3-氨基-N-苯乙基苯甲酰胺 | 81882-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-N-苯乙基苯甲酰胺
• 英文名称: 3-amino-N-(β-phenethyl)benzamide
• 英文别名: 3-amino-N-(2-phenylethyl)benzamide
• CAS: 81882-72-6
• 化学式: C₁₅H₁₆N₂O
• mdl: MFCD08691857
• 分子量: 240.305
• InChiKey: RUCCIRQTLQFVOM-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  469.6±38.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  3-氨基-N-苯乙基苯甲酰胺 在 sodium cyanoborohydride 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.5h， 生成 3-(2,5-Dihydroxy-benzylamino)-N-phenethyl-benzamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g
• 作为产物：
  描述：

  间氨基苯甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 3-氨基-N-苯乙基苯甲酰胺
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization

  摘要：

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.

  DOI：

  10.1021/jm000387g

文献信息

• Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure
  作者：Tomohiro Okawa、Yoshio Aramaki、Mitsuo Yamamoto、Toshitake Kobayashi、Shoji Fukumoto、Yukio Toyoda、Tsutomu Henta、Akito Hata、Shota Ikeda、Manami Kaneko、Isaac D. Hoffman、Bi-Ching Sang、Hua Zou、Tetsuji Kawamoto

  DOI：10.1021/acs.jmedchem.7b00443

  日期：2017.8.24

  for heart failure, highly potent and selective GRK2 inhibitors, exhibit potentiation of β-adrenergic signaling in vitro studies. Hydrazone derivative 5 and 1,2,4-triazole derivative 24a were identified as hit compounds by HTS. New scaffold generation and SAR studies of all parts resulted in a 4-methyl-1,2,4-triazole derivative with an N-benzylcarboxamide moiety with highly potent activity toward GRK2

  用于心力衰竭的一类新型治疗药物，高效和选择性的GRK2抑制剂，在体外研究中表现出增强的β-肾上腺素信号传导能力。HTS将衍生物5和1,2,4-三唑衍生物24a鉴定为命中化合物。新一代的脚手架和所有部分的SAR研究都产生了带有N-苄基羧酰胺部分的4-甲基-1,2,4-三唑衍生物，对GRK2的活性很高，对其他激酶的选择性更高。在亚型选择性方面，这些化合物对GRK1、5、6和7表现出足够的选择性，并且对GRK3具有几乎相同的抑制作用。我们的药物化学努力导致发现了115h（GRK2 IC 50= 18 nM），获得了与人GRK2和GRK2抑制剂的共晶体结构，该抑制剂增强了β-肾上腺素能受体（βAR）介导的cAMP积累，并防止了用异丙肾上腺素处理过的表达β2AR的HEK293细胞中βAR的内在化。因此，115h似乎是心力衰竭治疗的一种新型疗法。
• Mechanochemical Conversion of Aromatic Amines to Aryl Trifluoromethyl Ethers
  作者：Michał Jakubczyk、Satenik Mkrtchyan、Mohanad Shkoor、Suneel Lanka、Šimon Budzák、Miroslav Iliaš、Marek Skoršepa、Viktor O. Iaroshenko

  DOI：10.1021/jacs.2c02611

  日期：2022.6.15

  Increased interest in the trifluoromethoxy group in organic synthesis and medicinal chemistry has induced a demand for new, selective, general, and faster methods applicable to natural products and highly functionalized compounds at a later stage of hit-to-lead campaigns. Applying pyrylium tetrafluoroborate, we have developed a mechanochemical protocol to selectively substitute the aromatic amino group

  在有机合成和药物化学中对三氟甲氧基的兴趣日益增加，这引发了对适用于天然产物和高度功能化化合物的新的、选择性的、通用的和更快的方法的需求，这些方法适用于“命中率”活动的后期阶段。应用 pyrylium tetrafluoroborate，我们开发了一种机械化学方案，以选择性地用 OCF 3官能团取代芳族氨基。我们方法的范围包括 31 个环取代苯胺的例子，包括酰胺和磺胺。以优异的产率获得了预期的 S N Ar 产品。所提出的简洁方法为制药行业开辟了通往新化学空间的途径。
• Design, Synthesis, and Biological Evaluation of a Series of Lavendustin A Analogues That Inhibit EGFR and Syk Tyrosine Kinases, as Well as Tubulin Polymerization
  作者：Fanrong Mu、Stephanie L. Coffing、David J. Riese、Robert L. Geahlen、Pascal Verdier-Pinard、Ernest Hamel、Jill Johnson、Mark Cushman

  DOI：10.1021/jm000387g

  日期：2001.2.1

  A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibition of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several compounds in the series were effective inhibitors of both kinases, it seemed questionable whether their inhibitory effects on these kinases were responsible for the cytotoxic properties observed in a variety of human cancer cell cultures. Accordingly, a COMPARE analysis of the cytotoxicity profile of the most cytotoxic member of the series was performed, and the results indicated that its cytotoxicity profile was similar to that of antitubulin agents. This mechanism of action was supported by demonstrating that most compounds in the series were moderately effective as inhibitors of tubulin polymerization. This suggests that the lavendustin A analogues reported here, as well as some of the previously reported lavendustin A analogues, may be acting as cytotoxic agents by a mechanism involving the inhibition of tubulin polymerization.