methyl 2-[(4-nitrophenyl)sulfonylamino]acetate

• 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: methyl 2-[(4-nitrophenyl)sulfonylamino]acetate
• 英文别名: methyl (4-nitrophenylsulfonylamino)acetate；methyl 2-(4-nitrophenylsulfonamido)acetate；pNBS-Gly-OMe；Methyl 2-{[(4-nitrophenyl)sulfonyl]amino}acetate
• 化学式: C₉H₁₀N₂O₆S
• mdl: MFCD00446722
• 分子量: 274.254
• InChiKey: JHCNCYASDRYDIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-[(4-nitrophenyl)sulfonylamino]acetate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 {[(4-氨基苯基)磺酰基]氨基}乙酸甲酯
  参考文献：
  名称：

  An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors

  摘要：

  ATP competitive inhibitors of DNA gyrase and topoisomerase IV have great therapeutic potential, but none of the described synthetic compounds has so far reached the market. To optimise the activities and physicochemical properties of our previously reported N-phenylpyrrolamide inhibitors, we have synthesized an improved, chemically variegated selection of compounds and evaluated them against DNA gyrase and topoisomerase IV enzymes, and against selected Gram-positive and Gram-negative bacteria. The most potent compound displayed IC50 values of 6.9 nM against Escherichia coli DNA gyrase and 960 nM against Staphylococcus aureus topoisomerase IV. Several compounds displayed minimum inhibitory concentrations (MICs) against Gram-positive strains in the 1-50 mu M range, one of which inhibited the growth of Enterococcus faecalis, Enterococcus faecium, S. aureus and Streptococcus pyogenes with MIC values of 1.56 mu M, 1.56 mu M, 0.78 mu M and 0.72 mu M, respectively. This compound has been investigated further on methicillin-resistant S. aureus (MRSA) and on ciprofloxacin non-susceptible and extremely drug resistant strain of S. aureus (MRSA VISA). It exhibited the MIC value of 2.5 mu M on both strains, and MIC value of 32 mu M against MRSA in the presence of inactivated human blood serum. Further studies are needed to confirm its mode of action. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.02.004
• 作为产物：
  描述：

  对硝基苯磺酰氯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 methyl 2-[(4-nitrophenyl)sulfonylamino]acetate
  参考文献：
  名称：

  通过 Oxyma-O-磺酸盐合成磺酰胺 - 与酸敏感基团和固相肽合成的兼容性

  摘要：

  报道了一种通过将磺酸基活化为相应的 2-氰基-2-(羟基亚氨基)乙酸乙酯 (Oxyma) 磺酸酯来合成磺胺类药物的更温和、更有效的方法。为此，此方法比所有其他现有协议更环保。其他重要优势在于 (a) 在环境和温和条件下适用于亲核性较低的苯胺，以及 (b) 与固相肽合成和酸不稳定基团如三苯甲基 (Trt) 和 tBu 的相容性，这使固相合成成为可能各种肽的磺胺类药物。为了说明这一点，使用基于 Fmoc 的固相肽合成 (SPPS) 证明了肽 GAILG-NH2 的三种磺酰胺衍生物的合成，这与治疗 2 型糖尿病的药物设计相关。

  DOI：

  10.1002/ejoc.201201571

文献信息

• Modular sub-monomeric cell-penetrating guanidine-rich peptoids – synthesis, assembly and biological evaluation
  作者：Etienne Marouseau、Albane Neckebroeck、Heidi Larkin、Antoine Le Roux、Leonid Volkov、Christine L. Lavoie、Éric Marsault

  DOI：10.1039/c6ra27898a

  日期：——

  membranes. This article reports the synthesis of a modular, conformationally restricted guanidinium display scaffold, designed with the goal to study the impact of conformational restrictions on the resulting properties of the transporters and ultimately probe the anionic chemical space of the cellular membrane. The scaffold was assembled on solid phase as a peptoid, and its subsequent biological evaluation

  富含胍基的转运蛋白是有望通过细胞膜传递多种分子的试剂。本文报道了模块化的，构象受限的胍盐展示支架的合成，其目的是研究构象限制对转运蛋白最终性质的影响，并最终探查细胞膜的阴离子化学空间。该支架以类肽的形式固相组装，其随后的生物学评估显示细胞渗透性非常好，细胞毒性也很低。
• Sulfonamide Synthesis via Oxyma-<i>O</i>-sulfonates - Compatibility to Acid Sensitive Groups and Solid-Phase Peptide Synthesis
  作者：Nani Babu Palakurthy、Dharm Dev、Shubhasmin Rana、Krishna Chaitanya Nadimpally、Bhubaneswar Mandal

  DOI：10.1002/ejoc.201201571

  日期：2013.5

  solid phase peptide synthesis and acid-labile groups such as trityl (Trt) and tBu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG-NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc-based solid-phase peptide synthesis (SPPS).

  报道了一种通过将磺酸基活化为相应的 2-氰基-2-(羟基亚氨基)乙酸乙酯 (Oxyma) 磺酸酯来合成磺胺类药物的更温和、更有效的方法。为此，此方法比所有其他现有协议更环保。其他重要优势在于 (a) 在环境和温和条件下适用于亲核性较低的苯胺，以及 (b) 与固相肽合成和酸不稳定基团如三苯甲基 (Trt) 和 tBu 的相容性，这使固相合成成为可能各种肽的磺胺类药物。为了说明这一点，使用基于 Fmoc 的固相肽合成 (SPPS) 证明了肽 GAILG-NH2 的三种磺酰胺衍生物的合成，这与治疗 2 型糖尿病的药物设计相关。
• Synthesis of α‐Aryl Acrylamides via Lewis‐Base‐Mediated Aryl/Hydrogen Exchange
  作者：Miran Lemmerer、Haoqi Zhang、Anthony J. Fernandes、Tobias Fischer、Marianne Mießkes、Yi Xiao、Nuno Maulide

  DOI：10.1002/anie.202207475

  日期：2022.10.4

  A DABCO-induced polar aryl migration allows for the synthesis of α-aryl acrylamides from sulfonyl acrylimides. This reaction proceeds through a formal aryl/hydrogen exchange, including SO2 loss. A range of valuable building blocks have been synthesised and the underlying reaction mechanism has been explored using quantum chemical calculations.

  DABCO 诱导的极性芳基迁移允许从磺酰丙烯酰亚胺合成 α-芳基丙烯酰胺。该反应通过正式的芳基/氢交换进行，包括SO 2损失。一系列有价值的构建模块已经被合成，并使用量子化学计算探索了潜在的反应机制。
• [EN] CREATINE PRODRUGS, COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] PROMÉDICAMENTS À BASE DE CRÉATINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：ULTRAGENYX PHARMACEUTICAL INC

  公开号：WO2019109067A3

  公开（公告）日：2020-03-26
• Synthesis of Cyclic Dipeptides by Ring-Closing Metathesis
  作者：John F. Reichwein、Rob M. J. Liskamp

  DOI：10.1002/1099-0690(200006)2000:12<2335::aid-ejoc2335>3.0.co;2-c

  日期：2000.6

  Several cyclic dipeptides (4a-g and 9a-c) have been synthesized by "amide-to-amide" cyclization of 2a-g and 8a-c, respectively, by means of ring-closing metathesis employing the Grubbs ruthenium catalyst. The influence of additives as well as the length of the amide substituent were studied. Best yields were obtained by cyclization in solution with either lithium fluoroacetate or alpha,alpha-dichlorotoluene as an additive.