N-P-phenylethyl-stearoyl amide | 80396-04-9

• 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-P-phenylethyl-stearoyl amide
• 英文别名: N-β-phenylethyl-stearoyl amide；N-phenethylsteramide；N-phenethyl-stearamide；N-Phenaethyl-stearinamid；N-Phenaethyl-stearamid；N-(2-phenylethyl)octadecanamide
• CAS: 80396-04-9
• 化学式: C₂₆H₄₅NO
• 分子量: 387.649
• InChiKey: JSQYZHUPJQWKBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  28
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  硬脂酸 在 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 N-P-phenylethyl-stearoyl amide
  参考文献：
  名称：

  酰胺类衍生物作为乳腺癌细胞MCF-7的强抑制剂的合成及生物学评价

  摘要：

  合成了一系列的甲酰胺（1-4）及其合成类似物（5-14），并评估了其对乳腺癌细胞MCF-7的体外抑制活性。生物活性分析的结果表明，其中的两种酰胺（化合物1和4）和一种合成的类似物（化合物5）对MCF-7细胞系表现出相当的抑制活性，IC 50值分别为29.6、36.2和27.2 µM。

  DOI：

  10.2174/1570180813888160201100814

文献信息

• Use of fatty acid nitrogen derivatives in fatty acid halide preparation
  申请人：UNICHEMA CHEMIE B.V.

  公开号：EP0434389A2

  公开（公告）日：1991-06-26

  The invention provides a process for preparing fatty acid halide by reacting a fatty acid with a halogenating agent optionally followed by hydrolysis of unreacted halogenating agent and separating the fatty acid halide upper layer from the inorganic lower layer characterized in that a fatty acid nitrogen derivative, preferably a fatty amide has been incorporated in the reaction mixture. Preferably the fatty acid is a saturated or unsaturated C₆ to C₂₄ fatty acid and the halogenating agent a phosphorus halide, especially phosphorus trichloride.

  本发明提供了一种制备脂肪酸卤化物的工艺，其方法是使脂肪酸与卤化剂反应，然后水解未反应的卤化剂，将脂肪酸卤化物上层与无机物下层分离，其特征在于反应混合物中加入了脂肪酸氮衍生物，最好是脂肪酰胺。脂肪酸最好是饱和或不饱和的 C₆ 至 C₂₄ 脂肪酸，卤化剂最好是卤化磷，特别是三氯化磷。
• New endocannabinoid-like compounds and their use
  申请人：RESEARCH & INNOVATION SOC. COOP. A R.L.

  公开号：EP1900365A2

  公开（公告）日：2008-03-19

  The present invention describes compounds deriving from chemical reactions between saturated or monounsaturated acyl derivatives and primary amines or primary alcohols that display specific cannabinoid-like pharmacological activity without exhibiting the central unwanted side effects typical of synthetic cannabinoids or endocannabinoids acting on central cannabinoid (CB1) receptors. These compounds, having this pharmacological activity, may be utilised to prevent or to treat pathological conditions and diseases in mammals, including human subjects, that may undergo a clinical improvement upon their administration.

  本发明描述了由饱和或单不饱和酰基衍生物与伯胺或伯醇之间的化学反应所产生 的化合物，这些化合物显示出类似大麻素的特殊药理活性，而不会表现出合成大麻 素或作用于中枢大麻素（CB1）受体的内源性大麻素所特有的中枢性不良副作用。这些具有这种药理活性的化合物可用于预防或治疗哺乳动物（包括人类）的病理状况和疾病，服用后可改善临床症状。
• Synthesis and Identification of Small Molecules that Potently Induce Apoptosis in Melanoma Cells through G1 Cell Cycle Arrest
  作者：Robin S. Dothager、Karson S. Putt、Brittany J. Allen、Benjamin J. Leslie、Vitaliy Nesterenko、Paul J. Hergenrother

  DOI：10.1021/ja042913p

  日期：2005.6.1

  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.
• USE OF ENDOCANNABINOID-LIKE COMPOUNDS FOR TREATING CNS DEGENERATIVE DISORDERS
  申请人：Research & Innovation S.p.A.

  公开号：EP1592418B1

  公开（公告）日：2017-09-06
• Solid-Supported Chloro[1,3,5]triazine. A Versatile New Synthetic Auxiliary for the Synthesis of Amide Libraries
  作者：Simonetta Masala、Maurizio Taddei

  DOI：10.1021/ol990215h

  日期：1999.11.1

  [GRAPHICS]2,4,6-Trichloro[1,3,5]triazine was loaded on different types of NH2-functional resins to give a new supported reagent. The best results, in term of yields products, were obtained using the chlorotriazine linked to a polystyrene-poly(ethylene glycol) resin. This reagent was employed for the solution-phase synthesis of different amides and dipeptides.