5-(adamantan-1-yl-methoxy)-1-pentanol | 857254-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(adamantan-1-yl-methoxy)-1-pentanol
• 英文别名: adamantanemethoxypentanol；5-(adamant-1-yl-methoxy)-1-pentanol；5-(adamantan-1-ylmethoxy)-pentan-1-ol；5-(1-Adamantylmethoxy)pentan-1-ol
• CAS: 857254-46-7
• 化学式: C₁₆H₂₈O₂
• 分子量: 252.397
• InChiKey: KIHGPSMGDUHOIV-UHFFFAOYSA-N

物化性质

• 沸点：
  326.6±10.0 °C(Predicted)
• 密度：
  1.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(adamantan-1-yl-methoxy)-1-pentanol 在 四溴化碳 、 碘 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.75h， 生成 2,3,4-tri-O-benzyl-6-O-[1-(adamantan-1-yl-methoxy)-pentyl]-1-deoxynojirimycin
  参考文献：
  名称：

  开发金刚烷-1-基-甲氧基官能化的1-脱氧野cin霉素衍生物作为人体葡萄糖神经酰胺代谢的选择性抑制剂。

  摘要：

  在本文中，我们介绍了金刚烷-1-基-甲氧基官能化的1-deoxynojirimycin衍生物的直接合成。所使用的合成路线是灵活的，并且可以用于产生多种亲脂性的单和双官能化的1-脱氧野oji霉素衍生物。此处报道的化合物是基于铅化合物4的亲脂性亚氨基糖，这是一种与糖鞘脂性葡萄糖基神经酰胺代谢有关的三种酶的有效抑制剂。在过去的十年中，基于氨基糖的葡糖神经酰胺合成酶抑制剂（这三种酶之一）受到了越来越多的关注，因为该酶在鞘糖脂生物合成中起着至关重要的作用。结合越来越多的病理过程与过量的鞘糖脂水平相关的事实，葡萄糖基神经酰胺合酶成为非常有吸引力的治疗和研究目标。我们在这里提出的结果证明，将亲脂部分从氮原子重新定位到1-deoxynojirimycin环系统上的其他位置不会导致更有效或更具选择性的葡糖神经酰胺合酶抑制剂。的β氮杂Ç糖苷类似物（17）保留了对葡糖神经酰胺合酶的最佳抑制效力，并且是比治疗剂N

  DOI：

  10.1021/jo061280p
• 作为产物：
  描述：

  1-金刚烷甲醇 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0~75.0 ℃ 、500.0 kPa 条件下， 反应 22.5h， 生成 5-(adamantan-1-yl-methoxy)-1-pentanol
  参考文献：
  名称：

  开发金刚烷-1-基-甲氧基官能化的1-脱氧野cin霉素衍生物作为人体葡萄糖神经酰胺代谢的选择性抑制剂。

  摘要：

  在本文中，我们介绍了金刚烷-1-基-甲氧基官能化的1-deoxynojirimycin衍生物的直接合成。所使用的合成路线是灵活的，并且可以用于产生多种亲脂性的单和双官能化的1-脱氧野oji霉素衍生物。此处报道的化合物是基于铅化合物4的亲脂性亚氨基糖，这是一种与糖鞘脂性葡萄糖基神经酰胺代谢有关的三种酶的有效抑制剂。在过去的十年中，基于氨基糖的葡糖神经酰胺合成酶抑制剂（这三种酶之一）受到了越来越多的关注，因为该酶在鞘糖脂生物合成中起着至关重要的作用。结合越来越多的病理过程与过量的鞘糖脂水平相关的事实，葡萄糖基神经酰胺合酶成为非常有吸引力的治疗和研究目标。我们在这里提出的结果证明，将亲脂部分从氮原子重新定位到1-deoxynojirimycin环系统上的其他位置不会导致更有效或更具选择性的葡糖神经酰胺合酶抑制剂。的β氮杂Ç糖苷类似物（17）保留了对葡糖神经酰胺合酶的最佳抑制效力，并且是比治疗剂N

  DOI：

  10.1021/jo061280p

文献信息

• NON-AMPHIPHILE-BASED WATER-IN-WATER EMULSION AND USES THEREOF
  申请人：LUK Yan-Yeung

  公开号：US20090269323A1

  公开（公告）日：2009-10-29

  The present invention relates to a non-amphiphile-based water-in-water emulsion composition. The non-amphiphile-based water-in-water emulsion composition includes a water-soluble polymer, a non-amphiphilic lyotropic mesogen encapsulated by the water-soluble polymer; and water. In one embodiment, the non-amphiphilic lyotropic mesogen includes, without limitation, a lyotropic chromonic liquid crystal, and more specifically disodium cromoglycate (DSCG). In another embodiment, the water-soluble polymer can include, without limitation, a polyacrylamide, a polyol, a polyvinylpyrrolidone, a polysaccharide, or a water-soluble fluoride-bearing polymer. The present invention also relates to a porous hydrogel made with the use of the non-amphiphile-based water-in-water emulsion. The present invention further relates to using the emulsion and hydrogel for various applications.

