(S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate | 870533-26-9

• 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
• 英文名称: (S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
• 英文别名: 4-methoxyphenylamino-Phe-Boc；tert-butyl N-[(2S)-1-(4-methoxyanilino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 870533-26-9
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: JAQAIUMFYPXYBL-SFHVURJKSA-N

物化性质

• 熔点：
  132-134 °C
• 沸点：
  586.4±50.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S)-2-amino-N-(4-methoxyphenyl)-3-phenylpropanamide
  参考文献：
  名称：

  末端官能化的含硫脲二肽作为抗肿瘤剂的合成和生物学评估†

  摘要：

  合成了一系列基于末端含有硫脲部分的功能化二肽衍生物的抗肿瘤药，并使用一组癌细胞系评估了其抗增殖活性，并确定了其诱导细胞凋亡的作用和机制。这些化合物对不同的癌细胞系表现出显着的选择性，在微摩尔浓度下的IC 50值为。特别地，化合物I-11似乎是最有效的化合物，至少部分地通过诱导细胞凋亡，对NCI-H460细胞系的IC 50 = 4.85±1.44μM。从机理上讲，化合物I-11诱导caspase-12和CHOP活化，从而通过以下途径触发凋亡信号ROS依赖的内质网途径，使细胞周期停滞在S期。因此，我们得出结论，含有被吸电子取代基末端官能化的硫脲部分的二肽衍生物可能是潜在的抗肿瘤药物，需要进一步研究。

  DOI：

  10.1039/c6ra25590f
• 作为产物：
  描述：

  甲氧苯胺 、 Boc-Phe-SH 在 9-mesityl-10-methylacridinium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以84%的产率得到(S)-tert-butyl (1-((4-methoxyphenyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate
  参考文献：
  名称：

  可见光诱导的酰胺键形成。

  摘要：

  在有机光氧化还原催化剂下开发了无金属，无碱和无添加剂的酰胺键形成反应。这种绿色方法显示出优异的功能选择性，而不会影响其他功能基团，例如醇，酚，醚，酯，卤素或杂环。该方法具有广泛的底物范围，与水和空气的良好相容性以及高产率（≤95％）。通过合成重要的药物分子（例如对乙酰氨基酚，褪黑激素，吗氯贝胺和乙酰唑胺）证明了其潜在的实用性。

  DOI：

  10.1021/acs.orglett.9b03905

文献信息

• Urea-containing peptide boronic acids as potent proteasome inhibitors
  作者：Li-Qiang Han、Xia Yuan、Xing-Yu Wu、Ri-Dong Li、Bo Xu、Qing Cheng、Zhen-Ming Liu、Tian-Yan Zhou、Hao-Yun An、Xin Wang、Tie-Ming Cheng、Ze-Mei Ge、Jing-Rong Cui、Run-Tao Li

  DOI：10.1016/j.ejmech.2016.10.023

  日期：2017.1

  A novel class of urea-containing peptide boronic acids as proteasome inhibitors was designed by introducing a urea scaffold to replace an amido bond. Compounds were synthesized and their antitumor activities were evaluated. After two rounds of optimizations, the compound I-14 was found to be a potent proteasome inhibitor. Compared with Bortezomib, I-14 showed higher potency against the chymotrypsin-like

  通过引入尿素支架取代酰胺键，设计了一类新型的含尿素的肽硼酸作为蛋白酶体抑制剂。合成化合物并评估其抗肿瘤活性。经过两轮优化后，发现化合物I-14是有效的蛋白酶体抑制剂。与Bortezomib相比，I-14对人20S蛋白酶体的胰凝乳蛋白酶样活性具有更高的效力（IC 50  <1 pM），对四种不同癌细胞系具有相似的效力（IC 50  <10 nM），并且具有更好的药代动力学特征。此外，I-14在Bel7404小鼠异种移植模型中显着抑制了肿瘤的生长。I-14对蛋白酶体的优异抑制作用 通过对接和分子动力学研究进行了合理化。
• Proline-based dipeptides with two amide units as organocatalyst for the asymmetric aldol reaction of cyclohexanone with aldehydes
  作者：Fubin Chen、Shi Huang、Hui Zhang、Fengying Liu、Yungui Peng

