N-dansyl-L-serine methyl ester | 108353-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-dansyl-L-serine methyl ester
• 英文别名: 2-N-dansyl-serine methyl ester；methyl (2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-3-hydroxypropanoate
• CAS: 108353-45-3
• 化学式: C₁₆H₂₀N₂O₅S
• 分子量: 352.411
• InChiKey: NVFROZAYLCVZKD-ZDUSSCGKSA-N

物化性质

• 熔点：
  98 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  561.9±60.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-dansyl-L-serine methyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三甲基氢氧化锡 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 217.5h， 生成 3-O-biotinyl-2-N-dansyl-serine
  参考文献：
  名称：

  Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems

  摘要：

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.089
• 作为产物：
  描述：

  丹酰氯 、 L-丝氨酸甲酯盐酸盐 在 吡啶 作用下， 反应 12.0h， 以84%的产率得到N-dansyl-L-serine methyl ester
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of Fluorescent and Photoactivatable Analogues of Antiplasmodial Naphthylisoquinolines

  摘要：

  The naphthylisoquinoline (NIQ) alkaloids from tropical Ancistrocladaceae and Dioncophyllaceae plants show high antiplasmodial activities in vitro and in vivo, even against chloroquine-resistant strains of the malaria pathogen. For the directed optimization of these activities, an investigation of the mode of action seems most rewarding. We have therefore embarked on the identification of the respective target protein in Plasmodium falciparum. For this purpose, we have developed a flexible pathway for the synthesis of a chemically divergent series of photoactive and fluorescent derivatives of such alkaloids and succeeded in preparing the first functionalized NIQ derivatives, 10, 12, and 35, suited for fluorescence and photoaffinity labeling experiments. Pharmacological investigations ensured that the modified alkaloid derivatives retained their antiplasmodial activity. The work may pave the way for a further improvement of the activity of these natural products and will thus increase their pharmacological potential as a valuable lead structure against the widespread tropical disease malaria.

  DOI：

  10.1021/jm061464w

文献信息

• DISULFIDGRUPPEN ENTHALTENDE STOFFE FÜR SELBSTORGANISIERTE TRÄGER ZUR KONTROLLIERTEN FREISETZUNG EINES WIRKSTOFFS
  申请人：Bayer Technology Services GmbH

  公开号：EP2482801A1

  公开（公告）日：2012-08-08
• [DE] DISULFIDGRUPPEN ENTHALTENDE STOFFE FÜR SELBSTORGANISIERTE TRÄGER ZUR KONTROLLIERTEN FREISETZUNG EINES WIRKSTOFFS<br/>[EN] SUBSTANCES CONTAINING DISULFIDE GROUPS FOR SELF-ASSEMBLY CARRIERS FOR CONTROLLED RELEASE OF AN ACTIVE INGREDIENT<br/>[FR] SUBSTANCES RENFERMANT DES GROUPES DISULFURE POUR VÉHICULES AUTO-ORGANISÉS PERMETTANT LA LIBÉRATION CONTRÔLÉE D'UN PRINCIPE ACTIF
  申请人：BAYER TECHNOLOGY SERVICES GMBH

  公开号：WO2011039144A1

  公开（公告）日：2011-04-07

  Die vorliegende Erfindung betrifft neuartige Stoffe zur Herstellung selbstorganisierter Wirkstoffträger in Form eines Liposoms umfassend eine Disulfidgruppe zur kontrollierten Freisetzung eines hierin enthaltenen Wirkstoffs, sowie ein Verfahren zur Freisetzung von Wirkstoffen unter Verwendung des vorgenannten Trägers.
• Synthesis and Pharmacological Evaluation of Fluorescent and Photoactivatable Analogues of Antiplasmodial Naphthylisoquinolines
  作者：Gerhard Bringmann、Christian M. Gampe、Yanina Reichert、Torsten Bruhn、Johan H. Faber、Martin Mikyna、Matthias Reichert、Matthias Leippe、Reto Brun、Christoph Gelhaus

  DOI：10.1021/jm061464w

  日期：2007.11.1

  The naphthylisoquinoline (NIQ) alkaloids from tropical Ancistrocladaceae and Dioncophyllaceae plants show high antiplasmodial activities in vitro and in vivo, even against chloroquine-resistant strains of the malaria pathogen. For the directed optimization of these activities, an investigation of the mode of action seems most rewarding. We have therefore embarked on the identification of the respective target protein in Plasmodium falciparum. For this purpose, we have developed a flexible pathway for the synthesis of a chemically divergent series of photoactive and fluorescent derivatives of such alkaloids and succeeded in preparing the first functionalized NIQ derivatives, 10, 12, and 35, suited for fluorescence and photoaffinity labeling experiments. Pharmacological investigations ensured that the modified alkaloid derivatives retained their antiplasmodial activity. The work may pave the way for a further improvement of the activity of these natural products and will thus increase their pharmacological potential as a valuable lead structure against the widespread tropical disease malaria.
• Synthesis of novel amphiphilic conjugates with a biological recognition function for developing targeted triggered liposomal delivery systems
  作者：Nicolai Brodersen、Anna Arbuzova、Andreas Herrmann、Holger Egger、Jürgen Liebscher

  DOI：10.1016/j.tet.2011.07.089

  日期：2011.10

  Several novel amphiphilic lipid derivatives were synthesized consisting of a lipid anchor connected to the hydrophilic moiety via a disulfide or glycoside bond and biotin linked to the hydrophilic part. Disulfide bonds were established by the help of 4-phenyltriazol-3,5-dione. Dansyl or fluorescein was covalently linked as fluorescent marker to some of the conjugates, allowing spectroscopic and microscopic detection. The conjugates represent first amphiphilic lipids carrying all four functions, i.e., lipophilic, hydrophilic, recognition, and disulfide cleavage group in one molecule, which are necessary for targeted, triggered drug delivery from phospholipid liposomes on demand. (C) 2011 Elsevier Ltd. All rights reserved.