(Z)-1-偶氮基-3-(4-硝基苯氧基)-3-氧代丙-1-烯-2-醇 | 111337-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: (Z)-1-偶氮基-3-(4-硝基苯氧基)-3-氧代丙-1-烯-2-醇
• 中文别名: 4-硝基苯基3-重氮基丙酮酸酯
• 英文名称: p-nitrophenyl 3-diazopyruvate
• 英文别名: (4-nitrophenyl) (3Z)-3-diazo-2-oxopropanoate
• CAS: 111337-51-0
• 化学式: C₉H₅N₃O₅
• 分子量: 235.156
• InChiKey: VCRPKWLNHWPCSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  间苯二胺 、 (Z)-1-偶氮基-3-(4-硝基苯氧基)-3-氧代丙-1-烯-2-醇 以 乙酸乙酯 为溶剂， 反应 12.0h， 以83%的产率得到N-(3-aminophenyl)-3-diazopyruvamide
  参考文献：
  名称：

  Development of a New Family of Thiol Specific Photoactivatable Crosslinking Agents

  摘要：

  A new family of thiol specific photoactivatable cross-linking agents has been developed by the combination of the bromoacetyl function and the diazopyruvamide group. Various bromoacetyl-diazopyruvoyl (bromoacetyl-DAP) derivatives have been synthesized and their reaction chemistry with thiols investigated and photochemistry explored. The trimodular bioprobe 17 design evolved from application of this chemistry. The trifunctionality of 17 is characterized by the presence of (1) a bromoacetyl function that modifies thiol groups through alkylation, (2) a diazopyruvoyl function which upon photolysis undergoes Wolff rearrangement generating a reactive ketene that can acylate nucleophiles, and (3) a phenolic function that acts as a characterization handle through radioiodination labeling via standard techniques. These bifunctional and trifunctional photoprobes typified by N-bromoacetyl-N'-(3-diazopyruvoyl)-m-phenylenediamine (7a) have been used to successfully cross-link a 14 aa peptide(Q) from the alpha(2)-adrenergic receptor to purified G protein.

  DOI：

  10.1021/jo00126a055
• 作为产物：
  描述：

  重氮甲烷 、 氯氧代乙酸 4-硝基苯基酯 以 乙醚 为溶剂， 以50%的产率得到(Z)-1-偶氮基-3-(4-硝基苯氧基)-3-氧代丙-1-烯-2-醇
  参考文献：
  名称：

  Photoactivated Coumaryl-diazopyruvate Fluorescent Label for Amine Functional Groups of Tissues Containing Type-I Collagen¶

  摘要：

  The design, synthesis and application of a new fluorescent-labeling reagent for collagen has been developed as a prerequisite for the design of a photoactivated collagen-crosslinking compound for surgical wound closure. The amine groups in collagen are the targets of a rational design for a new fluorophore because natural collagen crosslinks are formed between primary (1) amine groups of lysine and hydroxylysine. The availability of 1degrees amines for crosslinking in native collagenous tissues was evaluated by reacting tendon and corneal samples with o-phthalaldehyde and dansyl chloride, fluorophores commonly used for the detection of 1 and 2 amines. The resulting fluorescent collagen fibrils indicated the presence of amines in native tissue. Subsequently, a photoactivated fluorescent label for 1 and 2 amines, coumaryl gamma-amino-butyric acid diazopyruvate (CGDP), was designed and synthesized. CGDP was first used to photolabel poly-L-lysine, forming a fluorescent, covalent bond to the 1 amine. CGDP was then photoreacted with corneal and tendon tissue samples to produce CGDP fluorescent-labeled samples that were statistically significantly more fluorescent than were the controls. These experiments support the postulate that 1 or 2 (or both) amines in native collagenous tissues are available to serve as targets for photoactivated collagen crosslinkers for wound closure.

