4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbonate | 415918-01-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbonate
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-nitrophenoxy)carbonyloxyoxan-2-yl]methyl acetate
• CAS: 415918-01-3
• 化学式: C₂₁H₂₃NO₁₄
• 分子量: 513.412
• InChiKey: VDNXOZJJIOFMSJ-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  196
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbonate 在 四氯苯醌 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成
  参考文献：
  名称：

  用于同时检测多种酶活性的多色可激活拉曼探针

  摘要：

  基于炔烃或腈标签的拉曼探针有望用于高度多重成像。然而，用拉曼探针检测酶活性很困难，因为很少有机制可用于调节振动响应。在这里，我们提出了一种制备可激活拉曼探针的一般策略，该探针在生理条件下与酶反应时，由于电子预共振 (EPR) 显示增强的拉曼信号。我们鉴定了一种在 9 位带有腈基的呫吨衍生物 (9CN-JCP) 作为合适的支架染料，并合成了四种可激活的拉曼探针，它们针对不同的酶（三种氨肽酶和一种糖苷酶）并调整到不同的振动通过腈基的同位素编辑频率。我们验证了目标酶对这些探针的拉曼信号的激活，并成功地同时对活细胞中的四种酶活性进行了成像。不同的细胞系显示出这些酶活性的不同模式。

  DOI：

  10.1021/jacs.0c09200
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三乙胺 、 苄胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-nitrophenyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbonate
  参考文献：
  名称：

  New Glycosidase Activated Nitric Oxide Donors:  Glycose and 3-Morphorlinosydnonimine Conjugates

  摘要：

  To achieve site specific delivery of nitric oxide (NO), a new class of glycosidase activated NO donors has been developed. Glucose, galactose, and N-acetylneuraminic acid were covalently coupled to 3-morphorlinosydnonimine (SIN-1), a mesoionic heterocyclic NO donor, via a carbamate linkage at the anomeric position. The beta-glycosides were successfully prepared for these conjugates, while the alpha-glycosidic compounds were very unstable. The new stable sugar-NO conjugates could release NO in the presence of glycosidases. Such NO prodrugs may be used as enzyme activated NO donors in biomedical research.

  DOI：

  10.1021/jo050010o

文献信息

• Synthesis and biological analysis of novel glycoside derivatives of l-AEP, as targeted antibacterial agents
  作者：Richard Bovill、Philip G. Evans、Gemma L. Howse、Helen M.I. Osborn

  DOI：10.1016/j.bmcl.2016.05.052

  日期：2016.8

  feasibility of using glycoside derivatives of the antibacterial compound l-R-aminoethylphosphonic acid (l-AEP) has been investigated. These derivatives are hypothesized to be taken up by bacterial cells via carbohydrate uptake mechanisms, and then hydrolyzed in situ by bacterial borne glycosidase enzymes, to selectively afford l-AEP. Therefore the synthesis and analysis of ten glycoside derivatives of l-AEP

  为了开发用于治疗细菌感染的靶向方法，已经研究了使用抗菌化合物1 - R-氨基乙基膦酸（1- AEP）的糖苷衍生物的可行性。假设这些衍生物被细菌细胞通过碳水化合物吸收机制吸收，然后被细菌携带的糖苷酶原位水解，以选择性地产生1- AEP。因此，报道了用于选择性靶向特定细菌的十种1- AEP的糖苷衍生物的合成和分析。讨论了这些衍生物在两种不同培养基中抑制一组革兰氏阴性细菌生长的能力。β-糖苷（12a）和（12b）含有通过氨基甲酸酯键与葡萄糖或半乳糖连接的1- AEP，抑制了多种微生物的生长，其最佳MICs ＜0.75mg / ml；对于大多数物种而言，抑制作用与等效生色糖苷的水解密切相关。这表明对于（12a）和（12b），1- AEP的释放确实取决于相应糖苷酶的存在。
• [EN] ENDOSOMAL ESCAPE DOMAINS FOR DELIVERY OF MACROMOLECULES INTO CELLS<br/>[FR] DOMAINES D'ÉCHAPPEMENT ENDOSOMAL POUR INTRODUIRE DES MACROMOLÉCULES DANS DES CELLULES
  申请人：UNIV CALIFORNIA

  公开号：WO2022081589A1

  公开（公告）日：2022-04-21

  The disclosure provides for compounds and compositions comprising universal endosomal escape domains, and applications thereof, including for delivering macromolecules into cells.

  本公开提供了包含通用内体逃逸结构域的化合物和组合物，以及它们的应用，包括将大分子递送到细胞中。
• SYNTHESIS OF NEW GALACTOSYL AND LACTOSYL CARBAMATE-CONTAINING GLYCOLIPIDS
  作者：Michel Azoulay、Virginie Escriou、Jean-Claude Florent、Claude Monneret

  DOI：10.1081/car-100108661

  日期：2001.12.31

  An efficient synthesis of mono-, di- and tetrasaccharides linked to a lipid has been developed. Galactose or lactose was covalently coupled to a glycyldioctadecylamide, via well-defined chemical steps, in both an alpha and beta anomeric configuration. The multiantennary galactosyl ligands were obtained using 1,3-diamino-2-propanol as a scaffold.
• [EN] PRODRUGS WITH 1-(DISULFANYL)ALKYLOXY-CARBONYL UNITS<br/>[FR] PROMÉDICAMENTS À MOTIFS 1-(DISULFANYL)ALKYLOXY-CARBONYLE
  申请人：[en]PHARMACYTICS B.V.

  公开号：WO2022271018A1

  公开（公告）日：2022-12-29

  The invention is in the field of medical sciences. It provides new pharmaceutical methods and preparations. The invention relates to methods for improving the pharmacokinetic, physicochemical or pharmaceutical properties of drugs by converting the drug into a promoiety-containing 1-substituted disulfanylalkyl carbonate, thiocarbamate or carbamate prodrug. In particular, the invention relates to methods for improving the solubility, permeability, stability and/or oral bioavailability of a drug by converting the drug into a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate prodrug. The invention also provides new compositions comprising a drug covalently attached to a promoiety-containing 1-(disulfanylalkyl) carbonate, thiocarbonate or carbamate. More in particular, the invention relates to a method for increasing the oral bioavailability of a drug by covalently attaching a promoiety-containing 1-disulfanylalkyloxycarbonyl unit to a hydroxyl or amine containing drug in which the promoiety contains a 1-0-, 1-S-, 6-0- or 6-S-linked monosaccharide. Formula I