2,5-dioxopyrrolidin-1-yl 2-hydroxy-4-nitrobenzoate | 1064652-85-2

• 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: 2,5-dioxopyrrolidin-1-yl 2-hydroxy-4-nitrobenzoate
• 英文别名: N-hydroxysuccinimidyl ester
• CAS: 1064652-85-2
• 化学式: C₁₁H₈N₂O₇
• 分子量: 280.194
• InChiKey: HEEUIOBEQDXCCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  127.05
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 2-hydroxy-4-nitrobenzoate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 3.25h， 生成 2-[(4-{[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl]amino}-2-hydroxyphenyl)formamido]pentanedioic acid
  参考文献：
  名称：

  Drugging the Folate Pathway in Mycobacterium tuberculosis: The Role of Multi-targeting Agents

  摘要：

  The folate biosynthetic pathway offers many druggable targets that have yet to be exploited in tuberculosis therapy. Herein, we have identified a series of small molecules that interrupt Mycobacterium tuberculosis (Mtb) folate metabolism by dual targeting of dihydrofolate reductase (DHFR), a key enzyme in the folate pathway, and its functional analog, Rv2671. We have also compared the antifolate activity of these compounds with that of para-aminosalicylic acid (PAS). We found that the bioactive metabolite of PAS, in addition to previously reported activity against DHFR, inhibits flavin-dependent thymidylate synthase in Mtb, suggesting a multi-targeted mechanism of action for this drug. Finally, we have shown that antifolate treatment in Mtb decreases the production of mycolic acids, most likely due to perturbation of the activated methyl cycle. We conclude that multi-targeting of the folate pathway in Mtb is associated with highly potent anti-mycobacterial activity.

  DOI：

  10.1016/j.chembiol.2019.02.013
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 4-硝基水杨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 2,5-dioxopyrrolidin-1-yl 2-hydroxy-4-nitrobenzoate
  参考文献：
  名称：

  Salicylanilides: Selective inhibitors of interleukin-12p40 production

  摘要：

  Interleukin (IL)-12p40, a subunit component of both IL-12 and IL-23, is being widely studied for its role in in. ammatory disease. As part of an effort to pro. le cellular signaling pathways across different cell types, we report salicylanilide inhibitors of IL-12p40 production in stimulated dendritic cells. Based on a hypothesis that a desirable therapeutic pro. le is one that could block IL-12p40 but not IL-6 production, we engaged in directed analoging. This resulted in salicylanilides with similar IL-12p40 related potency but enhanced selectivity relative to IL-6 production. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.07.024