  DOI：10.1016/j.tet.2008.07.051

  日期：2008.9

  A series of proline-based dipeptide organocatalysts with two amide units (1-16) have been developed and evaluated in the direct catalytic asymmetric aldol reactions of aldehydes with cyclohexanone. These catalysts showed good solubility in organic solvents compared with their corresponding carboxyl terminal dipeptides. The robust amide bond formation allowed structural modifications and fine tuning of catalyst properties by varying the stereo and electronic effects of the terminal amide to affect the ability of hydrogen bonding formation between the catalysts and the substrates. The reactions proceeded smoothly in high yields (up to 99%), enantioselectivities (up to 98% ee) and anti-diastereoselectivities (up to 99:1) in the presence of bifunctional organocatalyst 4 under the optimal reaction conditions. (C) 2008 Elsevier Ltd, All rights reserved.
• INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION
  申请人：ViiV HEATHCARE UK (NO.5) LIMITED

  公开号：US20180072997A1

  公开（公告）日：2018-03-15

  Compounds of Formulas I-VI, including pharmaceutically acceptable salts thereof, and compositions and methods for treating human immunodeficiency virus (HIV) infection are set forth. Formula I is exemplified below:
• Pronounced Self‐Induced Diastereomeric Anisochronism in Anisidine Amino Acid Diamides
  作者：Jan-Michael Menke、Oliver Trapp

  DOI：10.1002/chem.202400623

  日期：——

  The emergent properties resulting from selective supramolecular interactions are of significant importance for materials and chemical systems. For the directed use of such properties, a fundamental understanding of the interaction mechanism and the resulting mode of function is necessary for a tailored design. The self‐induced diastereomeric anisochronism effect (SIDA), which occurs in the intermolecular interaction of chiral molecules, generates unique properties such as chiral self‐recognition and nonlinear effects. Here we show that anisidine amino acid diamides lead to extraordinary signal splitting in NMR spectra through supramolecular interaction and homochiral self‐recognition. By systematic experiments we have investigated the underlying SIDA effect, explored its limits and finally successfully utilized it in the determination of enantiomeric ratios by NMR spectroscopy of chiral ‘SIDA‐inactive’ compounds such as thalidomide.
• Synthesis and biological evaluation of terminal functionalized thiourea-containing dipeptides as antitumor agents
  作者：Ri-Zhen Huang、Bin Zhang、Xiao-Chao Huang、Gui-Bin Liang、Jian-Mei Qin、Ying-Ming Pan、Zhi-Xin Liao、Heng-Shan Wang

  DOI：10.1039/c6ra25590f

  日期：——

  A series of antitumor agents based on terminal functionalized dipeptide derivatives containing the thiourea moiety were synthesized and evaluated for antiproliferative activity using a panel of cancer cell lines, and the effects and mechanism of apoptosis induction were determined. These compounds exhibited significant selectivity to different cancer cell lines with IC50 values at micromolar concentrations

  合成了一系列基于末端含有硫脲部分的功能化二肽衍生物的抗肿瘤药，并使用一组癌细胞系评估了其抗增殖活性，并确定了其诱导细胞凋亡的作用和机制。这些化合物对不同的癌细胞系表现出显着的选择性，在微摩尔浓度下的IC 50值为。特别地，化合物I-11似乎是最有效的化合物，至少部分地通过诱导细胞凋亡，对NCI-H460细胞系的IC 50 = 4.85±1.44μM。从机理上讲，化合物I-11诱导caspase-12和CHOP活化，从而通过以下途径触发凋亡信号ROS依赖的内质网途径，使细胞周期停滞在S期。因此，我们得出结论，含有被吸电子取代基末端官能化的硫脲部分的二肽衍生物可能是潜在的抗肿瘤药物，需要进一步研究。