cholest-5-en-3β-yl 6-hydroxyhexyl ether | 68354-84-7

• 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: cholest-5-en-3β-yl 6-hydroxyhexyl ether
• 英文别名: Cholest-5-en-3beta-yl 6-hydroxyhexyl ether；6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]hexan-1-ol
• CAS: 68354-84-7
• 化学式: C₃₃H₅₈O₂
• 分子量: 486.822
• InChiKey: ZSUPIFBFNIUJOU-IJXDZZBXSA-N

物化性质

• 沸点：
  567.4±43.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  cholest-5-en-3β-yl 6-hydroxyhexyl ether 在 吡啶 、 sodium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 21.0h， 生成 cholest-5-en-3β-yl 6-nitrilohexyl ether
  参考文献：
  名称：

  Functional cholesteryl binding agents: synthesis, characterization, and evaluation of antibody binding to modified phospholipid vesicles

  摘要：

  A series of functionalized cholesteryl derivatives were synthesized. The various lipophilic protein modification agents were analyzed for their protein binding ability. The binding of human IgG, labeled with 125I, to modified phospholipid vesicles was ascertained. Two agents performed well. These were cholest-5-en-3 beta-yl 5-carboxypentyl ether succinimido ester and cholest-5-en-3 beta-yl 6-carboxyhexyl ether succinimido ester.

  DOI：

  10.1021/jm00160a004
• 作为产物：
  描述：

  胆固醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 cholest-5-en-3β-yl 6-hydroxyhexyl ether
  参考文献：
  名称：

  通过调整主链结构和灵活的间隔基长度来自组织胆固醇侧链液晶聚合物

  摘要：

  三种侧链液晶聚合物（SCLCP），其中胆甾醇型液晶元（Chol）与聚丙烯酸酯（PCholAC- m），聚甲基丙烯酸酯（PCholMC- m）和聚（2-乙烯基苯-1,4-二酸酯）连接通过自由基聚合成功地合成了通过不同长度（m = 0、2、4、6、8和10）的亚甲基间隔基形成的（PCholVA- m）主链。使用DSC，POM和SAXS详细研究了聚合物的相行为和结构。结果表明，通过改变主链结构和间隔区长度，Chol-SCLCPs表现出有趣的自组织。所述聚合物最初形成近晶A相，除了没有液晶相的PCholAC-0以外。接下来，聚合物PCholAC-m（m＝ 2、4、6）形成两层近晶A相，其中烷基尾部重叠（SmA 2）。在PCholAC- m（m = 8，10）中观察到两相共存结构，包括双层近晶A相（其中烷基尾部插入到液晶元中）（SmA d）和单层近晶A相，其中液晶元重叠（SmA 1）。对于PCholMC-

  DOI：

  10.1039/c8nj06168h

文献信息

• Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths
  作者：Yuchun Ren、Bin Wang、Xiuqing Zhang

  DOI：10.3762/bjoc.11.122

  日期：——

  A series of azobenzene–cholesterol organogel compounds (M₀–M₁₂) with different spacers were designed and synthesized. The molecular structures were confirmed by ¹H NMR and ¹³C NMR spectroscopy. The rapid and reversible photoresponsive properties of the compounds were investigated by UV–vis spectroscopy. Their thermal phase behaviors were studied by DSC. The length of the spacer plays a crucial role in the gelation. Compound M₆ is the only one that can gelate in ethanol, isopropanol and 1-butanol and the reversible gel–sol transitions are also investigated. To obtain visual insight into the microstructure of the gels, the typical structures of the xerogels were studied by SEM. Morphologies of the aggregates change from flower-like, network and rod with different sizes. By using IR and XRD characterization, it is found that intermolecular H-bonding, the solvents and van der Waals interaction are the main contributions to the specific superstructure.

