(2S)-2-amino-N-(3,5-dimethylphenyl)-3-phenylpropanamide | 220037-36-5

• 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: (2S)-2-amino-N-(3,5-dimethylphenyl)-3-phenylpropanamide
• CAS: 220037-36-5
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: IOXIJJAGTKCBIR-INIZCTEOSA-N

物化性质

• 沸点：
  465.979±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.136±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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-amino-N-(3,5-dimethylphenyl)-3-phenylpropanamide 在 1-羟基苯并三唑 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  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：

  BOC-L-苯丙氨酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S)-2-amino-N-(3,5-dimethylphenyl)-3-phenylpropanamide
  参考文献：
  名称：

  Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators

  摘要：

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.037

文献信息

• Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3
  作者：Rizhen Huang、Xiaoteng Jing、Xiaochao Huang、Yingming Pan、Yilin Fang、Guibin Liang、Zhixin Liao、Hengshan Wang、Zhenfeng Chen、Ye Zhang

  DOI：10.1021/acs.jmedchem.9b01386

  日期：2020.2.27

  transducer and activator of transcription 3 (STAT3) are important targets in the tumor microenvironment for cancer therapy. In the present study, a set of naphthoquinone aromatic amide-oxime derivatives were designed, which stimulated the immune response via IDO1 inhibition and simultaneously displayed powerful antitumor activity against three selected cancer cell lines through suppressing STAT3 signaling

  Indoleamine-2,3-dioxygenase 1 (IDO1) 和信号转导和转录激活因子 3 (STAT3) 是肿瘤微环境中用于癌症治疗的重要靶点。在本研究中，设计了一组萘醌芳香酰胺肟衍生物，它们通过抑制 IDO1 来刺激免疫反应，同时通过抑制 STAT3 信号传导对三种选定的癌细胞系显示出强大的抗肿瘤活性。代表性化合物8u与IDO1有效结合，相对于商业IDO1抑制剂4-氨基-N-(3-氯-4-氟苯基)-N'-羟基-1,2,5-恶二唑-3-具有更大的抑制活性羧酰亚胺酰胺 (IDO5L) 除了有效抑制 STAT3 的核易位。一贯地，体内试验证明化合物 8u 在野生型 B16-F10 同种移植肿瘤和无胸腺 HepG2 异种移植模型中相对于 1-甲基-1-色氨酸 (1-MT) 和多柔比星 (DOX) 具有更高的抗增殖活性。这种具有双重免疫治疗和抗癌功效的双功能化合物可能代表新一代高效的癌症治疗候选药物。
• Enhanced gelation property due to intra-molecular hydrogen bonding in a new series of bis(amino acid)-functionalized pyridine-2,6-dicarboxamide organogelators
  作者：Hak-Fun Chow、Guo-Xin Wang

  DOI：10.1016/j.tet.2007.02.037

  日期：2007.7

  A series of pyridine-2,6-dicarboxamide derivatives containing two alpha-amino acid pendant groups was prepared and characterized. Three of the synthesized compounds obtained from this series, all having aromatic amino acid side chains, were found to be excellent organo-gelators toward aromatic solvents (mgc similar to 10-20 mg/mL), alcoholic solvents (mgc similar to 4-15 mg/mL), and CCl4 ( mgc similar to 4-10 mg/mL). It was found that the intra-molecular hydrogen bonds between the pyridine dicarboxamide N-Hs and the pyridine N atom were the key structural elements for gel formation. This series of compounds represented one of the rare examples where both inter- and intra-molecular hydrogen bonds were needed for effective gel formation. FTIR, H-1 NMR, and CD spectroscopy revealed that both hydrogen bonding and pi-pi aromatic stacking were the driving forces for gelation. (c) 2007 Elsevier Ltd. All rights reserved.
• 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。