2-benzyloxycarbonylamino-6-lauroylaminohexanoic acid | 19213-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzyloxycarbonylamino-6-lauroylaminohexanoic acid
• 英文别名: Nε-lauroyl-Nα-carbobenzoxylysine；(2S)-6-(dodecanoylamino)-2-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 19213-80-0
• 化学式: C₂₆H₄₂N₂O₅
• 分子量: 462.63
• InChiKey: SEASHXOZRZWNRY-QHCPKHFHSA-N

物化性质

• 沸点：
  678.1±55.0 °C(Predicted)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  33
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-benzyloxycarbonylamino-6-lauroylaminohexanoic acid 在 三乙烯二胺 、 盐酸 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 Nα,Nω-bis(Nα-lauroyl-Nε-trimethyl-lysine chloride) α,ω-hexylendiamide
  参考文献：
  名称：

  Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities

  摘要：

  Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.

  DOI：

  10.1021/jm101315k
• 作为产物：
  描述：

  月桂酸 在 氯化亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-benzyloxycarbonylamino-6-lauroylaminohexanoic acid
  参考文献：
  名称：

  曼氏血吸虫（SmSirt2）赖氨酸脱酰基酶Sirtuin 2的底物和抑制剂的结构反应性关系。

  摘要：

  目前可用于治疗被忽视的血吸虫病的唯一药物是吡喹酮，耐药性的出现使得对新型治疗剂的研究变得必要和紧迫。为此，靶向曼氏血吸虫表观遗传酶（其调节寄生虫的生命周期）作为一种有前途的方法应运而生。由于人类sirtuin抑制剂对寄生虫存活和繁殖的强烈影响，血吸虫sirtuins被认为是潜在的治疗靶标。曼氏沙门氏菌sirtuin 2（Sm Sirt2）的合成底物的体外测试和肉豆蔻酰化肽的动力学实验证明赖氨酸长链脱酰作用是固有的SmSirt2活性除其首次已知的脱乙酰基酶活性外。对GSK Kinetobox文库进行集中的体外筛选以及已确定的基因敲击物的构效关系，导致了首批具有低微摩尔范围活性的Sm Sirt2抑制剂。几种Sm Sirt2抑制剂在培养中显示出对幼虫血吸虫（存活力）和成虫（配对，产卵）的效力，而对人癌细胞没有一般毒性。

  DOI：

  10.1021/acs.jmedchem.9b00638

文献信息

• Structure–Reactivity Relationships on Substrates and Inhibitors of the Lysine Deacylase Sirtuin 2 from <i>Schistosoma mansoni</i> (<i>Sm</i>Sirt2)
  作者：Daria Monaldi、Dante Rotili、Julien Lancelot、Martin Marek、Nathalie Wössner、Alessia Lucidi、Daniela Tomaselli、Elizabeth Ramos-Morales、Christophe Romier、Raymond J. Pierce、Antonello Mai、Manfred Jung

  DOI：10.1021/acs.jmedchem.9b00638

  日期：2019.10.10

  vitro screening of the GSK Kinetobox library and structure–activity relationships of identified hits led to the first SmSirt2 inhibitors with activity in the low micromolar range. Several SmSirt2 inhibitors showed potency against both larval schistosomes (viability) and adult worms (pairing, egg laying) in culture without general toxicity to human cancer cells.

  目前可用于治疗被忽视的血吸虫病的唯一药物是吡喹酮，耐药性的出现使得对新型治疗剂的研究变得必要和紧迫。为此，靶向曼氏血吸虫表观遗传酶（其调节寄生虫的生命周期）作为一种有前途的方法应运而生。由于人类sirtuin抑制剂对寄生虫存活和繁殖的强烈影响，血吸虫sirtuins被认为是潜在的治疗靶标。曼氏沙门氏菌sirtuin 2（Sm Sirt2）的合成底物的体外测试和肉豆蔻酰化肽的动力学实验证明赖氨酸长链脱酰作用是固有的SmSirt2活性除其首次已知的脱乙酰基酶活性外。对GSK Kinetobox文库进行集中的体外筛选以及已确定的基因敲击物的构效关系，导致了首批具有低微摩尔范围活性的Sm Sirt2抑制剂。几种Sm Sirt2抑制剂在培养中显示出对幼虫血吸虫（存活力）和成虫（配对，产卵）的效力，而对人癌细胞没有一般毒性。
• Cationic Surfactants Derived from Lysine: Effects of Their Structure and Charge Type on Antimicrobial and Hemolytic Activities
  作者：A. Colomer、A. Pinazo、M. A. Manresa、M. P. Vinardell、M. Mitjans、M. R. Infante、L. Pérez

  DOI：10.1021/jm101315k

  日期：2011.2.24

  Three different sets of cationic surfactants from lysine have been synthesized. The first group consists of three monocatenary surfactants with one lysine as the cationic polar head with one cationic charge. The second consists of three monocatenary surfactants with two amino acids as cationic polar head with two positive charges. Finally, four gemini surfactants were synthesized in which the spacer chain and the number and type of cationic charges have been regulated. The micellization process, antimicrobial activity, and hemolytic activity were evaluated. The critical micelle concentration was dependent only on the hydrophobic character of the molecules. Nevertheless, the antimicrobial and hemolytic activities were related to the structure of the compounds as well as the type of cationic charges. The most active surfactants against the bacteria were those with a cationic charge on the trimethylated amino group, whereas all of these surfactants showed low hemolytic character.