N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine | 1037569-82-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine
• 英文别名: N-[N-(3,5-Dinitro-benzoyl)-glycyl]-glycin；2-[[2-[(3,5-Dinitrobenzoyl)amino]acetyl]amino]acetic acid
• CAS: 1037569-82-6
• 化学式: C₁₁H₁₀N₄O₈
• 分子量: 326.222
• InChiKey: UAUSINFAGCCZNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,3'-二氨基二丙基胺 、 N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以51%的产率得到N-[2-[[2-[3-[3-[[2-[[2-[(3,5-dinitrobenzoyl)amino]acetyl]amino]acetyl]amino]propylamino]propylamino]-2-oxoethyl]amino]-2-oxoethyl]-3,5-dinitrobenzamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of glycine-based molecular tongs as inhibitors of Aβ1–40 aggregation in vitro

  摘要：

  A series of N-terminus benzamides of glycine-based symmetric peptides, linked to m-xylylenediamine and 3,4'-oxydianiline spacers, were prepared and tested as inhibitors of beta-amyloid peptide A beta(1 - 40) aggregation in vitro. Compounds with good anti-aggregating activity were detected. Polyphenolic amides showed the highest anti-aggregating activity, with IC50 values in the micromolar range. Structure - activity relationships suggested that pi - pi stacking and hydrogen-bonding interactions play a key role in the inhibition of A beta(1 - 40) self-assembly leading to amyloid fibrils. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.052
• 作为产物：
  描述：

  3,5-二硝基苯甲酰氯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine
  参考文献：
  名称：

  Saunders, Journal of the Chemical Society, 1938, p. 1400

  摘要：

  DOI：

文献信息

• Kinetic Study on Nucleophilic Displacement Reactions of 2-Chloro-4-Nitrophenyl X-Substituted-Benzoates with Primary Amines: Reaction Mechanism and Origin of the α-Effect
  作者：Tae-Il Um、Min-Young Kim、Tae-Eun Kim、Ik-Hwan Um

  DOI：10.5012/bkcs.2014.35.2.436

  日期：2014.2.20

  8.31 13.96 hydrazine 8.20 6627 glycine ethyl ester 7.68 7.068 1,2-diaminopropane-H + 7.13 4.459 trifluoroethylamine 5.68 0.124 Figure 1. Bronsted-type plot for the reactions of 2-chloro-4-nitro-phenyl benzoate ( 1d ) with primary amines in 80 mol % of H 2 O/20mol % DMSO at 25.0 ± 0.1 o C. The identity of points is given inTable 1, and hydrazine is excluded in the correlation. Table 2. Summary of Second-Order

  在 80 mol % $H_2O/20$ mol % DMSO 溶液中，于 $25.0^\circ}C$.2-chloro-4-nitrophenyl benzoate (1d) 与一系列伯胺反应的 Br$emptyset}$nsted-type plot 曲线向下，这被认为是速率决定级（RDS）发生变化的阶梯机理的证据。1a-h 与肼和甘氨酰甘氨酸反应的 Hammett 图是非线性的，而 Yukawa-Tsuno 图则表现出很好的线性关系，$\yrho}_X=1.22-1.35$ 和 $\gamma}= 0.57-0.59$，这表明非线性哈米特图不是由于 RDS 的变化造成的，而是通过 EDG 与基质的 C=O 键之间的共振相互作用，使具有电子供体基团 (EDG) 的基质稳定下来造成的。随着取代基 X 从强 EDG 转变为强电子抽离基 (EWG)，肼表现出的 $\alpha}$ 效应也随之增加。研究得出的结论是，通过相邻非键电子之间的电子斥力使肼失稳并不是取代基依赖性 $\alpha}$ 效应的唯一原因，过渡态的稳定也是 $\alpha}$ 效应的一个合理来源。
• An unusual ground-state stabilization effect and origins of the alpha-effect in aminolyses of Y-substituted phenyl X-substituted benzoates
  作者：Ik-Hwan Um、Eun-Kyung Chung、So-Mi Lee

  DOI：10.1139/cjc-76-6-729

  日期：——

  Second-order rate constants have been measured spectrophotometrically for the reactions of X-C6H4CO2C6H4-Y with a series of primary amines in H2O containing 20 mol% DMSO at 25.0 +/- 0.1 degrees C. The reactivity increases as the substituent (X and Y) becomes a stronger electron-withdrawing group. The sigma(+) constants give better Hammett correlation than sigma constants for the reactions of 4-nitrophenyl X-substituted benzoates with glycylglycine (glygly) and hydrazine (NH2NH3, indicating that the ground-state stabilization effect is unusually significant on the reaction rates. The reactions of X-C6H4CO2C6H4-Y with glygly and NH2NH2 appear to proceed through the same mechanism, but the degree of leaving-group departure and the negative charge developed in the acyl moiety at the rate-determining TS is considered to be more significant for the glygly system than the NH2NH2 system based on beta(1g) and rho(x) values. The magnitude of the alpha-effect is observed to be not always dependent on the beta(nuc) value but dependent on the electronic nature of the substituent X and Y, i.e., an electron-donating substituent increases the alpha-effect, while an electron-withdrawing one decreases the alpha-effect. The present study has led to the conclusion that the ground-state effect is important for the reaction rates but it is not solely responsible for the alpha-effect, and the intramolecular H-bonding interactions (4) are proposed for the cause of the increasing or decreasing a-effect trends observed in the present system.