(25R)-spirost-3β,5α-dihydroxy-6-one-3-acetate | 5874-17-9

• 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: (25R)-spirost-3β,5α-dihydroxy-6-one-3-acetate
• 英文别名: (25R)-3β-acetoxy-5α-hydroxyspirostan-6-one；(25R)-3β-acetoxy-5-hydroxy-5α-spirostan-6-one；[(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R,16S,18R)-18-hydroxy-5',7,9,13-tetramethyl-19-oxospiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl] acetate
• CAS: 5874-17-9
• 化学式: C₂₉H₄₄O₆
• 分子量: 488.665
• InChiKey: QQQWWULPCZSUFF-MLIPNZDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (25R)-spirost-3β,5α-dihydroxy-6-one-3-acetate 在 palladium on activated charcoal jones reagent 、 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates

  摘要：

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.050
• 作为产物：
  描述：

  (25R)-5,6-epoxy-spirost-3β-ol-3-acetate 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.17h， 以85%的产率得到(25R)-spirost-3β,5α-dihydroxy-6-one-3-acetate
  参考文献：
  名称：

  通过 A 和 B 环修饰和低价钛 (TiO) 催化的 McMurry 偶联反应合成薯蓣皂苷元衍生物并设计以创造新型生物制剂

  摘要：

  薯蓣皂苷元是一种甾体皂苷元 ((25R)-spirost-5-en-3β-ol)，大量存在于治疗性草药中，例如薯蓣、土茯苓和 Trigonella foenum graecum。它在大量的实验和理论研究中展示了广泛的药理活性和药用特性。它也构成了用于新药开发的一类重要化合物。在目前的研究中，合成和设计了薯蓣皂苷元衍生物，旨在发现新的类固醇生物制剂。在这项工作中，通过低价钛 (TiO) 催化的 McMurry 偶联反应和对薯蓣皂苷元中 A 环和 B 环的结构修饰，合成了新的薯蓣皂苷元衍生物。McMurry 反应通过羰基化合物在低价钛试剂存在下的分子内还原二聚反应以中等收率 (46-47%) 得到 A-nor 和 B-nor 衍生物。薯蓣皂苷元 A 和 B 环上的修饰反应是通过使用高效试剂来完成的，以产生三个不同的系列，产率从中等到高（55-97%）。所有新型衍生物的结构均经 FTIR 确认，1

  DOI：

  10.1016/j.molstruc.2022.132511

文献信息

• In Vitro Neuroprotective and Anti-Inflammatory Activities of Natural and Semi-Synthetic Spirosteroid Analogues
  作者：Laura García-Pupo、Armando Zaldo-Castro、Vassiliki Exarchou、Juan Tacoronte-Morales、Luc Pieters、Wim Vanden Berghe、Yanier Nuñez-Figueredo、René Delgado-Hernández

  DOI：10.3390/molecules21080992

  日期：——

  Two spirosteroid analogues were synthesized and evaluated for their in vitro neuroprotective activities in PC12 cells, against glutamate-induced excitotoxicity and mitochondrial damage in glucose deprivation conditions, as well as their anti-inflammatory potential in LPS/IFNγ-stimulated microglia primary cultures. We also evaluated the in vitro anti-excitotoxic and anti-inflammatory activities of natural and endogenous steroids. Our results show that the plant-derived steroid solasodine decreased PC12 glutamate-induced excitotoxicity, but not the cell death induced by mitochondrial damage and glucose deprivation. Among the two synthetic spirosteroid analogues, only the (25R)-5α-spirostan-3,6-one (S15) protected PC12 against ischemia-related in vitro models and inhibited NO production, as well as the release of IL-1β by stimulated primary microglia. These findings provide further insights into the role of specific modifications of the A and B rings of sapogenins for their neuroprotective potential.

