2-(diethylamino)ethyl 4-(3-oxo-3-phenylpropylamino)benzoate | 728014-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(diethylamino)ethyl 4-(3-oxo-3-phenylpropylamino)benzoate
• 英文别名: 2-(Diethylamino)ethyl 4-[(3-oxo-3-phenylpropyl)amino]benzoate
• CAS: 728014-17-3
• 化学式: C₂₂H₂₈N₂O₃
• 分子量: 368.476
• InChiKey: FDIWIFCUMSMFAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(diethylamino)ethyl 4-(3-oxo-3-phenylpropylamino)benzoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以62%的产率得到2-(diethylamino)ethyl 4-[(3-hydroxy-3-phenylpropyl)amino]benzoate
  参考文献：
  名称：

  Singh, Satnam; Singh, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 465 - 467

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-吗啉基)苯丙酮盐酸 、 普鲁卡因 以 乙醇 为溶剂， 反应 5.0h， 生成 2-(diethylamino)ethyl 4-(3-oxo-3-phenylpropylamino)benzoate
  参考文献：
  名称：

  Singh, Satnam; Singh, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 465 - 467

  摘要：

  DOI：

文献信息

• Synthesis of β-amino ketones derived from aminobenzoic acids
  作者：G. A. Gevorgyan、G. Yu. Khachvankyan、A. G. Agababyan、N. Z. Akopyan、G. A. Panosyan、M. G. Malakyan

  DOI：10.1134/s1070363217020311

  日期：2017.2

  Alkylation of aminobenzoic acids and their derivatives with 3-diethylamino-1-arylpropan-1-one hydrochlorides gave the corresponding β-aminopropiophenones some of which were tested for antioxidant activity.

  用3-二乙基氨基-1-芳基丙烷-1-酮盐酸盐将氨基苯甲酸及其衍生物烷基化，得到相应的β-氨基苯乙酮，其中一些已被测试抗氧化活性。
• Inhibition of Leishmania infantum Trypanothione Reductase by New Aminopropanone Derivatives Interacting with the NADPH Binding Site
  作者：Valentina Noemi Madia、Davide Ialongo、Elisa Patacchini、Cécile Exertier、Lorenzo Antonelli、Gianni Colotti、Antonella Messore、Valeria Tudino、Francesco Saccoliti、Luigi Scipione、Andrea Ilari、Roberta Costi、Roberto Di Santo

  DOI：10.3390/molecules28010338

  日期：——

  Background: As a result of the paucity of treatment, Leishmaniasis continues to provoke about 60,000 deaths every year worldwide. New molecules are needed, and drug discovery research is oriented toward targeting proteins crucial for parasite survival. Among them, trypanothione reductase (TR) is of remarkable interest owing to its vital role in Leishmania species protozoan parasite life. Our previously identified compound 1 is a novel chemotype endowed with a unique mode of TR inhibition thanks to its binding to a formerly unknown but druggable site at the entrance of the NADPH binding cavity, absent in human glutathione reductase (hGR). Methods: We designed and synthesized new 3-amino-1-arylpropan-1-one derivatives structurally related to compound 1 and evaluated their potential inhibition activity on TR from Leishmania infantum (LiTR). Cluster docking was performed to assess the binding poses of the compounds. Results: The newly synthesized compounds were screened at a concentration of 100 μM in in vitro assays and all of them proved to be active with residual activity percentages lower than 75%. Conclusions: Compounds 2a and 2b were the most potent inhibitors found, suggesting that an additional aromatic ring might be promising for enzymatic inhibition. Further structure–activity relationships are needed to optimize our compounds activity.

  背景：由于缺乏治疗手段，利什曼病每年仍在全球造成约 60,000 人死亡。我们需要新的分子，药物发现研究的方向是针对对寄生虫生存至关重要的蛋白质。其中，胰硫蛋白还原酶（TR）因其在利什曼原虫生活中的重要作用而备受关注。我们之前发现的化合物 1 是一种新的化学类型，它具有独特的 TR 抑制模式，这要归功于它与 NADPH 结合腔入口处一个以前未知但可药用的位点的结合，而这个位点在人类谷胱甘肽还原酶（hGR）中是不存在的。方法：我们设计并合成了与化合物 1 结构相关的新的 3-氨基-1-芳基丙-1-酮衍生物，并评估了它们对幼年利什曼原虫 TR（LiTR）的潜在抑制活性。对化合物的结合位置进行了簇对接评估。结果：在体外实验中以 100 μM 的浓度对新合成的化合物进行了筛选，结果表明所有化合物都具有活性，残留活性低于 75%。结论化合物 2a 和 2b 是目前发现的最有效的抑制剂，这表明额外的芳香环对酶抑制作用可能很有希望。要优化化合物的活性，还需要进一步研究结构-活性关系。
• Singh Satnam, Singh A., Indian J. Chem. B, 33 (1994) N 5, S 465-467
  作者：Singh Satnam, Singh A.

  DOI：——

  日期：——
• Singh, Satnam; Singh, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 5, p. 465 - 467
  作者：Singh, Satnam、Singh, A.

  DOI：——

  日期：——