(2S)-2-氨基-N-丙基丙酰胺 | 62072-60-0

• 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: (2S)-2-氨基-N-丙基丙酰胺
• 英文名称: Propanamide, 2-amino-N-propyl-, (S)-
• 英文别名: (2S)-2-amino-N-propylpropanamide
• CAS: 62072-60-0
• 化学式: C₆H₁₄N₂O
• 分子量: 130.19
• InChiKey: ZTZLBRIYZPKLSX-YFKPBYRVSA-N

物化性质

• 沸点：
  267.9±23.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2S)-2-氨基-N-丙基丙酰胺 在 盐酸 、 TEA 、 N,N'-二环己基碳二亚胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Effect of stereochemistry on the transport of Aca-linked β-turn peptidomimetics across a human intestinal cell line

  摘要：

  Transcellular transport is one of the most important barriers facing the development of new therapeutic agents. However, little is known about the specific effects of structure and particularly stereochemistry on cell permeability. An attractive in vitro model has been developed for the direct assessment of cell transport, using the immortalized human epithelial cell line, Caco-2. The present study assesses the effects of stereochemistry on transport in a commonly used beta-turn model system. Thus, L,L- and L,D-Ala-Ala were cyclized with aminocaproic acid, resulting in macrocycles in which the dipeptides correspond to the i + 1 and i + 2 positions of a beta-turn. The transport of these dipeptides across a Caco-2 cell monolayer was determined, along with corresponding acyclic models (L,L- and L,D-CH3CH2C(0)-Ala-Ala-n-Pr). The transport studies were carried out in the presence and absence of verapamil, a known inhibitor of the apically polarized efflux system present in Caco-2 cells. Both apical-->basolateral and basolateral-->apical transport were measured. Measurements made in the presence of verapamil showed that the cyclic peptides experienced a ca. 4-5-fold difference in intrinsic flux depending on stereochemistry, with the L,D isomer being transported at a higher rate. These differences disappeared in the acyclic cases examined (permeability coefficient ratios of the L,D/L,L isomers were 1.04-1.13). These observations are discussed in terms of the conformations and hydrogen-bonding characteristics of the compounds as determined by NMR spectroscopy. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00115-6
• 作为产物：
  描述：

  tert-butyl (1-oxo-1-(propylamino)propan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-氨基-N-丙基丙酰胺
  参考文献：
  名称：

  发现带有氨基酸片段的有效选择性 PI3Kδ 抑制剂

  摘要：

  PI3Kδ的选择性抑制是治疗血液恶性肿瘤的潜在治疗策略。在此，我们报道了一系列带有氨基酸片段的化合物作为有效的选择性 PI3Kδ 抑制剂。其中，化合物A10表现出亚纳摩尔PI3Kδ效力。在细胞测定中，A10对 SU-DHL-6 细胞具有很强的抗增殖作用，引起细胞周期停滞，并诱导 SU-DHL-6 细胞凋亡。对接研究表明A10与PI3Kδ蛋白紧密结合，呈平面构象。总的来说，化合物A10代表了一种有前途的有效且选择性的 PI3Kδ 抑制剂，带有氨基酸片段，尽管对 PI3Kγ 具有中等选择性，但对 PI3Kα 和 β 具有优异的选择性。这项研究表明，使用氨基酸片段代替吡咯烷环是设计有效 PI3Kδ 抑制剂的新策略。

  DOI：

  10.1016/j.bioorg.2023.106594

文献信息

• Structural insight into the aggregation of <scp>l</scp>-prolyl dipeptides and its effect on organocatalytic performance
  作者：Cristina Berdugo、Beatriu Escuder、Juan F. Miravet

  DOI：10.1039/c4ob02003k

  日期：——

  NMR and organocatalytic studies of four dipeptides derived from l-proline are described.

  NMR和有机催化研究了从L-脯氨酸衍生的四个二肽。
• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。
• Herstellung von Analoga von Polyamin-Spinnentoxinen
  作者：Herbert Benz、Manfred Hesse

  DOI：10.1002/hlca.19940770408

  日期：1994.6.29

  Synthesis of Polyamine Analoga of Spider Toxins

  蜘蛛毒素多胺类似物的合成
• The urea-dipeptides show stronger H-bonding propensity to nucleate β-sheetlike assembly than natural sequence
  作者：Damei Ke、Chuanlang Zhan、Xiao Li、Alexander D.Q. Li、Jiannian Yao

  DOI：10.1016/j.tet.2009.07.048

  日期：2009.9

  In this article, we report the distinct solution behavior of a set of urea-dipeptides to that of natural sequence. The urea-dipeptides adopt beta-folding conformations and form into beta-sheetlike assembly in chloroform. Most surprisedly, the urea-dipeptides tend to form interpeptide H-bonding interactions even at a concentration of as low as 0 1 mM, while the natural sequence shows H-bonding propensity at a concentration of about 7 mM, indicating that the urea-dipeptides Show Much stronger H-bonding propensity to nucleate formation of beta-sheetlike assembly than the natural sequence CD spectra reveal that the investigated urea-dipeptides have two negative CD bands, respectively, around 217 nm and 224 nm, supporting the beta-folding conformations and in turn formation of beta-sheetlike assembly. The beta-sheetlike assembly is also confirmed by the XRD reflections, which give two typical d-spacings of 12 7 and 4 8 angstrom, respectively, corresponding to stacking periodicity of the beta-sheets and the spacing between peptide backbones running orthogonal to the beta-sheet axis. (C) 2009 Elsevier Ltd All rights reserved
• Synthesis of Chiral Tropopodands Having L-Amino Acid Moieties and Ability of Their Metal Complexes as an Asymmetric Catalyst
  作者：Ohki Sato、Yusuke Koshiba、Satoshi Sagara、Katsuyoshi Okada

  DOI：10.3987/com-05-s(t)58

  日期：——

  Optical active tropopodands (10 and 11) having neutral L-amino acids and L-histidine moieties were synthesized. Within their metal complexes, Pd complexes of histidine-tropopodands (11b and 11c) bearing bulky amide moieties showed good ability as an asymmetric catalyst in conjugate addition.