20S-hydroxymethyl-3β-(tetrahydropyran-2'-yl)oxypregn-5-ene | 34026-84-1

• 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: 20S-hydroxymethyl-3β-(tetrahydropyran-2'-yl)oxypregn-5-ene
• 英文别名: 23,24-Bisnorchol-5-ene-3β,22-diol 3β-Tetrahydropyranyl Ether；23,24-dinorchol-5-ene-3β,22-diol 3-(tetrahydropyran-2-yl)ether；3β-tetrahydropyranyloxy-23-bisnorchol-5-en-22-ol；3β-tetrahydroxypyranyloxy-23-bisnorchol-5-en-22-ol；(2S)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-3-(oxan-2-yloxy)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propan-1-ol
• CAS: 34026-84-1
• 化学式: C₂₇H₄₄O₃
• 分子量: 416.645
• InChiKey: BUGXYDVAMJTSFE-GHMQSXNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  20S-hydroxymethyl-3β-(tetrahydropyran-2'-yl)oxypregn-5-ene 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到3β-(tetrahydropyran-2-yloxy)-23,24-dinorchol-5-en-22-al
  参考文献：
  名称：

  四种甾醇腙类似物的合成、体外抗真菌活性和作用机制对二形性真菌巴西球孢子菌的作用

  摘要：

  描述了新型甾醇腙类似物 (9、10、11 和 12) 的设计和合成，然后使用巴西副球孢子作为生物测试剂，评估它们作为真菌生长抑制剂的作用。化合物 9、10、11 和 12 在真菌生长中产生剂量依赖性效应，尤其是 9、11 和 12，它们在纳摩尔浓度 (100 nM) 下具有活性。当 P. brasiliensis 在其致病性酵母样阶段用上述化合物中的每一种单独处理时，其生长速率降低约 50%，所得存活细胞中甾醇组成的分析表明，最终甾醇降低了 50%和麦角甾醇，并伴随羊毛甾醇水平的增加。这些结果表明，这些化合物以取决于腙基团的立体化学位置的方式抑制酶 Δ(24)-甾醇甲基转移酶 (SMT)。相反，化合物 12 诱导了良好的抗增殖活性，与阻断甾醇生物合成途径中的任何步骤无关，这表明了不同的作用模式。测定 H1 的 X 射线晶体结构以获得关于甾醇腙的环和侧链构象的信息。甾醇腙 (9-12) 和氮甾醇

  DOI：

  10.1016/j.steroids.2011.04.012
• 作为产物：
  描述：

  孕烯醇酮 在 sodium hydroxide 、 9-borabicyclononane 、 potassium tert-butylate 、 双氧水 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 35.0h， 生成 20S-hydroxymethyl-3β-(tetrahydropyran-2'-yl)oxypregn-5-ene
  参考文献：
  名称：

  Synthesis of potential pregnenolone and progesterone spin probes for biomembranes and immunoassays

  摘要：

  The synthesis and characterization of four new steroidal spin labels, viz., 3'-[[(pregn-5-en-3 beta-ol-20S-yl)methyl]oate]- 2',2',5',5'-tetramethylpyrrolidine-1'-oxyl,3'-[[(pregn-4-en-3- one-20S-yl)methyl]oate]-2',2',5'.5'-tetra methyl pyrrolidine-1'-oxyl, 3 "[(3 beta-acetoxypregn-5-en-20-one-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2 ",2 ",5 ",5 "-tetramethyl pyrrolidine-1 "-oxyl and 3 "-[(pregn-5-en-3,20-dione-16 alpha-yl)prop-2'xi-ol-3'xi-oate]-2',2',5',5'-tetramethylpyrrolidine-1'-oxyl has been described which involves functionalization of the parent hormone at C-20 and C-16. The key step to all the products was the condensation of 3-carboxyproxyl with the derivatized synthons. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01187-9

文献信息

• Synthesis of cholesterol analogs having varying length alkyl side chains including cholesterol-23, 23, 24, 24, 25, 26, 26, 26, 27, 27, 27-d11 as probes of cholesterol's functions and properties
  作者：Dong Jae Baek、Robert Bittman

  DOI：10.1016/j.chemphyslip.2013.08.003

  日期：2013.10

  long-chain analogs of cholesterol were prepared by alkylation of cyano-containing sterols with isopentyl-d11 4-methylbenzenesulfonate (1.0 equiv.) or with isoalkyl bromides, followed by reductive decyanation with excess potassium metal and a crown ether in toluene. The products are potentially useful probes of the role of the side-chain of cholesterol in the sterol's interactions with membrane lipids and proteins