  一系列具有不同间隔的偶氮苯 - 胆固醇有机凝胶化合物（M0-M12）被设计并合成。分子结构经过1H NMR和13C NMR光谱确认。通过UV-vis光谱研究了化合物的快速可逆光响应特性。它们的热相行为通过DSC进行了研究。间隔物的长度在凝胶化中起着至关重要的作用。化合物M6是唯一能在乙醇、异丙醇和1-丁醇中凝胶化的化合物，其可逆凝胶-溶胶转变也得到了研究。为了获得对凝胶微观结构的视觉洞察，通过SEM研究了干凝胶的典型结构。聚集体的形态从花状、网络状到不同尺寸的棒状发生变化。通过IR和XRD表征，发现分子间氢键、溶剂和范德华相互作用是特定超结构的主要贡献。
• Amphiphilic Diblock Terpolymer PMAgala-<i>b</i>-P(MAA-<i>co</i>-MAChol)s with Attached Galactose and Cholesterol Grafts and Their Intracellular pH-Responsive Doxorubicin Delivery
  作者：Zhao Wang、Ting Luo、Ruilong Sheng、Hui Li、Jingjing Sun、Amin Cao

  DOI：10.1021/acs.biomac.5b01227

  日期：2016.1.11

  In this work, a series of diblock terpolymer poly(6-O-methacryloyl-d-galactopyranose)-b-poly(methacrylic acid-co-6-cholesteryloxy hexyl methacrylate) amphiphiles bearing attached galactose and cholesterol grafts denoted as the PMAgala-b-P(MAA-co-MAChol)s were designed and prepared, and these terpolymer amphiphiles were further exploited as a platform for intracellular doxorubicin (DOX) delivery. First, employing a sequential RAFT strategy with preliminarily synthesized poly(6-O-methacryloyl-1,2:3,4-di-O-isopropylidene-d-galactopyranose) (PMAIpGP) macro-RAFT initiator and a successive trifluoroacetic acid (TFA)-mediated deprotection, a series of amphiphilic diblock terpolymer PMAgala-b-P(MAA-co-MAChol)s were prepared, and were further characterized by NMR, Fourier transform infrared spectrometer (FTIR), gel permeation chromatography (GPC), differential scanning calorimetry (DSC), and a dynamic contact angle testing instrument (DCAT). In aqueous media, spontaneous micellization of the synthesized diblock terpolymer amphiphiles were continuously examined by critical micellization concentration assay, dynamic light scattering (DLS), and transmission electron microscopy (TEM), and the efficacies of DOX loading by these copolymer micelles were investigated along with the complexed nanoparticle stability. Furthermore, in vitro DOX release of the drug-loaded terpolymer micelles were studied at 37 °C in buffer under various pH conditions, and cell toxicities of as-synthesized diblock amphiphiles were examined by MTT assay. Finally, with H1299 cells, intracellular DOX delivery and localization by the block amphiphile vectors were investigated by invert fluorescence microscopy. As a result, it was revealed that the random copolymerization of MAA and MAChol comonomers in the second block limited the formation of cholesterol liquid-crystal phase and enhanced DOX loading efficiency and complex nanoparticle stability, that ionic interactions between the DOX and MAA comonomer could be exploited to trigger efficient DOX release under acidic condition, and that the diblock terpolymer micellular vector could alter the DOX trafficking in cells. Hence, these suggest the pH-sensitive PMAgala-b-P(MAA-co-MAChol)s might be further exploited as a smart nanoplatform toward efficient antitumor drug delivery.

