N-[(2,4-Dimethoxyphenyl)methyl]phthalimide | 216067-79-7

• 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-[(2,4-Dimethoxyphenyl)methyl]phthalimide
• 英文别名: N-(2,4-dimethoxybenzyloxy)phthalimide；2-((2,4-Dimethoxybenzyl)oxy)isoindoline-1,3-dione；2-[(2,4-dimethoxyphenyl)methoxy]isoindole-1,3-dione
• CAS: 216067-79-7
• 化学式: C₁₇H₁₅NO₅
• 分子量: 313.31
• InChiKey: JRKPFWCVODWKST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(2,4-Dimethoxyphenyl)methyl]phthalimide 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 甲基肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 2-amino-N-(2,4-dimethoxybenzyloxy)-3-hydroxypropionamide
  参考文献：
  名称：

  High-Throughput Catch-and-Release Synthesis of Oxazoline Hydroxamates. Structure−Activity Relationships in Novel Inhibitors of Escherichia coli LpxC:  In Vitro Enzyme Inhibition and Antibacterial Properties

  摘要：

  LpxC is a zinc amidase that catalyses the second step of lipid A biosynthesis in Gram-negative bacteria. Oxazolines incorporating a hydroxamic acid, which is believed to coordinate to the single essential zinc ion, at the 4-position are known inhibitors of this enzyme. Some of these enzyme inhibitors exhibit antibacterial activity through their inhibition of LpxC. We recently developed a method for the synthesis of oxazolines using resin capture and ring-forming release that eliminates traditional purification steps and can be used in high-throughput synthesis. Using our method, oxazoline hydroxamates with diverse 2-substituents were prepared in library form as candidate inhibitors for LpxC. Two conventional methods for oxazoline synthesis were also applied to generate more than 70 compounds. The groups at the 2-position included a wide variety of substituted aromatic rings and a limited selection of alkyl groups. These compounds were screened against wild-type and LpxC inhibitor-sensitive strains of Escherichia coli, as well as wildtype Pseudomonas aeruginosa. Inhibition of the E coli LpxC enzyme was also investigated. A broad correlation between enzyme inhibitory and antibacterial activity was observed, and novel compounds were discovered that exhibit antibacterial activity but fall outside earlier-known structural classes.

  DOI：

  10.1021/ja0209114
• 作为产物：
  描述：

  N-羟基邻苯二甲酰亚胺 、 2,4-二甲氧基苄醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 氯仿 为溶剂， 以82%的产率得到N-[(2,4-Dimethoxyphenyl)methyl]phthalimide
  参考文献：
  名称：

  用于合成异羟肟酸的新型羟胺

  摘要：

  已经制备了O-2，4-二甲氧基苄基羟胺和O-2，4-二甲氧基苄基-N-2,4,6-三甲氧基苄基羟胺，并将其用于制备基于生物学的基于异羟肟酸的抑制剂。

  DOI：

  10.1016/s0040-4039(98)01760-2

文献信息

• New hydroxylamines for the synthesis of hydroxamic acids
  作者：Bernard Barlaam、Annie Hamon、Mickaël Maudet

  DOI：10.1016/s0040-4039(98)01760-2

  日期：1998.10

  O-2,4-Dimethoxybenzyl hydroxylamine and O-2,4-dimethoxybenzyl-N-2,4,6-trimethoxybenzyl hydroxylamine have been prepared and used for the preparation of hydroxamic acid based inhibitors of biological interest.

  已经制备了O-2，4-二甲氧基苄基羟胺和O-2，4-二甲氧基苄基-N-2,4,6-三甲氧基苄基羟胺，并将其用于制备基于生物学的基于异羟肟酸的抑制剂。
• <i>O</i>-Protected <b><i>N</i></b>-(2-Nitrophenylsulfonyl)hydroxylamines: Novel Reagents for the Synthesis of Hydroxamates
  作者：Urszula Slomczynska、Poreddy Reddy、Otto Schall、James Wheatley、Leonard Rosik、Joseph McClurg、Garland Marshall

  DOI：10.1055/s-2001-14567

  日期：——

  Preparative methods for novel O-protected N-(2-nitrophenylsulfonyl)hydroxylamines (8a-e) are described. Their versatility as intermediates en route to polyhydroxamates is exemplified by the synthesis of a non-amide DFO analog 22.

  本文描述了新型O保护N-(2-硝基苯磺酰)羟胺（8a-e）的制备方法。它们作为多羟肟酸中间体的多功能性通过合成一种非酰胺的DFO类似物22得到了体现。
• Design, synthesis and molecular modeling study of iminodiacetyl monohydroxamic acid derivatives as MMP inhibitors
  作者：M. Amélia Santos、Sérgio M. Marques、Tiziano Tuccinardi、Paolo Carelli、Laura Panelli、Armando Rossello

  DOI：10.1016/j.bmc.2006.07.011

  日期：2006.11

  As the matrix metalloproteinases (MMPs) can be massively up-regulated in degenerative tissues and degrade the extracellular matrix, these key enzymes are promising targets for the therapy of cancer and other degenerative diseases. Here, we are presenting a series of new non-peptidic hydroxamate-based matrix metalloproteinase inhibitors, MMPIs, incorporating the iminodiacetic (IDA) hydroxamic acid scaffold, as mimics of truncated peptidic MMPIs. A series of alkylaryl and sulfonylaryl groups, on the IDA basic scaffold, was investigated with the aim of improving potency and selectivity against MMPs involved in degenerative diseases. The sulfonamide based IDA derivatives studied (compounds B1-B3) showed to be potent (nM range) against deep S1' pocket MMPs enzymes (i.e., MMP-2). (c) 2006 Elsevier Ltd. All rights reserved.
• US7598242B2
  申请人：——

  公开号：US7598242B2

  公开（公告）日：2009-10-06
• [EN] COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] COMPOSES DESTINES AU TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：SCHERING CORP

  公开号：WO2003053915A2

  公开（公告）日：2003-07-03

  This invention relates to compounds of the Formula (I):(Chemical formula should be inserted here as it appears on abstract in paper form)(I)or a pharmaceutically acceptable salt, solvate or isomer thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, TNF-alpha or combinations thereof.