N-(4-methoxycarbonylbenzoyloxy)succinimide | 264270-90-8

• 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-(4-methoxycarbonylbenzoyloxy)succinimide
• 英文别名: methyl terephthalate succinimidyl ester；terephthalic acid methyl ONSu ester；2,5-Dioxopyrrolidin-1-yl methyl terephthalate；4-O-(2,5-dioxopyrrolidin-1-yl) 1-O-methyl benzene-1,4-dicarboxylate
• CAS: 264270-90-8
• 化学式: C₁₃H₁₁NO₆
• 分子量: 277.233
• InChiKey: ZPMABXBMGNFHCV-UHFFFAOYSA-N

物化性质

• 沸点：
  428.8±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-methoxycarbonylbenzoyloxy)succinimide 在 caesium carbonate 、 三氟乙酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5'-O-[N-(4-carboxylatobenzoyl)sulfamoyl]cytidine sodium salt
  参考文献：
  名称：

  Sialyltransferase inhibitors: consideration of molecular shape and charge/hydrophobic interactions

  摘要：

  In order to evaluate the importance of molecular shape of inhibitor molecules and the charge/H-bond and hydrophobic interactions, we synthesized three types of molecules and tested them against a sialyltransferase. The first type of compounds were designed as substrate mimics in which the phosphate in CMP-Neu5NAc was replaced by a non-hydrolysable, uncharged 1,2,3-triazole moiety. The second type of compound contained a 2-deoxy-2,3-dehydro-acetylneuraminic moiety which was linked to cytidine through its carboxylic acid and amide linkers. In the third type of compound the sialyl phosphate was substituted by an aryl sulfonamide which was then linked to cytidine. Inhibition study of these cytidine conjugates against Campylobacter jejuni sialyltransferase Cst 06 showed that the first type of molecules are competitive inhibitors, whereas the other two could only inhibit the enzyme non-competitively. The results indicate that although the binding specificity may be guided by molecular shape and H-bond interaction, the charge and hydrophobic interactions contributed most to the binding affinity. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.12.017
• 作为产物：
  描述：

  对甲酰基苯甲酸甲酯 在 potassium permanganate 、 硫酸 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-(4-methoxycarbonylbenzoyloxy)succinimide
  参考文献：
  名称：

  SYNTHESIS AND CHARACTERIZATION OF BIS- AND TOS-(4-CARBOXYBENZOYL)-ALKANEAMINES

  摘要：

  A practical and efficient protocol to obtain bis- and tris-(4-carboxybenzoyl)alkaneamines based on monoprotected 1,4-benzenedicarboxylic acid is reported here. N-(4-methoxycarbonylbenzoyloxy)succinimide was treated with aliphatic diamines and triamines to form aliphatic hydrocarbon-linked bis- and tris-amides 4a-4e. The yields ranged from good to very good and showed that choosing the right acylating agent is a key point in this synthesis. All the compounds were characterized by elemental analysis, FTIR, and H-1 NMR.

  DOI：

  10.4067/s0717-97072012000300023

文献信息

• <i>N</i>-Hydroxysuccinimide-promoted Oxidation of Primary Alcohols and Aldehydes to Form Active Esters with Hypervalent(III) Iodine
  作者：Naiwei Wang、Renhua Liu、Qing Xu、Xinmiao Liang

  DOI：10.1246/cl.2006.566

  日期：2006.6

  A simple, mild, and efficient method for the conversion of primary alcohols and aldehydes to N-hydroxysuccinimide esters with (diacetoxyiodo)benzene in high yield is developed. N-Hydroxysuccinimide acts not only as an esterification partner but also as an activator of PhI(OAc)2 in this reaction.

  开发了一种简单、温和且高效的方法，利用高产率的(二乙酰氧碘)苯将伯醇和醛转化为N-羟基琥珀酰亚胺酯。N-羟基琥珀酰亚胺在此反应中不仅作为酯化伴侣，还作为PhI(OAc)2的活化剂。
• Artificial Molecular Clamp: A Novel Device for Synthetic Polymerases
  作者：Yoshinori Takashima、Motofumi Osaki、Yoshihiro Ishimaru、Hiroyasu Yamaguchi、Akira Harada

  DOI：10.1002/anie.201102834

  日期：2011.8.8

  Synthetic polymerases composed of a cyclodextrin (CD) dimer yield high‐molecular‐weight polymers of cyclic esters without using solvents and co‐catalysts. One CD moiety is attached to the active site of a supramolecular catalyst and propagates the polymerization by serving as artificial molecular clamp (see picture). The other CD moiety initiates the ring‐opening polymerization.

  由环糊精（CD）二聚体组成的合成聚合酶无需使用溶剂和助催化剂即可产生高分子量的环状酯聚合物。一个CD部分连接至超分子催化剂的活性位点，并通过充当人工分子钳位（参见图片）来传播聚合反应。另一个CD部分引发开环聚合。
• Metal-free intermolecular C–O cross-coupling reactions: synthesis of N-hydroxyimide esters
  作者：Yunhe Lv、Kai Sun、Weiya Pu、Shukuan Mao、Gang Li、Jiejie Niu、Qian Chen、Tingting Wang

  DOI：10.1039/c6ra22653a

  日期：——

  Selectfluor-mediated intermolecular C–O cross coupling reaction for the synthesis of N-hydroxyimide esters was developed for the first time. The reaction is applicable to the coupling of readily available aryl and alkyl aldehydes with N-hydroxyphthalimide (NHPI) and N-hydroxysuccinimide (NHSI). The resulting active esters can be directly converted into amides in one pot.

