N,N',N''-tris(carboxymethyl)-1,3,5-benzenetricarboxamide | 182002-00-2

• 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: N,N',N''-tris(carboxymethyl)-1,3,5-benzenetricarboxamide
• 英文别名: benzene-1,3,5-tricarbamido-N,N,N-tris(acetic acid)；2-[[3,5-bis(carboxymethylcarbamoyl)benzoyl]amino]acetic acid
• CAS: 182002-00-2
• 化学式: C₁₅H₁₅N₃O₉
• 分子量: 381.299
• InChiKey: FZDSXGHFAXULPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  226 °C
• 沸点：
  890.4±65.0 °C(predicted)
• 密度：
  1.563±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  199
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N',N''-tris(carboxymethyl)-1,3,5-benzenetricarboxamide 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1-N,3-N,5-N-tris[2-oxo-2-[2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethylamino]ethyl]benzene-1,3,5-tricarboxamide
  参考文献：
  名称：

  含碳水化合物的树枝状大分子的合成。5.使用未保护的碳水化合物制备树枝状聚合物

  摘要：

  含碳水化合物的树枝状聚合物已使用会聚生长方法使用完全未保护的碳水化合物制备。使用酰胺键形成方法，可以轻松合成低代树状聚合物，从而无需使用对糖基残基的保护基操作，即可获得密堆积的糖类树状聚合物。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01548-7
• 作为产物：
  描述：

  ethyl 2-[[3,5-bis[(2-ethoxy-2-oxoethyl)carbamoyl]benzoyl]amino]acetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90%的产率得到N,N',N''-tris(carboxymethyl)-1,3,5-benzenetricarboxamide
  参考文献：
  名称：

  Dodziuk; Demchuk; Kozminski, Polish Journal of Chemistry, 2003, vol. 77, # 3, p. 333 - 340

  摘要：

  DOI：

文献信息

• Ashton, Peter R.; Boyd, Sue E.; Brown, Christopher L., Chemistry - A European Journal, 1996, vol. 2, # 9, p. 1115 - 1128
  作者：Ashton, Peter R.、Boyd, Sue E.、Brown, Christopher L.、Jayaraman, Narayanaswamy、Nepogodiev, Sergey A.、Stoddart, J. Fraser

  DOI：——

  日期：——
• Mimicry of High-Density Lipoprotein: Functional Peptide–Lipid Nanoparticles Based on Multivalent Peptide Constructs
  作者：Yannan Zhao、Tomohiro Imura、Luke J. Leman、Linda K. Curtiss、Bruce E. Maryanoff、M. Reza Ghadiri

  DOI：10.1021/ja404714a

  日期：2013.9.11

  We describe an approach for engineering peptide lipid nanoparticles that function similarly to high-density lipoprotein (HDL). Branched, multivalent constructs, bearing multiple 23- or 16-amino-acid peptides, were designed, synthesized, and combined with phospholipids to produce nanometer-scale discoidal HDL-like particles. A variety of biophysical techniques were employed to characterize the constructs, including size exclusion chromatography, analytical ultracentrifuge sedimentation, circular dichroism, transmission electron microscopy, and fluorescence spectroscopy. The nanoparticles functioned in vitro (human and mouse plasma) and in vivo (mice) to rapidly remodel large native HDLs into small lipid-poor HDL particles, which are key acceptors of cholesterol in reverse cholesterol transport. Fluorescent labeling studies showed that the constituents of the nanoparticles readily distributed into native HDLs, such that the peptide constructs coexisted with apolipoprotein A-I (apoA-I), the main structural protein in HDLs. Importantly, nanolipid particles containing multivalent peptides promoted efficient. cellular cholesterol efflux and were functionally superior to those derived from monomeric apoA-I mimetic peptides. The multivalent peptide lipid nanoparticles were also remarkably stable toward enzymatic digestion in vitro and displayed long half-lives and desirable pharmacokinetic profiles in mice, providing a real practical advantage over previously studied linear or tandem helical peptides. Encouragingly, a two-week exploratory efficacy study in a widely used animal model for atherosclerosis research (LDLr-null mice) using nanoparticles constructed from a trimeric peptide demonstrated an exceptional 50% reduction in the plasma total cholesterol levels compared to the control group. Altogether, the studies reported here point to an attractive avenue for designing synthetic, HDL-like nanoparticles, with potential for treating atherosclerosis.
• Two pseudopolymorphs derived from alkaline earth metals and the pseudopeptidic ligand trimesoyl-tris-glycine
  作者：Vassiliki N. Dokorou、Annie K. Powell、George E. Kostakis

  DOI：10.1016/j.poly.2012.08.032

  日期：2013.3

  The reaction of Ca(NO3)(2)center dot 3H(2)O and Sr(NO3)(2) with trimesoyl-tris-glycine (H3L) leads to a two dimensional (2D) [Ca-2(HL)(2)(mu-H2O)(H2O)(5)]center dot 3H(2)O (1) and a three dimensional (3D) [Sr-2(HL)(2)(H2O)(7)]center dot H2P (2) coordination polymer, respectively, illustrating the substantial influence of the ionic radii of the alkaline earth metals in determining the motif of the final product. (C) 2012 Elsevier Ltd. All rights reserved.
• ——
  作者：Bing Gong、Chong Zheng、Yinfa Yan

  DOI：10.1023/a:1009511501537

  日期：——

  The title compound, C15H15N3O9. 3H(2)O, crystallizes in the centrosymmetric space group R (3) over bar with a = 13.642(5), b = 13.642(5), c = 18.692(5) Angstrom, D-calc, = 1.440 g cm(3), and z = 6. An extensive three-dimensional hydrogen bonded network is observed. The network arises from 15 hydrogen bonds per asymmetric unit. Six identical N-H ... O hydrogen bonds are formed between two triacid molecules, which results in the face-to-face dimerization of the two triacid molecules. The dimers form extended sheets through hydrogen bond interaction with water molecules. The sheets are held together by hydrogen bonds via the water molecules. The planes of the benzenoid ring are parallel to each other.
• Synthesis and anti-leishmanial activity of TRIS-glycine-β-alanine dipeptidic triazole dendron coated with nonameric mannoside glycocluster
  作者：Sushil V. Pawar、Puspesh K. Upadhyay、Sachin Burade、Navanath Kumbhar、Rajendra Patil、Dilip D. Dhavale

  DOI：10.1016/j.carres.2019.107815

  日期：2019.11

  Tripodal nonameric mannoside glycodendrimer 1 with carbohydrate tethered triazole linked with the TRIS-glycine-beta-alanine dipeptidic aromatic centered core was synthesized. Glycodendrimer 1 demonstrated potential in vitro anti-leishmanial activity. The bio-activity data was substantiated with molecular modelling and docking studies of 1 with the three-dimensional protein structure of Leishmanolysin.