N-(adamantan-1-yl)-6-hydroxyhexanamide | 924660-63-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(adamantan-1-yl)-6-hydroxyhexanamide
• 英文别名: N-(1-adamantyl)-6-hydroxyhexanamide
• CAS: 924660-63-9
• 化学式: C₁₆H₂₇NO₂
• 分子量: 265.396
• InChiKey: CCULQEABSJADGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(adamantan-1-yl)-6-hydroxyhexanamide 在 sodium cyanoborohydride 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 N-(adamantan-1-yl)-6-[(3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)piperidin-1-yl]hexanamide
  参考文献：
  名称：

  基于异黄花碱和2,5-脱水-2,5-亚氨基-D-葡萄糖醇的葡糖脑苷脂酶药理伴侣用于高雪氏病的干预。

  摘要：

  溶酶体葡糖脑苷脂酶（GC）活性不足引起的高雪氏病是最常见的溶酶体贮积病。临床上重要的GC突变酶通常具有降低的比活性和降低的溶酶体浓度，后者是由于折叠和运输受到损害。我们和其他人已证明，药理分子伴侣通过结合至活性位点，稳定内质网（ER）的中性pH环境中GC的天然构象，使其从ER转运到高尔基体并持续到其上，从而协助GC折叠变体。溶酶体。药理分子伴侣解离后，突变的GC折叠在溶酶体中通常是稳定的，这是因为在低pH环境中进化了折叠，并且折叠的底物浓度高，使GC能够将葡萄糖基神经酰胺水解为葡萄糖和神经酰胺。这项研究的假设是，我们可以结合来自不同化学系列的GC药理分子伴侣结构-活性关系，以提供有效的新型分子伴侣，其包含在活性位点结合的碳水化合物样亚结构和在附近口袋中结合的疏水性亚结构。我们将异黄酮和2,5-脱水-2,5-亚氨基-D-葡萄糖醇活性位点结合的亚结构与疏水性烷基金刚烷基酰胺结合在一起，以提供新

  DOI：

  10.1021/jm060677i
• 作为产物：
  描述：

  6-己内酯 、 金刚烷胺 在 三氯化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 N-(adamantan-1-yl)-6-hydroxyhexanamide
  参考文献：
  名称：

  基于异黄花碱和2,5-脱水-2,5-亚氨基-D-葡萄糖醇的葡糖脑苷脂酶药理伴侣用于高雪氏病的干预。

  摘要：

  溶酶体葡糖脑苷脂酶（GC）活性不足引起的高雪氏病是最常见的溶酶体贮积病。临床上重要的GC突变酶通常具有降低的比活性和降低的溶酶体浓度，后者是由于折叠和运输受到损害。我们和其他人已证明，药理分子伴侣通过结合至活性位点，稳定内质网（ER）的中性pH环境中GC的天然构象，使其从ER转运到高尔基体并持续到其上，从而协助GC折叠变体。溶酶体。药理分子伴侣解离后，突变的GC折叠在溶酶体中通常是稳定的，这是因为在低pH环境中进化了折叠，并且折叠的底物浓度高，使GC能够将葡萄糖基神经酰胺水解为葡萄糖和神经酰胺。这项研究的假设是，我们可以结合来自不同化学系列的GC药理分子伴侣结构-活性关系，以提供有效的新型分子伴侣，其包含在活性位点结合的碳水化合物样亚结构和在附近口袋中结合的疏水性亚结构。我们将异黄酮和2,5-脱水-2,5-亚氨基-D-葡萄糖醇活性位点结合的亚结构与疏水性烷基金刚烷基酰胺结合在一起，以提供新

  DOI：

  10.1021/jm060677i

文献信息

• Reversible single-chain selective point folding via cyclodextrin driven host–guest chemistry in water
  作者：Johannes Willenbacher、Bernhard V. K. J. Schmidt、David Schulze-Suenninghausen、Ozcan Altintas、Burkhard Luy、Guillaume Delaittre、Christopher Barner-Kowollik

  DOI：10.1039/c4cc03218g

  日期：——

  In the present communication we introduce a new platform technology for the reversible folding of single polymer chains in aqueous environment on the basis of cyclodextrin (CD) host–guest chemistry and controlled radical polymerization protocols. The single-chain folding of adamantyl-β-CD α-ω-functionalized poly(N,N-dimethylacrylamide) and its reversion at elevated temperatures were monitored by DLS and nuclear Overhauser enhancement spectroscopy (NOESY).

