3,5-diamino-N-(3,4-dihydroxyphenethyl)benzamide | 1269758-44-2

• 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: 3,5-diamino-N-(3,4-dihydroxyphenethyl)benzamide
• 英文别名: 3,5-diamino-N-[2-(3,4-dihydroxyphenyl)ethyl]benzamide
• CAS: 1269758-44-2
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: NSGAOQWBIFDADD-UHFFFAOYSA-N

物化性质

• 沸点：
  614.7±55.0 °C(Predicted)
• 密度：
  1.378±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  122
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以70%的产率得到3,5-diamino-N-(3,4-dihydroxyphenethyl)benzamide
  参考文献：
  名称：

  天然产物去氢二氢瓜二酸的结构优化，以发现新型类似物作为AcrB抑制剂。

  摘要：

  药物外排泵对危险的细菌病原体具有多重耐药性，这使这些蛋白质成为有希望的药物靶标。在本文中，我们围绕先前描述的外排泵抑制剂降冰片二氢乙酸（NDGA）提出了初始化学优化和结构-活性关系（SAR）数据。设计，合成和评估了针对大肠杆菌AcrB的四个系列的新型NDGA类似物，以评估它们增强抗生素活性，抑制AcrB介导的底物外流并降低脱靶活性的能力。鉴定出九种新颖结构，这些结构提高了一组抗生素的功效，抑制了药物外排并降低了细菌外膜和内膜的通透性。其中，WA7，具有广谱抗菌增敏活性的WB11和WD6被鉴定为具有良好特性的NDGA类似物，可作为潜在的AcrB抑制剂，与NDGA相比，其效能有中等程度的提高。尤其是，WD6是最广泛活性的类似物，可提高所有四类抗菌药物的活性。

  DOI：

  10.1016/j.ejmech.2019.111910

文献信息

• Synthesis of novel nanostructured chiral poly(amide-imide)s containing dopamine and natural amino acids
  作者：Shadpour Mallakpour、Amin Zadehnazari

  DOI：10.1007/s12039-012-0351-0

  日期：2013.1

  Four new thermally stable and optically active poly(amide-imide)s (PAI)s with good inherent viscosities were synthesized from the direct polycondensation reaction of N,N′-(pyromellitoyl)-bis-L-α-amino acids with 3,5-diamino-N-(3,4-dihydroxy-phen-ethyl)benzamide in a medium consisting of a molten salt, tetrabutylammonium bromide, and triphenyl phosphite as the activator. The polymerization reactions

  通过N，N ' -（均苯四甲酰基）-双-L - α-氨基酸与3，N，N '的直接缩聚反应合成了四种具有良好固有粘度的新型热稳定且光学活性的聚（酰胺-酰亚胺）（PAI）。在由熔融盐，四丁基溴化铵和亚磷酸三苯酯作为活化剂组成的介质中的5-二氨基-N-（3,4-二羟基-苯乙基）苯甲酰胺 聚合反应以高收率生产了一系列新型PAI，PAA在侧链中包含多巴胺链段，固有粘度在0.33至0.49 dL / g之间。所得聚合物通常通过FT-IR 1表征。1 H NMR光谱，元素分析，粉末X射线衍射，场发射扫描电子显微镜，比浓对数粘度和溶解度测试。还使用热重分析（TGA和DTG）和极限氧指数（LOI）研究了PAI的热性能和阻燃性能。通过热分析获得的数据表明这些聚合物表现出良好的热稳定性。此外，TGA的高炭收率和良好的LOI值表明所获得的聚合物能够表现出良好的阻燃性能。 通过3,5-二氨基-N-（3,4-二羟基苯
• Synthesis, morphology investigation and thermal mechanical properties of dopamine-functionalized multi-walled carbon nanotube/poly(amide-imide) composites
  作者：Shadpour Mallakpour、Amin Zadehnazari