  两种螺旋甾体类似物被合成，并评估了它们在PC12细胞中对谷氨酸诱导的兴奋性毒性和在葡萄糖剥夺条件下对线粒体损伤的体外神经保护活性，以及它们在LPS/IFNγ刺激的初级小胶质细胞培养物中的抗炎潜力。我们还评估了天然和内源性类固醇的体外抗兴奋性毒性和抗炎活性。我们的结果显示，源自植物的类固醇索拉甙降低了PC12细胞中谷氨酸诱导的兴奋性毒性，但并没有降低由线粒体损伤和葡萄糖剥夺引起的细胞死亡。在两种合成的螺旋甾体类似物中，只有(25R)-5α-螺旋甾烷-3,6-酮(S15)保护PC12细胞免受缺血相关体外模型的影响，并抑制了NO的产生，以及刺激的初级小胶质细胞中IL-1β的释放。这些发现为进一步了解皂苷的A环和B环特定修饰对它们的神经保护潜力提供了更多的见解。
• A rapid and simple one-pot procedure for the synthesis of 3β-acetoxy-5α-hydroxy-6-oxo steroids
  作者：Anielka Rosado-Abón、Margarita Romero-Ávila、Martin A. Iglesias-Arteaga

  DOI：10.3998/ark.5550190.0011.a10

  日期：——

  A fast one-pot procedure for the synthesis of 5α-hydroxy-6-oxo steroids is described. Epoxidation of 3β-hydoxy-∆ steroids followed by oxidative cleavage of the resulting epoxide with aqueous CrO3 lead to the desired compounds without affection of labile side chains.

  描述了一种用于合成 5α-羟基-6-氧代类固醇的快速一锅法。3β-羟基-Δ 类固醇的环氧化，然后用 CrO3 水溶液氧化裂解所得环氧化物，生成所需的化合物，而不会影响不稳定的侧链。
• POLYHYDROXYSPIROSTANNONES AS PLANT GROWTH REGULATORS
  申请人：Coll Manchado, Francisco

  公开号：EP1020477A1

  公开（公告）日：2000-07-19

  This present invention is related with the biological chemical branch, and in particular with the preparation of new spirostanics analogues of brassinosteroids and with oxygenated functions in diferent positions of the A ring starting from sapogenins steroidals, through the performance of dihydroxylation reactions to a Δ2-steroid as principal reaction. The preparation of 6-oxo spirobrassinosteroids is described with oxygenated functions in positions 2 and 3 o 3 and 5, with the following general formula (2):    where: Compounds R1 R2 R3 2a CH3COO β CH3COO β H α 2b HO β CH3COO β H α 2c CH3COO β HO β H α 2d HO β HO β H α 2e HO β HO β H β 2f CH3COO β CH3COO β H β 2g CH3COO β CH3COO α H α 2h CH3COO β HO α H α 2i HO β HO α H α 2j HO β HO α H β 2k CH3COO β CH3COO α H β 2l CH3COO α CH3COO β H α 2m HO α HO β H α 2n HO α HO α H α 2ñ CH3COO α CH3COO α H α 2o H CH3COO β HO α 2p H HO β HO α 2q H HO β HO β 2r HO α HO α HO α 2s CH3COO α CH3COO α HO α These synthesized compounds present regulating activity of plant growth in very low concentrations, with wide perspectives for their use in Agriculture.

  本发明与生物化学分支有关，特别是以苷元类甾醇为原料，通过二羟基化反应，以Δ2-类甾醇为主要反应物，制备新的螺烷类黄铜甾醇类似物，并在 A 环的不同位置具有含氧功能。6-oxo 螺甾醇的制备方法如下：通式(2)为在 2、3 或 3、5 位置具有含氧功能的 6-oxo 螺甾醇： 其中 化合物 R1 R2 R3 2a CH3COO β CH3COO β H α 2b HO β CH3COO β H α 2c CH3COO β HO β H α 2d HO β HO β H α 2e HO β HO β H β 2f CH3COO β CH3COO β H β 2g CH3COO β CH3COO α H α 2h CH3COO β HO α H α 2i HO β HO α H α 2j HO β HO α H β 2k CH3COO β CH3COO α H β 2l CH3COO α CH3COO β H α 2m HO α HO β H α 2n HO α HO α H α 2ñ CH3COO α CH3COO α H α 2o H CH3COO β HO α 2p H HO β HO α 2q H HO β HO β 2r HO α HO α HO α 2s CH3COO α CH3COO α HO α 这些合成化合物在极低浓度下就具有调节植物生长的活性，在农业中具有广阔的应用前景。