乙基N-丁基甘氨酸酯 | 3182-83-0

• 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: 乙基N-丁基甘氨酸酯
• 英文名称: ethyl 2-(n-butyl)aminoacetate
• 英文别名: ethyl N-butylglycinate；N-butylglycine ethyl ester；Ethyl 2-(butylamino)acetate
• CAS: 3182-83-0
• 化学式: C₈H₁₇NO₂
• mdl: MFCD09953131
• 分子量: 159.228
• InChiKey: OJFGRDHUZSJJPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  7
• 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

反应信息

• 作为反应物：
  描述：

  乙基N-丁基甘氨酸酯 在 N-乙基吗啉 、 碳酸氢钠 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 8.0h， 生成 naphth-2-ylsulfonyl-Asp(OtBu)-N(Bu)Gly-OEt
  参考文献：
  名称：

  Design and Synthesis of Potent and Highly Selective Thrombin Inhibitors

  摘要：

  Thrombin, a serine protease, plays a central role in the initiation and propagation of thrombotic events. An extensive search for new thrombin inhibitors was performed, using an unconventional approach. Screening of small basic molecules for binding in the recognition pocket of thrombin led to the discovery of (aminoiminomethyl)piperidine (amidinopiperidine) as a weak, but intrinsically selective, thrombin inhibitor. Elaboration of this molecule provided compounds which inhibit thrombin with K-i's in the range of 20-50 nM and with selectivities of 1000-4000 against trypsin. These inhibitor compounds show a new and unexpected, binding mode to thrombin. Modification of the central building block and then of one of the hydrophobic substituents led to the discovery of a new family of thrombin inhibitors which has reverted td the former binding mode to thrombin. This last class of compounds shows inhibitory activities in the picomolar range; low toxicity; and a short plasma half life which favors its use for an intravenous application. From this series of thrombin;inhibitors, 19f (Ro 46-6240) was selected for clinical development as an antithrombotic agent for intravenous administration.

  DOI：

  10.1021/jm00049a008
• 作为产物：
  描述：

  正溴丁烷 、 甘氨酸乙酯盐酸盐 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以35%的产率得到乙基N-丁基甘氨酸酯
  参考文献：
  名称：

  [EN] DEFORMYLASE INHIBITOR, PROCESS FOR PREPARING THE SAME, AND ANTIBACTERIAL COMPOSITION COMPRISING THE SAME
  [FR] INHIBITEUR DE DEFORMYLASE, PROCEDE D'ELABORATION, ET COMPOSITION ANTIBACTERIENNE RENFERMANT CET INHIBITEUR

  摘要：

  提供了一种新型化合物，用作脱甲酰酶抑制剂，具有出色的抗菌活性，或其药用盐，以及制备该化合物的方法，以及包含该化合物作为活性成分的抗菌组合物。脱甲酰酶抑制剂有效地对抗广谱细菌，包括对现有抗菌剂产生抗性的细菌。

  公开号：

  WO2004087643A1

文献信息

• Selective Intramolecular CH Amination through the Metalloradical Activation of Azides: Synthesis of 1,3-Diamines under Neutral and Nonoxidative Conditions
  作者：Hongjian Lu、Huiling Jiang、Lukasz Wojtas、X. Peter Zhang

  DOI：10.1002/anie.201005552

  日期：2010.12.27

  N2 is the only by‐product in a stereospecific and highly diastereoselective intramolecular CH amination of sulfamoyl azides with a cobalt(II)‐based metalloradical catalyst (see scheme). The catalytic system has an unusual capacity for the efficient amination of strong primary CH bonds, as well as secondary and tertiary CH bonds, and functional‐group tolerance is excellent owing to the neutral and

  Ñ 2 是唯一的副产物在立体特异性和高度非对映的分子内Ç  H带钴（II）氨磺酰基叠氮化物的胺化的基于metalloradical催化剂（参见方案）。该催化体系具有的强初级C中的高效性胺化一个不寻常的能力 H键，以及仲和叔C  H键，和官能团耐受性是优异的，由于中性和非氧化条件。
• 5-Benzylidene-hydantoins: Synthesis and antiproliferative activity on A549 lung cancer cell line
  作者：Valentina Zuliani、Caterina Carmi、Mirko Rivara、Marco Fantini、Alessio Lodola、Federica Vacondio、Fabrizio Bordi、Pier Vincenzo Plazzi、Andrea Cavazzoni、Maricla Galetti、Roberta R. Alfieri、Pier Giorgio Petronini、Marco Mor

  DOI：10.1016/j.ejmech.2009.01.035

  日期：2009.9

  substituents, was found to be the most active derivative of the series. It inhibited EGFR autophosphorylation and induced DNA damage in A549 cells. Compound 7 and other synthesized 5-benzylidene hydantoin derivatives increased p53 levels, suggesting that the dual mechanism of action was a common feature shared by compound 7 and other member of the series.

