3α-tetrahydropyranyloxy-chol-24-ol | 76987-68-3

• 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: 3α-tetrahydropyranyloxy-chol-24-ol
• 英文别名: 3α-tetrahydropyranyloxycholan-24-ol；3α-tetrahydropyranyloxy-5β-cholan-24-ol；3α-(2-tetrahydropyranyloxy)-24-hydroxy-5β-cholane；3a-Tetrahydropyranyloxy-5b-cholan-24-ol；(4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentan-1-ol
• CAS: 76987-68-3
• 化学式: C₂₉H₅₀O₃
• 分子量: 446.714
• InChiKey: DLLPOCZRABOADI-NAJZGSEVSA-N

物化性质

• 沸点：
  539.5±35.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3α-tetrahydropyranyloxy-chol-24-ol 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.0h， 生成 3'-(3α-hydroxycholan-24-oate)-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl
  参考文献：
  名称：

  Syntheses of potential spin probes for biomembranes - tempo and proxyl nitroxides of lithocholic acid

  摘要：

  The synthesis of a steroidal spin label 10 containing a tempo nitroxide group in the side chain of lithocholic acid 1 is reported. This is the first report of a tempo nitroxide in d steroidal side chain. The methodology involved d Wittig condensation between the steroidal phosphonium ylide 7 and tempone 9. The synthesis Of d proxyl nitroxide 16 with the proxyl group in the side chain of 1 is also described. A mild oxidation of 16 to the corresponding 3-keto spin label 17 in high yield is also achieved.

  DOI：

  10.1016/s0040-4020(01)92284-7
• 作为产物：
  描述：

  methyl 3-O-(2-tetrahydropyranyl)-lithocholate 以 四氢呋喃 、 水 、 氩 为溶剂， 生成 3α-tetrahydropyranyloxy-chol-24-ol
  参考文献：
  名称：

  Novel vitamin D.sub.3 derivative and process for preparing the same

  摘要：

  揭示了一种新的维生素D.sub.3衍生物，化学式为##STR1##（其中R.sub.1为氢或羟基），该衍生物表现出类似于维生素D的强生物活性，并且可用作药物；以及生产该衍生物的方法。

  公开号：

  US04284577A1

文献信息

• Synthesis and olfactory activity of unnatural, sulfated 5β-bile acid derivatives in the sea lamprey (Petromyzon marinus)
  作者：Aaron C. Burns、Peter W. Sorensen、Thomas R. Hoye

  DOI：10.1016/j.steroids.2010.11.010

  日期：2011.2

  sites of oxygenation (hydroxylation or ketonization) of the bile acid derived steroid skeleton were evaluated by screening the compounds for olfactory activity using electro-olfactogram recording. 5beta-Petromyzonol sulfate (9a) elicited a considerable olfactory response at sub-nanomolar concentration. In addition, less oxygenated systems (i.e., 9b-9e) elicited olfactory responses, albeit with less potency

  合成了多种非天然胆汁酸衍生物 (9a-9f) 并用于检查海七鳃鳗 (Petromyzon marinus) 嗅觉系统检测这些化合物的特异性。这些化合物是硫酸岩藻醇 (PS, 1) 的类似物，是海七鳃鳗迁移信息素的一种成分。C5 的立体化学构型（即 5alpha 与 5beta）以及胆汁酸衍生的类固醇骨架的氧化程度和位点（羟基化或酮化）通过使用嗅觉图记录筛选嗅觉活性的化合物来评估。5beta-Petromyzonol 硫酸盐 (9a) 在亚纳摩尔浓度下引起相当大的嗅觉反应。此外，含氧量较低的系统（即 9b-9e）会引起嗅觉反应，尽管效力较低。还检查了海七鳃鳗性信息素模拟物 9f（5beta-3-ketopetromyzonol 硫酸盐），发现其产生的嗅觉反应要低得多。用 9a 和 PS (1) 进行的混合研究表明刺激是通过类似的激活模式发生的，这表明在海七鳃鳗嗅觉中识别同种异体构型（即 5a
• Synthesis of (24S)-hydroxy-and (24S)-24,25-epoxycholesterol analogues, potential agonists of nuclear LXR receptors
  作者：V. A. Khripach、V. N. Zhabinskii、A. V. Antonchick、A. P. Antonchick

