N-(4-hydroxyphenethyl)stearamide | 21469-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N-(4-hydroxyphenethyl)stearamide
• 英文别名: stearic acid amide；N-Octadecanoyltyramin；N-[2-(4-hydroxyphenyl)ethyl]octadecanamide
• CAS: 21469-25-0
• 化学式: C₂₆H₄₅NO₂
• 分子量: 403.649
• InChiKey: QHHRVLFFENMBCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  577.3±33.0 °C(Predicted)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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-(4-hydroxyphenethyl)stearamide 、 penta(4-formylphenoxy)chloro-cyclo(triphosphazene) 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  具有独特细胞死亡途径的一流CuII和AuIII金属化磷树枝状化合物的有效抗癌功效。

  摘要：

  合成了一流的CuII和AuIII金属化的磷树枝状分子，并显示出对几种侵袭性乳腺癌细胞系的显着抗增殖活性。数据表明，细胞毒性随着烷基链长度的减少而增加，而用AuIII取代CuII则大大增加了金属磷树突的抗增殖活性。非常有趣的是，我们发现细胞死亡途径与由普通树突复合的金属的性质有关。CuII金属化的树突显示出强力的caspase依赖性细胞死亡途径，而AuIII金属化的树突则显示出caspase依赖性的凋亡途径。

  DOI：

  10.1002/chem.202001014
• 作为产物：
  描述：

  硬脂酸 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 N-(4-hydroxyphenethyl)stearamide
  参考文献：
  名称：

  Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest

  摘要：

  Late-stage malignant melanoma is a cancer that is refractory to current chemotherapeutic treatments. The average survival time for patients with such a diagnosis is 6 months. In general, the vast majority of anticancer drugs operate through induction of cell cycle arrest and cell death in either the DNA synthesis (S) or mitosis (M) phase of the cell cycle. Unfortunately, the same mechanisms that melanocytes possess to protect cells from DNA damage often confer resistance to drugs that derive their toxicity from S or M phase arrest. Described herein is the synthesis of a combinatorial library of potential proapoptotic agents and the subsequent identification of a class of small molecules (triphenyl methylamides, TPMAs) that arrest the growth of melanoma cells in the G1 phase of the cell cycle. Several of these TPMAs are quite potent inducers of apoptotic death in melanoma cell lines (IC50 similar to 0.5 mu M), and importantly, some TPMAs are comparatively nontoxic to normal cells isolated from the bone marrow of healthy donors. Furthermore, the TPMAs were found to dramatically reduce the level of active nuclear factor kappa-B (NF kappa B) in the cell; NF kappa B is known to be constitutively active in melanoma, and this activity is critical for the proliferation of melanoma cells and their evasion of apoptosis. Compounds that reduce the level of NF kappa B and arrest cells in the G1 phase of the cell cycle can provide insights into the biology of melanoma and may be effective antimelanoma agents.

  DOI：

  10.1021/ja042913p

文献信息

• 一种两亲性PN=PS型含磷树冠大分子纳米胶 束的制备方法及其药物载体应用
  申请人：东华大学

  公开号：CN111848685B

  公开（公告）日：2021-08-31

  本发明涉及一种两亲性PN＝PS型含磷树冠大分子纳米胶束的制备方法及其药物载体应用，所述将得到的两亲性含磷树冠大分子可在水中自组装为纳米胶束，其内部的疏水空腔能够包埋疏水药物形成稳定的复合物。本发明的方法简单，反应可控性强，易于操作分离，成本低廉，终产物分子量均一，原料来源商品化，具有良好的发展前景。
• 一种含磷树冠大分子基杂化纳米材料及其制 备方法和应用
  申请人：东华大学