  在本研究中，设计并制备了一系列含有连接半乳糖和胆固醇接枝的二嵌段三元共聚物疏水亲水物，称为 PMAgala-b-P(MAA-co-MAChol)s，并进一步将其作为胞内阿霉素(DOX)递送的平台。首先，采用顺序 RAFT 策略，以预先合成的聚(6-O-甲基丙烯酰基-1,2:3,4-二-O-异丙叉基-d-吡喃半乳糖)(PMAIpGP)大分子 RAFT 引发剂和一系列连续的三氟乙酸(TFA)-介导的脱保护，制备了一系列非离子二嵌段三元共聚物 PMAgala-b-P(MAA-co-MAChol)s，并通过 NMR、傅里叶变换红外光谱仪(FTIR)、凝胶渗透色谱(GPC)、差示扫描量热法(DSC)和动态接触角测试仪(DCAT)进行了进一步表征。在水中，通过临界胶束浓度测定、动态光散射(DLS)和透射电镜(TEM)连续检测合成的二嵌段三元共聚物疏水亲水物的自发性微胶束化，并考察了这些共聚物胶束装载 DOX 的效能和复合纳米颗粒的稳定性。进一步研究了载药三元共聚物胶束在 37 °C 缓冲液中在不同 pH 条件下的体外 DOX 释放，并通过 MTT 试验检测了合成二嵌段疏水亲水物的细胞毒性。最后，通过倒置荧光显微镜对 H1299 细胞进行胞内 DOX 递送和定位研究。结果表明，第二嵌段中 MAA 和 MAChol 共聚单体的无规共聚限制了胆固醇液晶相的形成，提高了 DOX 装载效率和复合纳米颗粒的稳定性，DOX 与 MAA 共聚单体之间的离子相互作用可以利用，在酸性条件下可以触发高效的 DOX 释放，二嵌段三元共聚物胶束载体可以改变 DOX 在细胞中的转运。因此，这些结果表明，pH 敏感的 PMAgala-b-P(MAA-co-MAChol)s 可能进一步作为智能纳米平台用于高效抗癌药物递送。
• Synthesis and characterization of new chiral liquid crystal monomers containing steroid unit
  作者：Qifan Chen、Xiaofeng Liu、Zhihao Guo、Xiaoxu Xu、Yanhua Lu

  DOI：10.1080/15421406.2018.1553744

  日期：2018.7.3

  differential scanning calorimetry, and X-ray diffraction measurements. The experimental results showed that the intermediate compounds containing diosgenyl groups c and d only showed a mesophase and exhibited fan-shaped texture of a smectic A (SA) phase, while the compounds containing terminal cholesteryl groups e and f showed two mesophases and exhibited fan-shaped texture of a SA phase, and oily streak texture

  摘要 为了减少体积位阻，提高薯蓣皂苷元与胆固醇的反应性，获得其衍生物的中间相，对市售的胆固醇和薯蓣皂苷元进行结构修饰。合成了四种新的手性 LC 中间体化合物 (c∼f) 和相应的单体 (M1-M4)，具有不同的更长间隔。本研究中获得的所有介晶化合物的化学结构、光学结构、热行为和中间相结构均通过 FT-IR、1H-NMR、偏光显微镜、差示扫描量热法和 X 射线衍射测量进行表征。实验结果表明，含有二萜基团c和d的中间体化合物仅呈现中间相，呈现近晶A（SA）相的扇形织构，而含有末端胆固醇基团e和f的化合物则表现出两个中间相和SA相的扇形纹理，以及胆甾相的油状条纹纹理和焦锥纹理。四种手性单体 M1-M4 均显示出胆甾醇油状条纹纹理和焦点圆锥纹理。此外，介晶化合物的熔化温度（Tm）和各向同性温度（Ti）随着柔性间隔物长度的增加而降低。与基于胆固醇的中间体化合物或单体相比，基于薯蓣皂苷元的化合物或单体表现出更高的Tm和Ti。四种手性单体
• Self-organizing behaviour of glycosteroidal bolaphiles: insights into lipidic microsegregation
  作者：R. Xu、F. Ali-Rachedi、N. M. Xavier、S. Chambert、F. Ferkous、Y. Queneau、S. J. Cowling、E. J. Davis、J. W. Goodby

  DOI：10.1039/c4ob02191f

  日期：——

  The synthesis of glycosteroidal bolaphile biomimics are described along with the liquid-crystalline behaviours as a function of increasing aliphatic composition.

  描述了糖甾类博拉菲生物模拟物的合成，以及液晶行为随着脂肪族成分增加而变化的情况。
• Steroidal glycolipids as host resistance stimulators
  申请人：Merck & Co., Inc.

  公开号：US04652553A1

  公开（公告）日：1987-03-24

  Described are derivatives of glycolipids with substituted steroids bridged via a medium length hydrocarbon chain to 1-thio-D-mannopyranoses or 1-thio-L-fucopyranoses. These compounds protect an immunocompromised human or animal host against opportunistic infection by virtue of their immunostimulant properties.

  描述了通过中等长度的碳氢链连接到1-硫代-D-甘霖糖或1-硫代-L-岩藻糖的替代类固醇的糖脂衍生物。这些化合物通过其免疫刺激性能保护免疫受损的人类或动物宿主免受机会性感染的侵害。