  DOI：10.1134/s1068162006060124

  日期：2006.12

  A new approach to the synthesis of a series of isomeric 24-hydroxy- and 24,25-epoxysteroids starting from lithocholic acid was proposed. Sharpless asymmetric hydroxylation of intermediate delta24-olefines was used as a reaction determining the stereochemistry of target compounds. The resulting derivatives are potential agonists of nuclear receptors LXRalpha and LXRbeta and are potentially useful in

  提出了一种新的合成方法，该方法从石胆酸开始合成一系列异构的24-羟基-和24,25-环氧类固醇。中间体δ24-烯烃的无尖锐不对称羟基化反应用作确定目标化合物立体化学的反应。所得衍生物是核受体LXRalpha和LXRbeta的潜在激动剂，可能在结构功能研究中有用。
• Lithocholic Acid Derivatives as Potent Vitamin D Receptor Agonists
  作者：Harue Sasaki、Hiroyuki Masuno、Haru Kawasaki、Ayana Yoshihara、Nobutaka Numoto、Nobutoshi Ito、Hiroaki Ishida、Keiko Yamamoto、Naoya Hirata、Yasunari Kanda、Emiko Kawachi、Hiroyuki Kagechika、Aya Tanatani

  DOI：10.1021/acs.jmedchem.0c01420

  日期：2021.1.14

  Lithocholic acid (2) was identified as a second endogenous ligand of vitamin D receptor (VDR), though its activity is very weak. In this study, we designed novel lithocholic acid derivatives based on the crystal structure of VDR–ligand-binding domain (LBD) bound to 2. Among the synthesized compounds, 6 bearing a 2-hydroxy-2-methylprop-1-yl group instead of the 3-hydroxy group at the 3α-position of

  Lithocholic acid (2) was identified as a second endogenous ligand of vitamin D receptor (VDR), though its activity is very weak. In this study, we designed novel lithocholic acid derivatives based on the crystal structure of VDR–ligand-binding domain (LBD) bound to 2. Among the synthesized compounds, 6 bearing a 2-hydroxy-2-methylprop-1-yl group instead of the 3-hydroxy group at the 3α-position of
• Biological evaluation of sulfonate and sulfate analogues of lithocholic acid: A bioisosterism-guided approach towards the discovery of potential sialyltransferase inhibitors for antimetastatic study
  作者：Ser John Lynon P. Perez、Chia-Ling Chen、Tzu-Ting Chang、Wen-Shan Li

  DOI：10.1016/j.bmcl.2024.129760

  日期：2024.6

  occurring bile acid lithocholic acid (LCA) has been a crucial core structure for many non-sugar-containing sialyltranferase (ST) inhibitors documented in literature. With the aim of elucidating the impact of the terminal carboxyl acid substituent of LCA on its ST inhibition, in this present study, we report the (bio)isosteric replacement-based design and synthesis of sulfonate and sulfate analogues of LCA

  天然存在的胆汁酸石胆酸 (LCA) 是文献中记载的许多不含糖的唾液酸转移酶 (ST) 抑制剂的关键核心结构。为了阐明 LCA 末端羧酸取代基对其 ST 抑制的影响，在本研究中，我们报告了基于（生物）等排置换的 LCA 磺酸盐和硫酸盐类似物的设计和合成。在这些化合物中，硫酸盐类似物被发现选择性地抑制β-聚糖唾液酸化至少一个数量级，表明与未修饰的母体胆汁酸相比，效力和选择性都有显着改善。分子对接分析支持合成类似物在酶活性位点的结合更强。治疗还通过抑制癌症转移相关整合素/FAK/桩蛋白途径中涉及的信号蛋白的表达来阻碍MDA-MB-231细胞的体外迁移、粘附和侵袭。总的来说，这些发现不仅提供了一种新颖的结构支架，而且为未来开发更有效、更具选择性的 ST 抑制剂提供了宝贵的见解，这些抑制剂对肿瘤转移具有潜在的治疗作用。
• On The Protection of 3α-Hydroxy Group of A/B<i>cis</i>Steroids
  作者：Sharmila Banerjee Mukhopadhyay、Umesh R. Desai、Girish K. Trivedi

  DOI：10.1080/00397919108019755

  日期：1991.3

  The difficulties encountered in the protection of 3-alpha-hydroxy group of lithocholic acid 1 with three different types of protective groups are described. Only benzyl ether derivative was found to be suitable for synthetic transformations. The methodology for the synthesis of benzyl ethers of A/B cis steroids is reported for the first time.