  DOI：10.1016/j.reactfunctpolym.2016.07.010

  日期：2016.9

  Here, poly(amide-imide) (PAI) composites containing multi-walled carbon nanotubes (MWCNT) were synthesized with solution casting method. To improve the dispersion and compatibility with the polymer matrix the MWCNT was surface-modified with dopamine biomolecule under microwave irradiation. The prepared dopamine-functionalized MWCNT (MWCNT-Dop) was characterized for their structure, morphology, and thermal

  在此，通过溶液浇铸法合成了含有多壁碳纳米管（MWCNT）的聚（酰胺-酰亚胺）（PAI）复合材料。为了改善分散性和与聚合物基质的相容性，在微波辐射下用多巴胺生物分子对MWCNT进行了表面改性。使用傅立叶变换红外光谱（FT-IR），X射线衍射（XRD），热重分析，场发射扫描电子显微镜（FTIR）对制备的多巴胺官能化的MWCNT（MWCNT-Dop）的结构，形态和热行为进行表征FE-SEM）和透射电子显微镜（TEM）。结果一致证实了在MWCNT上多巴胺官能团的形成。MWCNT-Dop / PAI杂化膜还使用FT-IR和XRD技术进行了广泛表征。通过FE-SEM和TEM研究了复合材料的微观结构，包括纳米管的分散状态和聚合物-纳米管的界面。还研究了所得复合材料的热行为和机械性能。与纯PAI相比，MWCNT-Dop增强复合材料具有更高的热稳定性，拉伸强度和杨氏模量。
• NANOSTRUCTURE FORMATION IN CHIRAL POLY(AMIDE-IMIDE)S BASED ON DOPAMINE MOIETY AND N-TRIMELLITYLIMIDO-L-AMINO ACIDS IN THE MAIN CHAIN
  作者：S MALLAKPOUR、A ZADEHNAZARI

  DOI：10.4067/s0717-97072012000300011

  日期：——

  Nanostructured poly(amide-imide) (PAI) materials have been produced by polymerizing a diamine monomer, 3,5-diamino-N-(3,4-dihydroxyphenethyl) benzamide, with four trimellitic anhydride-derived, imide ring-preformed chiral amino acid-based dicarboxylic acids. Polycondensation reactions were carried out in the presence of small amount of molten tetrabutylammonium bromide as a green molten salt medium and triphenyl phosphite as the activator by classical heating method. Field emission scanning electron microscopy micrographs showed that the prepared polymers are assembled by spherical particles, which are distributed uniformly and randomly, having nano-sized diameter ranged between 46-54 nm. According to X-ray diffraction patterns, all of PAIs are amorphous. They show excellent solubility in a variety of amide polar solvents and even in less polar solvents such as m-cresol and pyridine. The obtained PAIs were also characterized by Fourier transform infrared spectroscopy, H-1 NMR, elemental, and thermogravimetric analysis techniques. The effect of ultrasound on the morphology of polymers was also investigated. This study confirmed that the size of polymer particles was decreased and the shape of them was also changed.
• Synthesis and characterization of novel dopamine-derivative: Application of modified multi-wall carbon nanotubes paste electrode for electrochemical investigation
  作者：Shadpour Mallakpour、Mehdi Hatami、Ali A. Ensafi、Hassan Karimi-Maleh

  DOI：10.1016/j.cclet.2010.07.031

  日期：2011.2

  Novel dopamine-derivative compound, 3,5-diamino-N-(3,4-dihydroxyphenethyl)benzamide (3,5-DAB) was prepared in two steps. In the first step dopamine hydrochloride was reacted with 3,5-dinitrobenzoyl chloride in the presence of propylene oxide. In the second step reduction of nitro groups resulted in preparation of 3,5-DAB in quantitative yield. This material was characterized using conventional spectroscopic methods such as FT-IR and H-1 NMR. In addition, the redox response of a modified carbon nanotubes paste electrode of 3,5-DAB was investigated in aqueous solution at a neutral pH. The result showed that the electrode process has a quasi-reversible response, with Delta E-P, greater than the (59/n) mV expected for a reversible system. Finally, the diffusion coefficient for redox process in paraffin oil matrix obtained using chronoamperometry methods. (C) 2010 Shadpour Mallakpour. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.