  首次开发了Selectfluor介导的分子间C–O交叉偶联反应，用于合成N-羟基酰亚胺酯。该反应适用于容易获得的芳基和烷基醛与N-羟基邻苯二甲酰亚胺（NHPI）和N-羟基琥珀酰亚胺（NHSI）的偶联。可以在一锅中将所得的活性酯直接转化为酰胺。
• Interfacial and Nanoconfinement Effects Decrease the Excited-State Acidity of Polymer-Bound Photoacids
  作者：Christopher D. Sanborn、Jenu Varghese Chacko、Michelle Digman、Shane Ardo

  DOI：10.1016/j.chempr.2019.04.022

  日期：2019.6

  photoacid-modified polymers, which generate hydrated protons in response to visible-light excitation. Pyrenol photoacid dye molecules were covalently bonded within conical nanopores that had been track etched in poly(ethylene terephthalate). The data suggest that ∼90% of the nanopore surfaces were modified with photoacids and that photoacids were, on average, bound through three sulfonamide groups. In comparison

  纳米级的光引发离子迁移与包括能量转换，神经元触发和仿生过程在内的各个领域有关。为了研究这种现象，我们合成并评估了光酸改性的聚合物，该聚合物可响应可见光激发而生成水合质子。苯酚光酸染料分子共价键合在锥形纳米孔内，该纳米孔已在聚对苯二甲酸乙二醇酯中被蚀刻。数据表明，约90％的纳米孔表面被光酸修饰，并且光酸平均通过三个磺酰胺基团结合。与溶解在水溶液中的光酸相比，专门结合到纳米孔尖端区域的光酸在其基态和激发态下平均而言是较弱的酸，我们推测这是由于受限纳米孔中表面电势或溶剂化环境的差异所致。这些结果表明，由纳米限制的光酸引发的离子迁移将需要仔细的分子工程，以实现有效的光能到离子能的转换。
• Functional materials from the covalent modification of reduced graphene oxide and β-cyclodextrin as a drug delivery carrier
  作者：Guangcheng Wei、Renhao Dong、Dong Wang、Lei Feng、Shuli Dong、Aixin Song、Jingcheng Hao

  DOI：10.1039/c3nj00690e

  日期：——

  We report a drug delivery system based on the covalently reduced graphene oxide (rGO) with p-aminobenzoic acid (rGO-C6H4-COOH) for the loading and targeted delivery of the anticancer drug, doxorubicin (DOX). The colloidal solution of rGO-C6H4-COOH conjugated by polyethyleneimine (PEI) and Biotin was prepared. This endows the colloidal solution of rGO-C6H4-CO-NH-PEI-NH-CO-Biotin, which presents excellent water-solubility and targeting as a drug delivery system. β-Cyclodextrin (β-CD) molecules, which are host molecules for accommodating guest molecules, such as water insoluble anticancer drugs, were introduced to reduce the cytotoxicity of the drug delivery system and to improve the biocompatibility. The drug delivery of rGO-C6H4-CO-NH-PEI-NH-CO-CD-Biotin has a ∼24.64% drug (DOX) loading ratio. The drug release behavior was pH dependent at higher DOX concentrations, but salt dependent at lower DOX concentrations, which could be exploited for controlled drug release in cancer cells. The DOX loaded on rGO-C6H4-CO-NH-PEI-NH-CO-CD-Biotin could effectively induce HepG2 cancer cell apoptosis. This can be explained by the conjugation of DOX and rGO-C6H4-CO-NH-PEI-NH-CO-CD-Biotin being able to arrest the cancer cells in the G2 phase, which is the most sensitive to the anticancer drug.

  我们报告了一种基于对氨基苯甲酸共价还原氧化石墨烯（rGO）（rGO-C6H4-COOH）的给药系统，用于负载和靶向输送抗癌药物多柔比星（DOX）。制备了由聚乙烯亚胺（PEI）和生物素共轭的 rGO-C6H4-COOH 胶体溶液。这种rGO-C6H4-CO-NH-PEI-NH-CO-生物素胶体溶液具有优异的水溶性和靶向性，可作为一种药物输送系统。δ-环糊精（δ-CD）分子是容纳客体分子（如水不溶性抗癌药物）的宿主分子，它的引入降低了给药系统的细胞毒性，提高了生物相容性。rGO-C6H4-CO-NH-PEI-NH-CO-CD-生物素的药物释放率为±24.64%。在较高的DOX浓度下，药物释放行为与pH值有关，而在较低的DOX浓度下，药物释放行为与盐有关。负载在 rGO-C6H4-CO-NH-PEI-NH-CO-CD-Biotin 上的 DOX 能有效诱导 HepG2 癌细胞凋亡。这是因为 DOX 与 rGO-C6H4-CO-NH-PEI-NH-CO-CD-Biotin 的共轭作用能够使癌细胞停滞在对抗癌药物最敏感的 G2 期。