  本发明涉及一种非两亲性基材的水包水乳液组合物。该非两亲性基材的水包水乳液组合物包括水溶性聚合物、被水溶性聚合物封装的非两亲性溶致液晶；和水。在一个实施例中，非两亲性溶致液晶包括但不限于溶致色浆液晶，更具体地是无钠 Cromoglicate (DSCG)。在另一个实施例中，水溶性聚合物可以包括但不限于聚丙烯酰胺、聚醇、聚乙烯吡咯烷酮、多糖或水溶性含氟聚合物。本发明还涉及一种用非两亲性基材的水包水乳液制成的多孔水凝胶。本发明进一步涉及使用该乳液和水凝胶用于各种应用。
• [EN] SYNTHESIS OF NOJIRIMYCINS<br/>[FR] SYNTHESE DE NOJIRIMYCINES
  申请人：MACROZYME DNM B V

  公开号：WO2005063706A1

  公开（公告）日：2005-07-14

  Disclosed are methods of preparing substituted nojirimycins represented by the following formula (I) comprising reacting 1-deoxynojirimycin with a reagent prepared by reactingan oxidizing agent with the compound represented by the following formula (II).

  本发明涉及制备以下式（I）所表示的取代诺吉霉素的方法，包括将1-去氧诺吉霉素与通过将氧化剂与以下式（II）所表示的化合物反应制备的试剂反应。
• Exploring the effect of chirality on the therapeutic potential of N-alkyl-deoxyiminosugars: anti-inflammatory response to Pseudomonas aeruginosa infections for application in CF lung disease
  作者：Maria De Fenza、Daniele D'Alonzo、Anna Esposito、Silvia Munari、Nicoletta Loberto、Alessandra Santangelo、Ilaria Lampronti、Anna Tamanini、Alice Rossi、Serena Ranucci、Ida De Fino、Alessandra Bragonzi、Massimo Aureli、Rosaria Bassi、Matteo Tironi、Giuseppe Lippi、Roberto Gambari、Giulio Cabrini、Giovanni Palumbo、Maria Cristina Dechecchi、Annalisa Guaragna

  DOI：10.1016/j.ejmech.2019.04.061

  日期：2019.8

  In the frame of a research program aimed to explore the relationship between chirality of iminosugars and their therapeutic potential, herein we report the synthesis of N-akyl L-deoxyiminosugars and the evaluation of the anti-inflammatory properties of selected candidates for the treatment of Pseudomonas aeruginosa infections in Cystic Fibrosis (CF) lung disease. Target glycomimetics were prepared by the shortest and most convenient approach reported to date, relying on the use of the well-known PS-TPP/I-2 reagent system to prepare reactive alkoxyalkyl iodides, acting as key intermediates. Iminosugars ent-1-3 demonstrated to efficiently reduce the inflammatory response induced by P. aeruginosa in CuFi cells, either alone or in synergistic combination with their D-enantiomers, by selectively inhibiting NLGase. Surprisingly, the evaluation in murine models of lung disease showed that the amount of ent-1 required to reduce the recruitment of neutrophils was 40-fold lower than that of the corresponding D-enantiomer. The remarkably low dosage of the L-iminosugar, combined with its inability to act as inhibitor for most glycosidases, is expected to limit the onset of undesired effects, which are typically associated with the administration of its D-counterpart. Biological results herein obtained place ent-1 and congeners among the earliest examples of L-iminosugars acting as anti-inflammatory agents for therapeutic applications in Cystic Fibrosis. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Process Development of a Potent Glucosylceramide Synthase Inhibitor
  作者：Christopher G.F. Cooper、Edward R. Lee、Richard A. Silva、André J. Bourque、Scott Clark、Sanjeev Katti、Vitaly Nivorozhkin

  DOI：10.1021/op2001222

  日期：2012.5.18

  An economic, scalable process for the production of glucosylceramide synthase (GCS) inhibitor 7 has been developed. Herein we report a three-step synthesis to aldehyde 4 with high yield and purity that employs the selective cleavage of an endocyclic C-O bond of a THP ether using borane/THF as the key step. This particular methodology has not been used previously from a development standpoint and offers an attractive way towards introducing pentanol side chains. Aldehyde 4 is then coupled with deoxynojirimycin via flow hydrogenation using an H-Cube to safely produce the free base of 7, which is isolated as an MSA salt in 50% overall yield. Herein we discuss the evolution of this process from its original form and the thermodynamics of its associated chemistry.
• Adamantane–platinum conjugate hosted in β-cyclodextrin: Enhancing transport and cytotoxicity by noncovalent modification
  作者：Deepali Prashar、Yi Shi、Debjyoti Bandyopadhyay、James C. Dabrowiak、Yan-Yeung Luk

  DOI：10.1016/j.bmcl.2011.10.006

  日期：2011.12

  This work reports the synthesis of a complex of a carboplatin analog having tethered adamantane that is encapsulated in the hydrophobic cavity of beta-cyclodextrin (beta CD) and its cytotoxic activity towards human neuroblastoma cells (SK-N-SH). We found that this inclusion complex of bCD adamantane carboplatin analog exhibited higher cytotoxicity towards SK-N-SH cells than carboplatin itself, and the inclusion complex exhibited a higher binding to plasmid pBR322 deoxyribonucleic acid (DNA) than carboplatin. Confocal fluorescence images of SK-N-SH cells treated with beta CD having an attached fluorescein isothiocyanate (FITC)-tag exhibited fluorescence in the vicinity of the nuclei of the neuroblastoma cells. Direct measurements of the platinum content in SK-N-SH cells using inductively coupled plasma mass spectrometry (ICP-MS) indicated that the uptake rate of carboplatin was about 4 times higher than beta CD adamantane carboplatin analog inclusion complex. When compared to carboplatin, we believe that the higher cytotoxicity of inclusion complex towards SK-N-SH cells is due to its higher DNA binding ability as compared to carboplatin, and more efficient delivery to the nucleus of the cell. This work suggests that the advantage of deliberate noncovalent modification with beta CD through host-guest chemistry may also be broadly applicable to other anticancer agents as well. (C) 2011 Elsevier Ltd. All rights reserved.