N-hydroxymethyl-3-nitrophthalimide | 22546-83-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-hydroxymethyl-3-nitrophthalimide
• 英文别名: 2-hydroxymethyl-5-nitro-isoindoline-1,3-dione；2-Hydroxymethyl-5-nitro-isoindolin-1,3-dion；N-Hydroxymethyl-4-nitrophthalimid；2-(Hydroxymethyl)-5-nitroisoindoline-1,3-dione；2-(hydroxymethyl)-5-nitroisoindole-1,3-dione
• CAS: 22546-83-4
• 化学式: C₉H₆N₂O₅
• mdl: MFCD00023076
• 分子量: 222.157
• InChiKey: LCUYVSBMPMKCST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-hydroxymethyl-3-nitrophthalimide 在 盐酸 、 硫酸 、 palladium on activated charcoal 、 硝酸 、 甲酸铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.0h， 生成 2-Hydroxy-5-[[5-[(4-methylphenyl)sulfonylamino]-1,3-dioxoisoindol-2-yl]methyl]benzoic acid
  参考文献：
  名称：

  A new series of N2-substituted-5-(p-toluenesulfonylamino)phthalimide analogues as α-glucosidase inhibitors

  摘要：

  Several members of a new family of non-sugar-type alpha-glycosidase inhibitors, bearing a 5-(p-toluenesulfonylamino)phthalimide moiety and various substituent at the N2 position, were synthesized and their activities were investigated. The newly synthesized compounds displayed different inhibition profile towards yeast alpha-glycosidase and rat intestinal alpha-glycosidase. Almost all the compounds had strong inhibitory activities against yeast alpha-glycosidase. Regarding rat intestinal alpha-glycosidase, only analogs with N2-aromatic substituents displayed varying degrees of inhibitory activities on rat intestinal maltase and lactase and nearly all compounds showed no inhibition against rat intestinal alpha-amylase. Structure-activity relationship studies indicated that 5-(p-toluenesulfonylamino)phthalimide moiety is a favorable scaffold to exert the alpha-glucosidase inhibitory activity and substituents at the N2 position have considerable influence on the efficacy of the inhibition activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.011
• 作为产物：
  描述：

  4-硝基邻苯二甲酸酐 在 formamide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 N-hydroxymethyl-3-nitrophthalimide
  参考文献：
  名称：

  快速方便的微波辅助合成芳香族酰亚胺和 N-羟甲基酰亚胺

  摘要：

  摘要 报道了极其简单的高产率和快速微波辅助合成多种芳香族单亚胺和二亚胺以及单-和双-N-羟甲基亚胺。

  DOI：

  10.1081/scc-120018768

文献信息

• Isoindole-1,3-dione derivatives as RSK2 inhibitors: synthesis, molecular docking simulation and SAR analysis
  作者：Wei Zhou、Shiliang Li、Weiqiang Lu、Jun Yuan、Yufang Xu、Honglin Li、Jin Huang、Zhenjiang Zhao

  DOI：10.1039/c5md00469a

  日期：——

  RSK2 (p90 ribosomal S6 kinase 2) is a serine/threonine kinase expressed in a variety of cancers. Molecular-targeted inhibition of RSK2 as a potential therapeutic strategy for human cancers has been documented. In this work, a series of isoindole-1,3-dione derivatives as novel RSK2 inhibitors were designed and synthesized from a hit discovered in our previous study. Some compounds were confirmed to

  RSK2（p90核糖体S6激酶2）是在多种癌症中表达的丝氨酸/苏氨酸激酶。已经证明了分子靶向抑制RSK2作为人类癌症的潜在治疗策略。在这项工作中，从我们先前的研究中发现的命中物中，设计并合成了一系列新型RSK2抑制剂异吲哚-1,3-二酮衍生物。已确认某些化合物是中等有效的RSK2抑制剂，IC 50值约为0.5μM。通过分子对接进行结构-活性关系分析和结合模式研究。
• Asymmetric Organocatalyzed Transfer Hydroxymethylation of Isoindolinones Using Formaldehyde Surrogates
  作者：David Svestka、Pavel Bobal、Mario Waser、Jan Otevrel

  DOI：10.1021/acs.orglett.4c00818

  日期：2024.3.29

  asymmetric transfer hydroxymethylation of activated isoindolinones, allowing us to prepare the enantioenriched hydroxymethylated adducts in good to excellent yields (48–96%) and enantiopurities (81:19–97:3 e.r.). To increase the reaction rate without compromising the selectivity, carefully optimized formaldehyde surrogates were employed, providing a convenient source of anhydrous formaldehyde with a base-triggered

  基于哌啶的竹本催化剂已成功用于活化异吲哚啉酮的新型不对称转移羟甲基化，使我们能够以良好至优异的产率（48-96%）和对映体纯度（81:19-97:3 er）制备对映体富集的羟甲基化加合物。 ）。为了在不影响选择性的情况下提高反应速率，采用了仔细优化的甲醛替代物，提供了具有碱触发释放的无水甲醛的便捷来源。底物范围包括 34 个条目，显示了不对称转化的相当普遍性，大多数条目在 24-48 小时内表现出完全转化。还进行了放大实验和多个对映选择性下游转化，表明了产品的预期合成效用。
• Billman; Cash, Proceedings of the Indiana Academy of Science, 1953, vol. 63, p. 108
  作者：Billman、Cash

  DOI：——

  日期：——
• Application of Ultrasound Irradiation for the Reactions of N-Hydroxymethylation
  作者：Wujun Zhong、Gonghua Song、Yanqing Peng、Xuhong Qian

  DOI：10.1080/00397910008087009

  日期：2000.10

  A convenient and high yield method for the N-hydroxymethylation of substituted phthalimide and benzimidazole under ultrasound irradiation is reported.
• Vasa; Kshatriya, Journal of the Indian Chemical Society, 1959, vol. 36, p. 527
  作者：Vasa、Kshatriya

  DOI：——

  日期：——