  在这篇通讯中，我们介绍了一种基于环糊精（CD）主客体化学和可控自由基聚合协议，在水环境中实现单聚合物链可逆折叠的新平台技术。通过 DLS 和核欧豪瑟增强光谱（NOESY）监测了金刚烷基δ-CD δ-Ï-官能化聚（N,N-二甲基丙烯酰胺）的单链折叠及其在高温下的逆转。
• UV Light and Temperature Responsive Supramolecular ABA Triblock Copolymers via Reversible Cyclodextrin Complexation
  作者：Bernhard V. K. J. Schmidt、Martin Hetzer、Helmut Ritter、Christopher Barner-Kowollik

  DOI：10.1021/ma302386w

  日期：2013.2.12

  A novel triblock macromolecular architecture based on cyclodextrin (CD) complexation is presented. A CD-functionalized biocompatible poly(N-(2-hydroxypropyI)methacrylamide) (PHPMA) building block (3800 <= M-n <= 10 600 g mol(-1) 1.29 <= D-M <= 1.46) and doubly guest-containing poly(N,N-dimethylacrylamide) (PDMAAm) (6400 <= Mn <= 15 700 g mol(-1) 1.06 <= D-M <= 1.15) and poly(N,N-diethylacrylamide) (PDEAAm) (5400 <= M-n <= 12 100 g mol(-1) 1.11 <= D-M <= 1.33) segments were prepared via reversible addition fragmentation chain transfer (RAFT) polymerization and subsequently utilized for the formation of a well-defined supramolecular ABA triblock copolymer. The block formation was evidenced via dynamic light scattering (DLS), nuclear Overhauser effect spectroscopy (NOESY), and turbidity measurements. Furthermore, the connection of the blocks was proven to be temperature responsive and in the case of azobenzene guests responsive to the irradiation with UV light. The application of these stimuli leads to the disassembly of the triblock copolymer, which was shown to be reversible. In the case of PDEAAm containing triblock copolymers, the temperature-induced aggregation was investigated as well.
• Photochemical Design of Stimuli-Responsive Nanoparticles Prepared by Supramolecular Host–Guest Chemistry
  作者：Astrid F. Hirschbiel、Bernhard V. K. J. Schmidt、Peter Krolla-Sidenstein、James P. Blinco、Christopher Barner-Kowollik

  DOI：10.1021/acs.macromol.5b00923

  日期：2015.7.14

  We introduce the design of a thermoresponsive nanoparticle via sacrificial micelle formation based on supra-molecular host guest chemistry. Reversible addition fragmentation chain transfer (RAFT) polymerization was employed to synthesize well-defined polymer blocks of poly(N,N-dimethyl-acrylamide) (poly(DMAAm)) (M-n,M-SEC = 10 700 g mol(-1), D = 1.3) and poly(N-isopropylacrylamide) (poly(NiPAAm)) (M-n,M-SEC = 39 700 g mol(-1), D = 1.2), carrying supramolecular recognition units at the chain termini. Further, 2-methoxy-6-methylbenzaldehyde moieties (photoenols, PE) were statistically incorporated into the backbone of the poly(NiPAAm) block as photoactive cross-linking units. Host-guest interactions of adamantane (Ada) (at the terminus of the poly(NiPAAm/PE) chain) and beta-cyclodextrin (CD) (attached to the poly(DMAAm chain end) result in a supramolecular diblock copolymer. In aqueous solution, the diblock copolymer undergoes micellization when heated above the lower critical solution temperature (LCST) of the thermoresponsive poly(NiPAAm/PE) chain, forming the core of the micelle. Via the addition of a 4-arm maleimide cross-linker and irradiation with UV light, the micelle is crosslinked in its core via the photoinduced Diels-Alder reaction of maleimide and PE units. The adamantyl cyclodextrin linkage is subsequently cleaved by the destruction of the beta-CD, affording narrowly distributed thermoresponsive nanoparticles with a trigger temperature close to 30 degrees C. Polymer chain analysis was performed via size exclusion chromatography (SEC), nuclear magnetic resonance (NMR) spectroscopy, and dynamic light scattering (DLS). The size and thermoresponsive behavior of the micelles and nanoparticles were investigated via DLS as well as atomic force microscopy (AFM).