N-异丁基甘氨酸乙酯 | 3182-87-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-异丁基甘氨酸乙酯
• 英文名称: ethyl 2-(isobutylamino)acetate
• 英文别名: N-isobutylglycine ethyl ester；ethyl 2-(2-methylpropylamino)acetate
• CAS: 3182-87-4
• 化学式: C₈H₁₇NO₂
• mdl: MFCD11099609
• 分子量: 159.228
• InChiKey: XJBLZCHTARFLLD-UHFFFAOYSA-N

物化性质

• 沸点：
  49-51 °C(Press: 3 Torr)
• 密度：
  0.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.875
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2922499990

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-(异丁基氨基)乙酸	N-Isobutylglycin	3182-85-2	C6H13NO2	131.175

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  2-(异丁基氨基)乙酸	N-Isobutylglycin	3182-85-2	C6H13NO2	131.175

反应信息

• 作为反应物：
  描述：

  N-异丁基甘氨酸乙酯 在 盐酸 、 sodium hydroxide 、 TEA 、 水 作用下， 以 1,4-二氧六环 、 甲醇 、 乙腈 为溶剂， 反应 1.0h， 生成 Fmoc-nleu-oh [Fmoc-n-(异丁基)-甘氨酸]
  参考文献：
  名称：

  Solid-Phase Syntheses of Peptoids using Fmoc-ProtectedN-Substituted Glycines: The Synthesis of (Retro)Peptoids of Leu-Enkephalin and Substance P

  摘要：

  A particularly interesting class of oligomeric peptidomimetics is formed by the peptoids, which consist of N-substituted glycine residues. A solid-phase synthesis method for peptoids is presented in which these residues are introduced using their Fmoc derivatives. This "monomer" method allowed the monitored synthesis of relatively large quantities of pure peptoids as well as the translation of, in principle, any peptide into the corresponding peptoid. The required Fmoc-substituted glycines were accessible by convenient synthesis, and a number of monomers including those containing side chains with functional groups have been synthesized. The use of Fmoc monomers also allowed implementation of a solid-phase synthesis protocol on a commercial peptide synthesizer. The method was exemplified by the solid-phase syntheses of the (retro)peptoids of Leu-enkephalin and substance P. Mass spectrometric studies of (retro)peptoids were essential for their characterization, and the presence of the B- and Y "- type ions allows sequence analysis. Substance P (retro)-peptoids were biologically active. HPLC analysis showed an increased hydrophobicity, and pepsin treatment resulted in greatly reduced degradation compared with the corresponding peptide.

  DOI：

  10.1002/(sici)1521-3765(19980807)4:8<1570::aid-chem1570>3.0.co;2-2
• 作为产物：
  描述：

  异丁胺 、 溴乙酸乙酯 在 三乙胺 作用下， 以98 %的产率得到N-异丁基甘氨酸乙酯
  参考文献：
  名称：

  无添加剂水基介质中更环保的拟肽合成

  摘要：

  为更绿色地合成序列定义的拟肽低聚物开发了高效程序。优化的链伸长过程在水基介质中以独特的N到C方向进行，包括方便的一锅两步脱保护/耦合序列，用于安装每个新的 peptoid 残基。该过程非常高效，每个中间偶联步骤后唯一需要的后处理程序是水萃取。与传统程序形成鲜明对比的是，在合成和后处理过程中，除水外，唯一使用的溶剂是 EtOH、MeOH 或 EtOAc。此外，除了反应介质中的试剂外，不需要专门的水溶性保护基团或添加剂。

  DOI：

  10.1039/d3gc00400g

文献信息

• An Old Story in the Parallel Synthesis World: An Approach to Hydantoin Libraries
  作者：Andrey V. Bogolubsky、Yurii S. Moroz、Olena Savych、Sergey Pipko、Angelika Konovets、Maxim O. Platonov、Oleksandr V. Vasylchenko、Vasyl V. Hurmach、Oleksandr O. Grygorenko

  DOI：10.1021/acscombsci.7b00163

  日期：2018.1.8

  An approach to the parallel synthesis of hydantoin libraries by reaction of in situ generated 2,2,2-trifluoroethylcarbamates and α-amino esters was developed. To demonstrate utility of the method, a library of 1158 hydantoins designed according to the lead-likeness criteria (MW 200–350, cLogP 1–3) was prepared. The success rate of the method was analyzed as a function of physicochemical parameters