  DOI：

  10.1562/0031-8655(2002)076<0473:pcdflf>2.0.co;2

文献信息

• [EN] COMPOUNDS, DEVICES, AND USES THEREOF<br/>[FR] COMPOSÉS, DISPOSITIFS ET UTILISATIONS ASSOCIÉES
  申请人：SIGILON THERAPEUTICS INC

  公开号：WO2018067615A1

  公开（公告）日：2018-04-12

  The present invention provides compounds, e.g., compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are implantable elements (e.g., devices and materials) comprising the same, as well as methods of use thereof, e.g., for treating or preventing a disease, disorder, or condition.

  本发明提供化合物，例如，具有式（I）的化合物和药用可接受的盐、溶剂化合物、水合物、互变异构体、立体异构体、同位素标记衍生物及其组合物。还提供包括相同化合物的可植入元件（例如，设备和材料），以及使用方法，例如，用于治疗或预防疾病、紊乱或状况。
• [EN] FUNCTIONALIZED LINEAR LIGANDS AND COMPLEXES THEREOF<br/>[FR] LIGANDS LINÉAIRES FONCTIONNALISÉS ET COMPLEXES DE CEUX-CI
  申请人：LUMIPHORE INC

  公开号：WO2016106241A1

  公开（公告）日：2016-06-30

  The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

  这项发明涉及可用于治疗和诊断应用的化合物和配合物。
• [EN] BORONATE-MEDIATED DELIVERY OF MOLECULES INTO CELLS<br/>[FR] ADMINISTRATION DE MÉDICAMENT MÉDIÉE PAR LES BORONATE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2013110005A1

  公开（公告）日：2013-07-25

  Methods for enhancing cellular uptake of cargo molecules by boronating the cargo molecule, particularly with one or more phenylboronic acid groups. Cellular uptake includes at least partial uptake into the cytosol. Boronation includes ligating, crosslinking or otherwise bonding one or more phenylboronic acids substituted to contain a reactive group to a cargo molecule. Boronation also includes ligating, crosslinking or otherwise bonding a phenylboronated oligopeptide to a cargo molecule. The phenylboronate groups are optionally conjugated to the cargo molecule via linking moieties that can be selectively cleaved. The invention includes certain phenylboronates which are boronation reagents, certain boronated oligopeptides and certain boronated peptides and proteins. The invention also includes kits for enhancing cellular uptake of cargo molecules by boronation with one or more phenylboronates or boronated oligopeptides.

  增强货物分子细胞摄取的方法，通过将货物分子硼酸化，特别是与一个或多个苯硼酸基团硼酸化。细胞摄取至少包括部分摄取到细胞质中。硼酸化包括将一个或多个含有反应基团的取代苯硼酸与货物分子连接、交联或以其他方式键合。硼酸化还包括将苯硼酸化的寡肽与货物分子连接、交联或以其他方式键合。可选地，苯硼酸基团通过可以选择性切割的连接基团与货物分子连接。本发明包括某些作为硼酸化试剂的苯硼酸、某些硼酸化的寡肽以及某些硼酸化的肽和蛋白质。本发明还包括通过用一种或多种苯硼酸或硼酸化寡肽硼酸化来增强货物分子细胞摄取的试剂盒。
• Interferon beta: remodeling and glycoconjugation of interferon beta
  申请人：Neose Technologies, Inc.

  公开号：US20040115168A1

  公开（公告）日：2004-06-17

  The invention includes methods and compositions for remodeling a peptide molecule, including the addition or deletion of one or more glycosyl groups to a peptide, and/or the addition of a modifying group to a peptide.

  本发明包括重塑肽分子的方法和组合物，包括向肽添加或删除一个或多个糖基团，和/或向肽添加修饰基团。
• Glycoconjugation methods and proteins/peptides produced by the methods
  申请人：Neose Technologies, Inc.

  公开号：US20040142856A1

  公开（公告）日：2004-07-22

  The invention includes methods and compositions for remodeling a peptide molecule, including the addition or deletion of one or more glycosyl groups to a peptide, and/or the addition of a modifying group to a peptide.

  本发明包括重塑肽分子的方法和组合物，包括向肽添加或删除一个或多个糖基团，和/或向肽添加修饰基团。