  胆固醇23、23、24、24、25、26、26、26、27、27、27 -d 11和未氘化的胆固醇长链类似物是通过将含氰基的甾醇与异戊基-d 11 4-烷基化制备的甲基苯磺酸盐（1.0当量）或与异烷基溴化物混合，然后在甲苯中用过量的金属钾和冠醚进行还原性脱氰。该产品是胆固醇侧链在固醇与膜脂质和蛋白质相互作用中的作用的潜在有用探针。
• FREE CHOLESTEROL ANALOGS BEARING A BORON DIPYRROMETHENE DIFLUORO (BODIPY) FLUOROPHORE IN THE SIDE CHAIN AND METHOD OF PREPARATION AND USE THEREOF
  申请人：Bittman Robert

  公开号：US20080177059A1

  公开（公告）日：2008-07-24

  The present invention relates to free cholesterol analogs bearing a boron dipyrromethene difluoro (BODIPY) fluorophore in the side chain and methods of preparation. The compounds of the present invention can be used in fluorescence spectroscopy and fluorescence microscopy to visualize the exchange, distribution, and trafficking of free cholesterol between living cells and to monitor the movement of free cholesterol between ordered and disordered lipid domains in membranes.

  本发明涉及带有硼二吡咯甲烷二氟（BODIPY）荧光团的游离胆固醇类似物及其制备方法。本发明的化合物可用于荧光光谱学和荧光显微镜技术，以可视化活细胞之间游离胆固醇的交换、分布和转运，并监测游离胆固醇在膜中有序和无序脂质域之间的运动。
• Synthesis of Cholesterol Analogues Bearing BODIPY Fluorophores by Suzuki or Liebeskind-Srogl Cross-Coupling and Evaluation of Their Potential for Visualization of Cholesterol Pools
  作者：Zheng Liu、Seth G Thacker、Sara Fernandez-Castillejo、Edward B. Neufeld、Alan T. Remaley、Robert Bittman

  DOI：10.1002/cbic.201402042

  日期：2014.9.22

  All roads lead to BODIPY: Versatile BODIPY–cholesterol conjugates were synthesized in which the key steps were Suzuki or Liebeskind–Srogl cross‐coupling of cholesterol phenyl moieties with structurally diverse BODIPY scaffolds (blue). These conjugates were used to enable the simultaneous tracking of different cellular cholesterol pools by confocal microscopy and flow cytometry.

  条条大路通BODIPY：合成了多功能的BODIPY-胆固醇偶联物，其中关键步骤是胆固醇苯基部分与结构多样的BODIPY支架（蓝色）的Suzuki或Liebeskind-Srogl交叉偶联。这些偶联物用于通过共聚焦显微镜和流式细胞术同时跟踪不同的细胞胆固醇池。
• Stable isotope-labeled vitamin D, metabolites and chemical analogs: synthesis and use in mass spectrometric studies
  作者：Ruth D. Coldwell、D.J.H. Trafford、M.J. Varley、D.N. Kirk、H.L.J. Makin

  DOI：10.1016/0039-128x(90)90010-9

  日期：1990.10

  for the measurement of vitamin D and its metabolites using stable isotope-labeled internal standards and mass spectrometry are reviewed. The synthesis of both labeled and unlabeled standards is illustrated, and details of the synthesis of (26,26,27,27,27(-2)H5)-25,26-dihydroxyvitamin D3 and (28,28,28(-2)H3)-24,25-dihydroxyvitamin D2 are given. The use of in vitro biologic systems for the production of

  综述了使用稳定同位素标记的内标和质谱法测量维生素 D 及其代谢物的方法。说明了标记和未标记标准的合成，以及合成 (26,26,27,27,27(-2)H5)-25,26-dihydroxyvitamin D3 和 (28,28,28(-2) )H3)-24,25-二羟基维生素D2。讨论了使用体外生物系统生产氘化 25-羟基维生素 D3 的进一步代谢物。在分离的灌注大鼠肾脏中使用氘化 25-羟基二氢速甾醇 3 作为底物为确定该系统中形成的 25-羟基二氢速甾醇 3 的许多代谢物的结构提供了有价值的数据。
• Synthesis and Spectral Properties of Cholesterol- and FTY720-Containing Boron Dipyrromethene Dyes
  作者：Zaiguo Li、Robert Bittman

  DOI：10.1021/jo701475q

  日期：2007.10.1

  Two analogues (1, 2) of free cholesterol and one analogue (3) of the immunosuppressive sphingolipid FrY720 containing a boron dipyrromethene chromophore (BODIPY) were synthesized. The synthetic routes involved preparation of boron dipyrromethene moieties (5, 11), bearing a phenylethynyl group at different positions of the chromophore, and lipids (13, 20) bearing an azido group. The dye was tethered to the lipid via a 1,2,3-triazole in the linker by the click reaction. Analogues derived from 11 [in which an (E)-styrylethynyl moiety is bonded to C-5 of BODIPY] exhibited a marked red shift (similar to 70-80 nm) compared with those derived from 5 (in which a phenylethynyl moiety is bonded to C-8 of BODIPY).