  描述：

  猪去氧胆酸 在 吡啶 、 盐酸 、 sodium periodate 、 重铬酸吡啶 、 碘苯二乙酸 、 ruthenium(III) chloride trihydrate 、 silica gel 、 copper(II) sulfate 作用下， 以 甲醇 、 四氯乙烯 、 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 2a,3a-dihydroxy-24-nor-5a-chol-22-en-6-one
  参考文献：
  名称：

  Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor

  摘要：

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.055

文献信息

• [EN] CHOLESTANE DERIVATIVES, PREPARATIONS CONTAINING THESE DERIVATIVES AND USE THEREOF<br/>[FR] DÉRIVÉS DE CHOLESTANE, PRÉPARATIONS CONTENANT CES DÉRIVÉS ET LEUR UTILISATION
  申请人：UNIV PALACKEHO

  公开号：WO2022083809A1

  公开（公告）日：2022-04-28

  The invention relates to brassinosteroid-derived cholestane derivatives, their use in the protection of cell damage, injury and cell death and compositions containing these derivatives. New generation of compounds possess also selective antineurodegenerative properties on neuronal cells and tissues and can be particularly used in the treatment and prophylaxis of neurodegenerative disease, particularly in the treatment and prophylaxis of Parkinson's disease.

  本发明涉及铜绿素类甾体衍生物，以及它们在细胞损伤、损伤和细胞死亡保护中的应用和含有这些衍生物的组合物。新一代化合物还具有选择性抗神经退行性疾病的特性，在神经元和组织中可以特别用于神经退行性疾病的治疗和预防，特别是在帕金森病的治疗和预防中。
• Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor
  作者：Ya-Xi Yang、Long-Tai Zheng、Jing-Jing Shi、Bo Gao、Yan-Ke Chen、Hui-Chi Yang、Hong-Li Chen、Yuan-Chao Li、Xue-Chu Zhen

  DOI：10.1016/j.bmcl.2013.12.055

  日期：2014.2

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.