  开发了一种通过原位生成的2,2,2-三氟乙基氨基甲酸酯与α-氨基酯反应平行合成乙内酰脲文库的方法。为了证明该方法的实用性，准备了根据铅样标准（MW 200–350，cLogP 1-3）设计的1158个乙内酰脲文库。分析了该方法的成功率与产品理化参数的关系，发现该方法可以被认为是用于铅导向合成的工具。通过合理设计，使用开发的方法进行平行合成，计算机模拟和体外筛选相结合的方法，发现了一种含乙内酰脲的超微摩尔主要分子，可作为Aurora激酶A抑制剂。
• Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents
  申请人：Bayer Corporation

  公开号：US06353006B1

  公开（公告）日：2002-03-05

  This invention relates to 2-arylimino heterocycles, including 2-arylimino-1,3-thiazolidines, 2-arylimino-2,3,4,5-tetrahydro-1,3-thiazines, 2-arylimino-1,3-thiazolidin-4-ones, 2-arylimino-1,3-thiazolidin-5-ones, and 2-arylimino-1,3-oxazolidines, and their use in modulating progesterone receptor mediated processes, and pharmaceutical compositions for use in such therapies.

  这项发明涉及2-芳基亚胺杂环化合物，包括2-芳基亚胺-1,3-噻唑啉、2-芳基亚胺-2,3,4,5-四氢-1,3-噻嗪、2-芳基亚胺-1,3-噻唑啉-4-酮、2-芳基亚胺-1,3-噻唑啉-5-酮和2-芳基亚胺-1,3-噁唑啉，以及它们在调节孕激素受体介导的过程中的应用，以及用于这类治疗的药物组合物。
• [EN] 2,4-SUBSTITUTED PYRIMIDINES AS CYSTEINE PROTEASE INHIBITORS<br/>[FR] PYRIMIDINES 2,4-SUBSTITUEES SERVANT D'INHIBITEURS DE CYSTEINE PROTEASE
  申请人：GLAXO GROUP LTD

  公开号：WO2006027211A1

  公开（公告）日：2006-03-16

  Substituted heteroaryl nitrile derivatives of Formula (I) processes for their preparation, pharmaceutical compositions comprising such compounds and use of the compounds as cysteine protease inhibitors are provided.

  提供了公式（I）的取代杂环亚硝基腈衍生物的制备方法，包括这些化合物的制药组合物以及将这些化合物用作半胱氨酸蛋白酶抑制剂的用途。
• Effect of Double Replacement of L-Pro, D-Pro, D-Leu or Nleu in Hydrophobic Face of Amphipathic α-Helical Model Antimicrobial Peptide on Structure, Cell Selectivity and Mechanism of Action
  作者：Song Yub Shin

  DOI：10.5012/bkcs.2014.35.11.3267

  日期：2014.11.20

  In order to investigate the effects of the double replacement of $\smallL}$-Pro, $\smallD}$-Pro, $\smallD}$-Leu or Nleu (the peptoid residue for Leu) in the hydrophobic face (positions 9 and 13) of amphipathic $\alpha}$-helical non-cell-selective antimicrobial peptide $L_8K_9W_1$ on the structure, cell selectivity and mechanism of action, we synthesized a series of $L_8K_9W_1$ analogs with double replacement of $\smallL}$-Pro, $\smallD}$-Pro, $\smallD}$-Leu or Nleu in the hydrophobic face of $L_8K_9W_1$. In this study, we have confirmed that the double replacement of $\smallL}$-Pro, $\smallD}$-Pro, or Nleu in the hydrophobic face of $L_8K_9W_1$ let to a great increase in the selectivity toward bacterial cells and a complete destruction of $\alpha}$-helical structure. Interestingly, $L_8K_9W_1$-$\smallL}$-Pro, $L_8K_9W_1$-$\smallD}$-Pro and $L_8K_9W_1$-Nleu preferentially interacted with negatively charged phospholipids, but unlike $L_8K_9W_1$ and $L_8K_9W_1$-$\smallD}$-Leu, they did not disrupt the integrity of lipid bilayers and depolarize the bacterial cytoplasmic membrane. These results suggested that the mode of action of $L_8K_9W_1$-$\smallL}$-Pro, $L_8K_9W_1$-$\smallD}$-Pro and $L_8K_9W_1$-Nleu involves the intracellular target other than the bacterial membrane. In particular, $L_8K_9W_1$-$\smallL}$-Pro, $L_8K_9W_1$-$\smallD}$-Pro and $L_8K_9W_1$-Nleu had powerful antimicrobial activity (MIC range, 1 to $4\mu}M$) against methicillin-resistant Staphylococcus aureus (MRSA) and multidrug-resistant Pseudomonas aeruginosa (MDRPA). Taken together, our results suggested that $L_8K_9W_1$-$\smallL}$-Pro, $L_8K_9W_1$-$\smallD}$-Pro and $L_8K_9W_1$-Nleu with great cell selectivity may be promising candidates for novel therapeutic agents, complementing conventional antibiotic therapies to combat pathogenic microorganisms.

