N-(2-aminoethyl)-2-propylpentanamide | 1211454-43-1

• 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-(2-aminoethyl)-2-propylpentanamide
• CAS: 1211454-43-1
• 化学式: C₁₀H₂₂N₂O
• 分子量: 186.297
• InChiKey: OUTJPBPXJGAYNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Γ-十八碳三烯酸 、 N-(2-aminoethyl)-2-propylpentanamide 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以32%的产率得到(9Z,12Z,15Z)-N-(2-(2-propylpentanamido)ethyl)octadeca-9,12,15-trienamide
  参考文献：
  名称：

  α-Linolenic Acid–Valproic Acid Conjugates: Toward Single-Molecule Polypharmacology for Multiple Sclerosis

  摘要：

  Multiple sclerosis (MS) is a complex inflammatory, degenerative, and demyelinating disease of the central nervous system. Although treatments exist, MS cannot be cured by available drugs, which primarily target neuroinflammation. Thus, it is feasible that a well concerted polypharmacological approach able to act at multiple points within the intricate network of inflammation, neurodegeneration, and demyelination/remyelination pathways would succeed where other drugs have failed. Starting from reported beneficial effects of α-linolenic acid (ALA) and valproic acid (VPA) in MS, and by applying a rational strategy, we developed a small set of codrugs obtained by conjugating VPA and ALA through proper linkers. A cellular profiling identified 1 as a polypharmacological tool able not only to modulate microglia polarization, but also to counteract neurodegeneration and demyelination and induce oligodendrocyte precursor cell differentiation, by acting on multiple biochemical and epigenetic pathways.

  DOI：

  10.1021/acsmedchemlett.0c00375
• 作为产物：
  描述：

  tert-butyl (2-(2-propylpentanamido)ethyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到N-(2-aminoethyl)-2-propylpentanamide
  参考文献：
  名称：

  α-Linolenic Acid–Valproic Acid Conjugates: Toward Single-Molecule Polypharmacology for Multiple Sclerosis

  摘要：

  Multiple sclerosis (MS) is a complex inflammatory, degenerative, and demyelinating disease of the central nervous system. Although treatments exist, MS cannot be cured by available drugs, which primarily target neuroinflammation. Thus, it is feasible that a well concerted polypharmacological approach able to act at multiple points within the intricate network of inflammation, neurodegeneration, and demyelination/remyelination pathways would succeed where other drugs have failed. Starting from reported beneficial effects of α-linolenic acid (ALA) and valproic acid (VPA) in MS, and by applying a rational strategy, we developed a small set of codrugs obtained by conjugating VPA and ALA through proper linkers. A cellular profiling identified 1 as a polypharmacological tool able not only to modulate microglia polarization, but also to counteract neurodegeneration and demyelination and induce oligodendrocyte precursor cell differentiation, by acting on multiple biochemical and epigenetic pathways.

  DOI：

  10.1021/acsmedchemlett.0c00375

文献信息

• Synthesis and biological evaluation of novel AM80 derivatives as antileukemic agents
  作者：Haiyong Bian、Jinhong Feng、Wenfang Xu

  DOI：10.1007/s00044-012-0019-9

  日期：2013.1

  A series of novel AM80 derivatives as antileukemic agents were synthesized and their structures were confirmed by IR, 1H-NMR, and HR-MS spectra. All the target compounds were evaluated for in vitro antiproliferative activities against human leukemic HL-60, NB4, and K562 cell lines. Among these derivatives, compound 4g showed much stronger antiproliferative activities against all the three human leukemic

  合成了一系列新型的AM80衍生物作为抗白血病药物，并通过IR，1 H-NMR和HR-MS光谱证实了其结构。评价所有目标化合物对人白血病HL-60，NB4和K562细胞系的体外抗增殖活性。在这些衍生物中，化合物4g对所有三种人类白血病细胞系的抗增殖活性均强于阳性对照AM80，化合物4b对HL-60和K562细胞的抗增殖活性比AM80高。此外，初步的SAR分析表明AM80与空间位阻小的HDAC抑制剂结合可以产生更有效的抗白血病药物。这些结果将有助于设计更有效的抗白血病药物治疗人类白血病。
• Site‐Specific Deaminative Trifluoromethylation of Aliphatic Primary Amines**
  作者：Jiang‐Hao Xue、Yin Li、Yuan Liu、Qingjiang Li、Honggen Wang

  DOI：10.1002/anie.202319030

  日期：2024.2.19

  A direct deaminative trifluoromethylation of inactivated aliphatic primary amines with N-anomeric amide (Levin's reagent) and bench-stable bpyCu(CF3)3 (Grushin's reagent, bpy=2,2′-bipyridine) under blue light irradiation is reported. The protocol features mild reaction conditions, good functional group tolerance and can be applied to the direct, late-stage trifluoromethylation of natural products and

  据报道，在蓝光照射下，失活的脂肪伯胺与N-异头酰胺（Levin's 试剂）和实验室稳定的 bpyCu(CF 3 ) 3 （Grushin 试剂，bpy=2,2'-联吡啶）直接脱氨三氟甲基化。该方案反应条件温和，官能团耐受性好，可应用于天然产物和生物活性分子的直接后期三氟甲基化。