methyl 3,4-dibromobenzoate | 51329-16-9

• 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: methyl 3,4-dibromobenzoate
• 英文别名: 3,4-dibromobenzoic acid methyl ester；Methyl-3,4-dibromobenzoat
• CAS: 51329-16-9
• 化学式: C₈H₆Br₂O₂
• 分子量: 293.942
• InChiKey: PVBRMXRXKPVNRU-UHFFFAOYSA-N

物化性质

• 熔点：
  61-64 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  318.5±22.0 °C(Predicted)
• 密度：
  1.840±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3,4-dibromobenzoate 在 lithium aluminium tetrahydride 、 三乙胺 、 sodium iodide 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丁酮 为溶剂， 反应 19.5h， 生成 3,4-dibromophenylacetonitrile
  参考文献：
  名称：

  Discovery of Potent and Selective SH2 Inhibitors of the Tyrosine Kinase ZAP-70

  摘要：

  A series of 1,2,4-oxadiazole analogues has been shown to be potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70, a potential therapeutic target for immune suppression. These compounds typically are 200-400-fold more potent than the native, monophosphorylated tetrapeptide sequences. When compared with the high-affinity xi-1-ITAM peptide (Ac-NQL-pYNELNLGRREE-pYDVLD-NH2, wherein pY refers to phosphotyrosine) some of the best 1,2,4-oxadiazole analogues are approximately 1 order of magnitude less active. This series of compounds displays an unprecedented level of selectivity over the closely related tyrosine kinase Syk, as well as other SH2-containing proteins such as Src and Grb2. Gel shift studies using a protein construct consisting only of C-terminal ZAP-70 SH2 demonstrate that these compounds can effectively engage this particular SH2 domain.

  DOI：

  10.1021/jm990229t
• 作为产物：
  描述：

  对溴苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 反应 15.0h， 生成 methyl 3,4-dibromobenzoate
  参考文献：
  名称：

  Discovery of Potent and Selective SH2 Inhibitors of the Tyrosine Kinase ZAP-70

  摘要：

  A series of 1,2,4-oxadiazole analogues has been shown to be potent and selective SH2 inhibitors of the tyrosine kinase ZAP-70, a potential therapeutic target for immune suppression. These compounds typically are 200-400-fold more potent than the native, monophosphorylated tetrapeptide sequences. When compared with the high-affinity xi-1-ITAM peptide (Ac-NQL-pYNELNLGRREE-pYDVLD-NH2, wherein pY refers to phosphotyrosine) some of the best 1,2,4-oxadiazole analogues are approximately 1 order of magnitude less active. This series of compounds displays an unprecedented level of selectivity over the closely related tyrosine kinase Syk, as well as other SH2-containing proteins such as Src and Grb2. Gel shift studies using a protein construct consisting only of C-terminal ZAP-70 SH2 demonstrate that these compounds can effectively engage this particular SH2 domain.

  DOI：

  10.1021/jm990229t

文献信息

• SAR Studies on Aromatic Acylhydrazone-Based Inhibitors of Fungal Sphingolipid Synthesis as Next-Generation Antifungal Agents
  作者：Krupanandan Haranahalli、Cristina Lazzarini、Yi Sun、Julia Zambito、Senuri Pathiranage、J. Brian McCarthy、John Mallamo、Maurizio Del Poeta、Iwao Ojima

  DOI：10.1021/acs.jmedchem.9b01004

  日期：2019.9.12

  Recently, the fungal sphingolipid glucosylceramide (GlcCer) synthesis has emerged as a highly promising new target for drug discovery of next-generation antifungal agents, and we found two aromatic acylhydrazones as effective inhibitors of GlcCer synthesis based on HTP screening. In the present work, we have designed libraries of new aromatic acylhydrazones, evaluated their antifungal activities (MIC80

  最近，真菌鞘脂糖基神经酰胺（GlcCer）的合成已成为下一代抗真菌药的药物开发的高度有希望的新目标，我们基于HTP筛选发现了两种芳香族酰基hydr作为GlcCer合成的有效抑制剂。在目前的工作中，我们设计了新的芳香族酰基hydr的文库，评估了它们对新孢子虫的抗真菌活性（MIC80和时间杀灭谱），并进行了广泛的SAR研究，从而鉴定了五种有前途的先导化合物，极高的选择性指数，具有出色的杀真菌活性。此外，两种化合物对其他六种临床相关真菌菌株均具有广谱抗真菌活性。研究了这五种先导化合物与五种临床药物对七种真菌菌株的协同作用/协同作用，并获得了令人鼓舞的结果。例如，所有五个先导化合物与伏立康唑的组合对所有七个真菌菌株均表现出协同作用或加和作用。
• One Step of Palladium Catalyzed Benzodioxane Ring C–O Bond Formation, Synthesis of Isoamericanol A and Isoamericanin A
  作者：Xiaobi Jing、Yaocheng Shi、Yonghong Liu、Ying Han、Chaoguo Yan、Li Wang

  DOI：10.1081/scc-120030759

  日期：2004.12.31

  Abstract A number of benzodioxane compounds were synthesized using the palladium‐catalyzed etherification of aryl halides by employing triphenylphosphane ligands. This method was used as key step in the synthesis of two natural products isoamericanol A and isoamericanin A.

