methyl 2-azido-4,5-dimethoxybenzoate

• 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 2-azido-4,5-dimethoxybenzoate
• 英文别名: Methyl 2-azido-4,5-dimethoxybenzoate
• 化学式: C₁₀H₁₁N₃O₄
• 分子量: 237.215
• InChiKey: DQICSZZWMMDVJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-4,5-dimethoxybenzoate 在 四丁基氯化铵 、 sodium methylate 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 0.83h， 生成 5-chloro-7,8-dimethoxy-3-(phenylsulfonyl)-[1,2,3]triazolo[1,5-a]quinazoline
  参考文献：
  名称：

  [EN] METHODS AND COMPOUNDS FOR ANTIMICROBIAL INTERVENTION
  [FR] PROCÉDÉS ET COMPOSÉS POUR INTERVENTION ANTIMICROBIENNE

  摘要：

  公开号：

  WO2009151561A3
• 作为产物：
  描述：

  2-氨基-4,5-二甲氧基苯甲酸甲酯 在 盐酸 、 sodium nitrite 、 sodium azide 、 sodium acetate 作用下， 以 水 为溶剂， 反应 0.25h， 以82%的产率得到methyl 2-azido-4,5-dimethoxybenzoate
  参考文献：
  名称：

  Development of improved inhibitors of wall teichoic acid biosynthesis with potent activity against Staphylococcus aureus

  摘要：

  A small molecule (1835F03) that inhibits Staphylococcus aureus wall teichoic acid biosynthesis, a proposed antibiotic target, has been discovered. Rapid, parallel, solution-phase synthesis was employed to generate a focused library of analogs, providing detailed information about structure-activity relationships and leading to the identification of targocil, a potent antibiotic. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.036

文献信息

• Simple and facile reduction of azides to amines: synthesis of DNA interactive pyrrolo[2,1- c ][1,4]benzodiazepines
  作者：Ahmed Kamal、P.S.M.M. Reddy、D.Rajasekhar Reddy

  DOI：10.1016/s0040-4039(02)01453-3

  日期：2002.9

  with hydriodic acid has been investigated and found to result in high yields. This reductive methodology which proceeds under non refluxing condition has been extended for the synthesis of DNA-interactive pyrrolo[2,1-c][1,4] benzodiazepine antibiotics.

  已经研究了用氢碘酸将芳香族叠氮化合物还原为相应的胺，发现其收率很高。这种在非回流条件下进行的还原性方法已扩展为合成DNA相互作用的吡咯并[2,1- c ] [1,4]苯二氮卓类抗生素。
• An Efficient Selective Reduction of Aromatic Azides to Amines Employing BF₃·OEt₂/NaI: Synthesis of Pyrrolobenzodiazepines
  作者：Ahmed Kamal、Ch. Reddy、N. Shankaraiah、N. Markandeya

  DOI：10.1055/s-2008-1072742

  日期：2008.5

  A selective and facile method for the reduction of aromatic azides to amines by employing borontrifluoride diethyl etherate and sodium iodide. This methodology has been applied towards the preparation of biologically important imine-containing pyrrolobenzodiazepines and their dilactams through intramolecular reductive-cyclization process. In this protocol the reagent systems are amenable for the generation

  使用三氟化硼乙醚合物和碘化钠将芳族叠氮化物还原为胺的选择性和简便方法。该方法已应用于通过分子内还原环化过程制备具有生物学意义的含亚胺的吡咯并苯二氮卓类及其双内酰胺。在该协议中，试剂系统适用于生成溶液相组合合成。
• METHODS AND COMPOUNDS FOR ANTIMICROBIAL INTERVENTION
  申请人：Kahne Suzanne Walker

  公开号：US20120046282A1

  公开（公告）日：2012-02-23

  The present invention provides Wall Teichoic Acid biosynthesis inhibitors such as compound 1835F03 (targocil) and related synthetic analogs. The invention also provides pharmaceutical compositions thereof and methods for treating bacterial infection and the suppression of growth of bacterial cells by administering a Wall Teichoic Acid biosynthesis inhibitor. The invention is particularly useful for the treatment of Methicillin-resistant Staphylococcus aureus (MRSA). The invention further provides procedures for the syntheses of Wall Teichoic Acid biosynthesis inhibitors. The invention also provides methods for the identification of antibacterial therapeutic agents.

  本发明提供了壁垂体酸生物合成抑制剂，例如化合物1835F03（targocil）和相关合成类似物。本发明还提供了其制药组合物和通过给予壁垂体酸生物合成抑制剂治疗细菌感染和抑制细菌细胞生长的方法。本发明特别适用于治疗甲氧西林耐药金黄色葡萄球菌（MRSA）感染。本发明还提供了壁垂体酸生物合成抑制剂的合成方法。本发明还提供了抗菌治疗剂的鉴定方法。
• Methods and compounds for antimicrobial intervention
  申请人：Kahne Suzanne Walker

  公开号：US08598342B2

  公开（公告）日：2013-12-03

  The present invention provides Wall Teichoic Acid biosynthesis inhibitors such as compound 1835F03 (targocil) and related synthetic analogs. The invention also provides pharmaceutical compositions thereof and methods for treating bacterial infection and the suppression of growth of bacterial cells by administering a Wall Teichoic Acid biosynthesis inhibitor. The invention is particularly useful for the treatment of Methicillin-resistant Staphylococcus aureus (MRSA). The invention further provides procedures for the syntheses of Wall Teichoic Acid biosynthesis inhibitors. The invention also provides methods for the identification of antibacterial therapeutic agents.

  本发明提供了壁葡聚糖生物合成抑制剂，例如化合物1835F03（targocil）及其相关的合成类似物。本发明还提供了其制药组合物和通过给予壁葡聚糖生物合成抑制剂治疗细菌感染和抑制细菌细胞生长的方法。本发明特别适用于治疗甲氧西林耐药金黄色葡萄球菌（MRSA）。本发明还提供了壁葡聚糖生物合成抑制剂的合成方法。本发明还提供了抗细菌治疗剂的鉴定方法。
• Annulation-Triggered Denitrogenative Transformations of 2-(5-Iodo-1,2,3-triazolyl)benzoic Acids
  作者：Vladislav A. Voloshkin、Yury N. Kotovshchikov、Gennadij V. Latyshev、Nikolay V. Lukashev、Irina P. Beletskaya

  DOI：10.1021/acs.joc.2c00235

  日期：2022.6.3

  ability of [1,2,3]triazolobenzoxazinones to act as a source of “hidden” diazo group was discovered. These diazo precursors can be easily prepared by the intramolecular cyclization of 2-(5-iodo-1,2,3-triazolyl)benzoic acids. The Cu-catalyzed capture of the hidden diazo group allows for further functionalization through the denitrogenative pathway. The transformations proceed via the formation of either

  发现了 [1,2,3] 三唑并苯并恶嗪酮作为“隐藏”重氮基团来源的能力。这些重氮前体可以很容易地通过 2-(5-iodo-1,2,3-triazolyl) 苯甲酸的分子内环化来制备。隐藏的重氮基团的 Cu 催化捕获允许通过脱氮途径进行进一步的功能化。转化通过形成重氮亚胺或重氮酰胺中间体进行。使用一锅环化/重氮捕获程序开发了各种邻氨基苯甲酰胺以及硫醇化苯并恶嗪酮的新途径。