N,N'-dibenzoyl-1,3-diaminopropan-2-ol | 101798-10-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-dibenzoyl-1,3-diaminopropan-2-ol
• 英文别名: N,N'-(2-hydroxypropane-1,3-diyl)dibenzamide；N-(3-benzamido-2-hydroxypropyl)benzamide
• CAS: 101798-10-1
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: IUWCPTIFCCEKIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-dibenzoyl-1,3-diaminopropan-2-ol 在 rhodium(III) chloride 、 tritium oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以57%的产率得到tritiated N,N'-dibenzoyl-1,3-diaminopropan-2-ol
  参考文献：
  名称：

  Synthesis and Distribution of Tritiated N, N′-dibenzoyl-1,3-diaminopropan-2-ol

  摘要：

  Tritiated N,N'-dibenzoyl-1,3-diaminopropan-2-ol, a compound mimicking a diacylglycerol moiety used as a lipid drug carrier was prepared from N,N'-dibenzoyl-1,3-diaminopropan-2-ol by isotopic exchange in the presence of rhodium chloride. Preliminary preparation of the deuterated analog was made in order to assess the position of the substitution. A biodistribution study was carried out in mice after intravenous administration. Five minutes after administration, the level found in the brain was about 9 % of the injected dose per g organ. This value decreases to 1 % 3 hours after administration while in the same time radioactive levels measured in the urine increased.The results are in accordance with the pharmacological evaluation : N,N'-dibenzoyl-1,3-diaminopropan-2-ol exhibits an anticonvulsant activity at 30 minutes in the maximal electroshock seizure test, but was found inactive at 3 hours.

  DOI：

  10.1002/(sici)1099-1344(199610)38:10<897::aid-jlcr916>3.0.co;2-d
• 作为产物：
  描述：

  苯甲酰氯 、 1,3-二氨基-2-羟基丙烷 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以34.8%的产率得到N,N'-dibenzoyl-1,3-diaminopropan-2-ol
  参考文献：
  名称：

  Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor

  摘要：

  Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of D-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 mu M and 50 mu M, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.047

文献信息

• A New Simple and Mild Synthesis of 2-Substituted 2-Oxazolines
  作者：Christian Sund、Jyrki Ylikoski、Marek Kwiatkowski

  DOI：10.1055/s-1987-28103

  日期：——

  N-Acylated ß-aminoalcohols were converted to 2-oxazolines under very mild conditions employing commonly used phosphorylating reagents.

  N-酰基化的β-氨基醇在非常温和的条件下，使用常用的磷酸化试剂转化为2-噁唑啉。
• Palladium-Catalyzed Selective Amino- and Alkoxycarbonylation of Iodoarenes with Aliphatic Aminoalcohols as Heterobifunctional O,N-Nucleophiles
  作者：László Kollár、Attila Takács、Csilla Molnár、Andrew Kovács、László T. Mika、Péter Pongrácz

  DOI：10.1021/acs.joc.2c02712

  日期：2023.4.21

  heteroaromatic substrates and numerous related nucleophiles were tested under optimized conditions, providing moderate to good yields of the target compounds. Reactions of serinol and 1,3-diamino-2-propanol as model trifunctional compounds showed particularly high chemoselectivity on amide ester products. Considering the coordinative properties of the applied nucleophiles, a rational catalytic cycle was proposed

  在脂肪族异双功能 N,O-亲核试剂存在的情况下，研究了钯催化的芳基碘化物的氨基和烷氧基羰基化反应。实现了酰胺醇和酰胺酯的选择性合成，由碱和底物的比例控制。还研究了碘苯取代基对产物选择性的影响，结果令人惊讶。除了模型乙醇胺/碘苯系统外，还在优化条件下测试了各种杂芳基底物和许多相关亲核试剂，提供了中等至良好的目标化合物收率。丝氨醇和 1,3-二氨基-2-丙醇作为模型三官能化合物的反应对酰胺酯产物显示出特别高的化学选择性。考虑到所应用的亲核试剂的配位性质，
• Catalytic Amide Activation with Thermally Stable Molybdenum(VI) Dioxide Complexes
  作者：Garrett E. Evenson、Wyatt C. Powell、Aaron B. Hinds、Maciej A. Walczak

  DOI：10.1021/acs.joc.3c00218

  日期：2023.5.5

  practical method of oxazoline and thiazoline formation, which can facilitate the synthesis of natural products, chiral ligands, and pharmaceutical intermediates. This method capitalized on a Mo(VI) dioxide catalyst stabilized by substituted picolinic acid ligands, which is tolerant to many functional groups that would otherwise be sensitive to highly electrophilic alternative reagents.

  恶唑啉和噻唑啉是生物活性天然产物和药物的重要成分。在这里，我们报告了一种有效且实用的恶唑啉和噻唑啉形成方法的开发，该方法可以促进天然产物、手性配体和药物中间体的合成。该方法利用了由取代的吡啶甲酸配体稳定的二氧化钼（VI）催化剂，该催化剂能够耐受许多官能团，否则这些官能团将对高亲电替代试剂敏感。
• SUND, CHRISTIAN;YLIKOSKI, JYRKI;KWIATKOWSKI, MAREK, SYNTHESIS,(1987) N 9, 853-854
  作者：SUND, CHRISTIAN、YLIKOSKI, JYRKI、KWIATKOWSKI, MAREK

  DOI：——

  日期：——
• Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor
  作者：Tihomir Tomašić、David Hajšek、Urban Švajger、Jernej Luzar、Nataša Obermajer、Isabelle Petit-Haertlein、Franck Fieschi、Marko Anderluh

  DOI：10.1016/j.ejmech.2014.01.047

  日期：2014.3

  Dendritic cell-specific, intercellular adhesion molecule-3-grabbing non-integrin (DC-SIGN) is a C-type lectin expressed specifically on dendritic cells. It is a primary site for recognition and binding of various pathogens and thus a promising therapeutic target for inhibition of pathogen entry and subsequent prevention of immune defense cell infection. We report the design and synthesis of D-mannose-based DC-SIGN antagonists bearing diaryl substituted 1,3-diaminopropanol or glycerol moieties incorporated to target the hydrophobic groove of the receptor. The designed glycomimetics were evaluated by in vitro assay of the isolated DC-SIGN extracellular domain for their ability to compete with HIV-1 gp120 for binding to the DC-SIGN carbohydrate recognition domain. Compounds 14d and 14e, that display IC50 values of 40 mu M and 50 mu M, are among the most potent monovalent DC-SIGN antagonists reported. The antagonistic effect of all the synthesized compounds was further evaluated by a one-point in vitro assay that measures DC adhesion. Compounds 14d, 14e, 18d and 18e were shown to act as functional antagonists of DC-SIGN-mediated DC adhesion. The binding mode of 14d was also studied by molecular docking and molecular dynamics simulation, which revealed flexibility of 14d in the binding site and provides a basis for further optimization. (C) 2014 Elsevier Masson SAS. All rights reserved.