  摘要 使用三苯基膦配体，通过钯催化的芳基卤化物醚化合成了许多苯二恶烷化合物。该方法被用作合成两种天然产物异美洲醇 A 和异美洲素 A 的关键步骤。
• A convergence of photo-bergman cyclization and intramolecular chain collapse towards polymeric nanoparticles
  作者：Benchuan Zhu、Guannan Qian、Yuli Xiao、Sheng Deng、Meng Wang、Aiguo Hu

  DOI：10.1002/pola.25013

  日期：2011.12.15

  UV‐irradiation with a concurrent Bergman cyclization, resulting in well‐defined ultrafine polymeric nanoparticles. Results from NMR, Raman scattering, photoluminescence and UV‐vis spectra corroborated the presence of conjugative structures in the polymeric nanoparticles, indicating the occurrence of photo‐induced Bergman cyclization. A series of other acrylate‐based nanoparticles were investigated to confirm the

  利用烯二炔作为交联前体，将一种新颖而有效的策略（即光触发的伯格曼环化）与分子内链塌陷结合在一起，以制得尺寸小于20 nm的聚合物纳米颗粒。Enediyne图案经过精心设计，具有很高的光反应性，双键锁定在苯甲酸甲酯环中，而三键则被苯基取代。进行单电子转移活性自由基聚合，以提供分子量受控且窄分散性的线性丙烯酸酯共聚物。保利（butylarylate-合作- 5）进行了紫外线照射，并发了Bergman环化反应，得到了定义明确的超细聚合物纳米颗粒。NMR，拉曼散射，光致发光和紫外可见光谱的结果证实了聚合物纳米颗粒中共轭结构的存在，表明发生了光诱导的伯格曼环化反应。对其他一系列基于丙烯酸酯的纳米颗粒进行了研究，以确认这种独特策略在热敏但对紫外线稳定的聚合物结构中的适用性，从而使光-伯格曼环化成为制备聚合物纳米颗粒的有希望的工具。©2011 Wiley Periodicals，Inc. J Polym
• 2-Iminoisoindolinone derivatives as thrombin receptor antagonists
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2385039A1

  公开（公告）日：2011-11-09

  The present invention relates to a 2-iminopyrrolidine derivative selected from the group consisting of 1-(3-tert-butyl-4-methoxy-5-morpholino-phenyl)-2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-ethanone; 1-3-tert-butyl-5-[4-(2-hydroxy-acetyl)piperazin-1-yl]-4-methoxyphenyl}-2-(5,6-diethoxy-7-fluoro-1-imino-1,3-diyhdro-isoindol-2-yl)-ethanone; ethyl (4-3-tert-butyl-5-[2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-acetyl]-2-methoxy-phenyl}piperazin-1-yl)-acetate; 1-(3-tert-butyl-4-methoxy-5-piperazin-1-yl-phenyl)-2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-ethanone, and (4-3-tert-butyl-5-[2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-acetyl]-2-methoxy-phenyl}-piperazin-1-yl)-acetic acid; and salts thereof.

  本发明涉及选自由 1-(3-叔丁基-4-甲氧基-5-吗啉基苯基)-2-(5,6-二乙氧基-7-氟-1-亚氨基-1,3-二氢-异吲哚-2-基)-乙酮组成的组的 2-亚氨基吡咯烷衍生物；1-3-tert-butyl-5-[4-(2-hydroxy-acetyl)piperazin-1-yl]-4-methoxyphenyl}-2-(5,6-diethoxy-7-fluoro-1-imino-1,3-diyhdro-isoindol-2-yl)-ethanone;ethyl (4-3-tert-butyl-5-[2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-acetyl]-2-methoxy-phenyl}piperazin-1-yl)-acetate;1-(3-tert-butyl-4-methoxy-5-piperazin-1-yl-phenyl)-2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-ethanone, and (4-3-tert-butyl-5-[2-(5,6-diethoxy-7-fluoro-1-imino-1,3-dihydro-isoindol-2-yl)-acetyl]-2-methoxy-phenyl}-piperazin-1-yl)-acetic acid;及其盐类。
• 2-IMINOPYRROLIDINE DERIVATES
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1391451B1

  公开（公告）日：2011-11-23

表征谱图