  最近有报道称苄基乙内酰脲是一类新的EGFR抑制剂。我们在这里描述一种简单有效的方法，用于并行溶液相合成5-亚苄基乙内酰脲的文库，该文库对人肺腺癌A549细胞系的抗增殖活性进行了评估。检查了乙内酰脲核上1、3和5位的各种取代基。在位置1处有5-亚苄基和亲脂性取代基的情况下，大多数受试化合物均以20μM的浓度抑制细胞增殖。带有1-苯乙基和（E）-5- p的化合物7（UPR1024）发现-OH-亚苄基取代基是该系列中活性最高的衍生物。它抑制EGFR自磷酸化并诱导A549细胞中的DNA损伤。化合物7和其他合成的5-亚苄基乙内酰脲衍生物增加了p53的含量，表明双重作用机制是化合物7和该系列其他成员共有的共同特征。
• Iodine mediated reaction of quinones and N-substituted amino esters to 2-substituted benzo[f]isoindole-4,9-diones
  作者：Yu-jin Li、Huan-ming Huang、Jie Ju、Jian-hong Jia、Liang Han、Qing Ye、Wu-bin Yu、Jian-rong Gao

  DOI：10.1039/c3ra44095h

  日期：——

  A novel and efficient synthesis of benzo[f]isoindole-4,9-diones through the I2-promoted cyclization reaction of N-substituted amino acid esters and quinones has been realized successfully via an unprecedented 1,3-dipolar cycloaddition using KF as the base. Different substituted amino esters were found able to react with quinones through a cycloaddition reaction to afford 2-substituted benzo[f]isoindole-4

  苯并[一种新颖和有效的合成˚F ]通过I异吲哚-4,9-二酮2的促进的环化反应Ñ取代的氨基酸酯和醌已经成功地实现了通过使用KF作为一个前所未有的1,3-偶极环加成基地。发现不同的取代的氨基酯能够通过环加成反应与醌反应，得到2-取代的苯并[ f ]异吲哚-4，9-二酮。这些令人感兴趣的化合物的出人意料的，短暂的，有吸引力的和直接的合成是重要和相关的，并且为合成2-取代的苯并[ f ]异吲哚-4,9-二酮提供了极其优选的方法。
• Synthesis of 2- and 3-substituted-1,2,3,4-tetrahydrodibenzo[<i>f,h</i>]isoquinolines
  作者：Mercedes T. Grande、Gregorio G. Trigo、Mónica M. Söllhuber

  DOI：10.1002/jhet.5570230353

  日期：1986.5

  3,4-tetrahydrodibenzo[f,h]isoquinolines were prepared by a synthetic scheme involving a selective Borch reduction of an amide to the corresponding amine and a Friedel-Crafts cyclization to obtain the dibenzo[f,h]isoquinoline system. The title compounds, which have a similarity to the cell growth inhibitory alkaloid cryptopleurine, failed to exhibit significant protein synthesis inhibitory activity.

  通过合成方案制备一些2-和3-取代的1,2,3,4-四氢二苯并[ f，h ]异喹啉，包括将酰胺选择性博尔希还原为相应的胺，然后进行Friedel-Crafts环化，得到二苯并[ f，h ]异喹啉系统。标题化合物与细胞生长抑制生物碱隐藻碱具有相似性，未能表现出显着的蛋白质合成抑制活性。
• Synthesis, Characterization and Biological Activities of Novel (E)-3-(1-(Alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-dione Derivatives
  作者：Zhao-Yong Zhu、Qing-Ming Shi、Bao-Feng Han、Xian-Feng Wang、Sheng Qiang、Chun-Long Yang

  DOI：10.5012/bkcs.2010.31.9.2467

  日期：2010.9.20

  Twenty novel tetramic acid derivatives (E)-3-(1-(alkyloxyamino)ethylidene)-1-alkylpyrrolidine-2,4-diones were synthesized by the reaction of 3-(1-hydroxyethylidene)pyrrolidine-2,4-diones with O-alkyl hydroxylamines. The title compounds were confirmed by IR, 1 H NMR, MS and elemental analysis. The structure of compound 6rwas further verified by X-ray diffraction crystallography. The bioassays showed

  由 3-(1-羟基亚乙基)吡咯烷-2,4-二酮与O-烷基羟胺。标题化合物通过IR、 1 H NMR、MS和元素分析确认。化合物6r的结构通过X射线衍射晶体学进一步验证。生物测定表明，大多数标题化合物表现出明显的除草和杀真菌活性。