  公开号：CN110294777B

  公开（公告）日：2021-11-23

  本发明涉及一种含磷树冠大分子基杂化纳米材料及其制备方法和应用，以六氯环三磷腈为核通过层层修饰的方法合成新型含磷树冠大分子，在其表面修饰吡啶进而得到表面具有金属离子螯合位点的新型含磷树冠大分子，直接络合铜离子和金离子，形成杂化纳米材料，用于制备抗肿瘤药物。本发明原料为商品化来源，制备的含磷树冠大分子的分子量均一，制备方法简单，反应过程可控性高，易于操作，具有多个金属离子螯合位点；本发明制备的杂化纳米材料可用于抗肿瘤研究，拥有良好的应用前景。
• Engineered Stable Bioactive Per Se Amphiphilic Phosphorus Dendron Nanomicelles as a Highly Efficient Drug Delivery System To Take Down Breast Cancer In Vivo
  作者：Liang Chen、Liu Cao、Mengsi Zhan、Jin Li、Dayuan Wang、Régis Laurent、Serge Mignani、Anne-Marie Caminade、Jean-Pierre Majoral、Xiangyang Shi

  DOI：10.1021/acs.biomac.2c00197

  日期：2022.7.11

  Conventional small molecular chemical drugs always have challenging limitations in cancer therapy due to their high systemic toxicity and low therapeutic efficacy. Nanotechnology has been applied in drug delivery, bringing new promising potential to realize effective cancer treatment. In this context, we develop here a new nanomicellar drug delivery platform generated by amphiphilic phosphorus dendrons (1-C17G3.HCl), which could form micelles for effective encapsulation of a hydrophobic anticancer drug doxorubicin (DOX) with a high drug loading content (42.4%) and encapsulation efficiency (96.7%). Owing to the unique dendritic rigid structure and surface hydrophilic groups, large steady void space of micelles can be created for drug encapsulation. The created DOX-loaded micelles with a mean diameter of 26.3 nm have good colloidal stability. Strikingly, we show that the drug-free micelles possess good intrinsic anticancer activity and act collectively with DOX to take down breast cancer cells in vitro and the xenografted tumor model in vivo through upregulation of Bax, PTEN, and p53 proteins for enhanced cell apoptosis. Meanwhile, the resulting 1-C17G3.HCl@DOX micelles significantly abolish the toxicity relevant to the free drug. The findings of this study demonstrate a unique nanomicelle-based drug delivery system created with the self-assembling amphiphilic phosphorus dendrons that may be adapted for chemotherapy of different cancer types.

  传统的小分子化学药物在癌症治疗中总是存在挑战性的局限性，因为它们具有高全身毒性和低治疗效果。纳米技术已应用于药物输送，为有效治疗癌症带来了新的希望。在此背景下，我们开发了一种新的纳米胶束药物输送平台，由两性磷树状分子（1-C17G3.HCl）产生，可形成微胞，有效包裹疏水性抗癌药物阿霉素（DOX），药物负载含量高（42.4%），包裹效率高达96.7%。由于独特的树状刚性结构和表面亲水基团，微胞可形成较大的稳定空隙，用于药物包裹。所形成的平均直径为26.3 nm的载药微胞具有良好的胶体稳定性。值得注意的是，我们发现不含药物的微胞具有良好的内在抗癌活性，并与DOX共同作用，通过上调Bax、PTEN和p53蛋白来增强细胞凋亡，从而在体外和体内异种移植肿瘤模型中杀死乳腺癌细胞。同时，所得的1-C17G3.HCl@DOX微胞显著消除了与游离药物相关的毒性。这项研究的结果表明，利用自组装两性磷树状分子创建了一种独特的基于纳米胶束的药物输送系统，可用于不同癌症类型的化疗。
• Termitomycamides A to E, Fatty Acid Amides Isolated from the Mushroom <i>Termitomyces titanicus</i>, Suppress Endoplasmic Reticulum Stress
  作者：Jae-Hoon Choi、Kohei Maeda、Kaoru Nagai、Etsuko Harada、Mitsuo Kawade、Hirofumi Hirai、Hirokazu Kawagishi

  DOI：10.1021/ol102186p

  日期：2010.11.5

  Five fatty acid amides, termitomycamides A to E (1 to 5), were isolated from the giant edible mushroom Termitomyces titanicus. The structures of 1-5 were determined by the interpretation of spectral data and/or synthesis. Compounds 2 and 5 showed protective activity against endoplasmic reticulum stress-dependent cell death.
• Sciortino; Du Ban, Bollettino Chimico Farmaceutico, 1968, vol. 107, # 8, p. 506 - 511
  作者：Sciortino、Du Ban

  DOI：——

  日期：——