  为了研究在亲水性$\alpha}$螺旋非细胞选择性抗菌肽$L_8K_9W_1$的疏水面（位置9和13）上进行的双重替换，即$\smallL}$-Pro、$\smallD}$-Pro、$\smallD}$-Leu或Nleu（Leu的肽类似物残基）对结构、细胞选择性和作用机制的影响，我们合成了一系列在$L_8K_9W_1$的疏水面上进行$\smallL}$-Pro、$\smallD}$-Pro、$\smallD}$-Leu或Nleu双重替换的$L_8K_9W_1$类似物。在本研究中，我们已经证实，在$L_8K_9W_1$的疏水面上进行$\smallL}$-Pro、$\smallD}$-Pro或Nleu的双重替换导致了对细菌细胞的选择性显著增加，并完全破坏了$\alpha}$螺旋结构。有趣的是，$L_8K_9W_1$-$\smallL}$-Pro、$L_8K_9W_1$-$\smallD}$-Pro和$L_8K_9W_1$-Nleu优先与带负电的磷脂相互作用，但与$L_8K_9W_1$和$L_8K_9W_1$-$\smallD}$-Leu不同，它们没有破坏脂质双层的完整性并去极化细菌细胞质膜。这些结果表明，$L_8K_9W_1$-$\smallL}$-Pro、$L_8K_9W_1$-$\smallD}$-Pro和$L_8K_9W_1$-Nleu的作用机制涉及细菌膜以外的细胞内靶点。特别是，$L_8K_9W_1$-$\smallL}$-Pro、$L_8K_9W_1$-$\smallD}$-Pro和$L_8K_9W_1$-Nleu对耐甲氧西林金黄色葡萄球菌（MRSA）和多药耐药铜绿假单胞菌（MDRPA）具有强大的抗菌活性（MIC范围为1至$4\mu}M$）。综上所述，我们的结果表明，具有高细胞选择性的$L_8K_9W_1$-$\smallL}$-Pro、$L_8K_9W_1$-$\smallD}$-Pro和$L_8K_9W_1$-Nleu可能是新疗法的有希望的候选者，补充传统抗生素疗法以对抗病原微生物。
• Fused heterocyclic compounds
  申请人：——

  公开号：US20040082607A1

  公开（公告）日：2004-04-29

  The present invention provides a compound of the formula: wherein ring A is an optionally substituted 5 to 10-membered aromatic ring; R 1 and R 2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group; X is a bond and the like; and L is a divalent hydrocarbon group, and a salt thereof, except 3-(aminomethyl)-2,6,7-trimethyl-4-phenyl-1(2H)-isoquinolinone, 3-(aminomethyl)-2-methyl-4-phenyl-1(2H)-isoquinolinone, 3-(aminomethyl)-6-chloro-2-methyl-4-phenyl-1(2H)-isoquinolinone and 3-(aminomethyl)-2-isopropyl-4-phenyl-1(2H)-isoquinolinone. The compound shows a superior peptidase-inhibitory activity and is useful as an agent for the prophylaxis or treatment of diabetes and the like. 1

  本发明提供了一种化合物，其化学式如下：其中环A是一个可选择取代的5至10成员芳香环；R1和R2相同或不同，每个都是一个可选择取代的碳氢化合物基团或可选择取代的杂环基团；X是一个键等；L是一个二价碳氢基团，以及其盐，但不包括3-(氨甲基)-2,6,7-三甲基-4-苯基-1(2H)-异喹啉酮，3-(氨甲基)-2-甲基-4-苯基-1(2H)-异喹啉酮，3-(氨甲基)-6-氯-2-甲基-4-苯基-1(2H)-异喹啉酮和3-(氨甲基)-2-异丙基-4-苯基-1(2H)-异喹啉酮。该化合物表现出优越的肽酶抑制活性，并可用作糖尿病的预防或治疗剂等。