methyl 5-azidolevulinate | 159150-70-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 5-azidolevulinate
• 英文别名: methyl 5-azido-4-oxopentanoate；Pentanoic acid, 5-azido-4-oxo-, methyl ester
• CAS: 159150-70-6
• 化学式: C₆H₉N₃O₃
• 分子量: 171.156
• InChiKey: YXCSXSQIHFZDPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-azidolevulinate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、400.01 kPa 条件下， 反应 6.0h， 生成 methyl 3-(2-mercapto-4-imidazolyl)propionate
  参考文献：
  名称：

  Thiazole- and imidazole-containing peptidomimetic inhibitors of protein farnesyltransferase

  摘要：

  Mimetics of the C-terminal CAAX tetrapeptide of Ras protein were designed replacing internal dipeptide AA with 4-amino-2-phenylbenzoic acid and cysteine (C) with 2-amino-4-thiazolyl-, 2-mercapto-4-thiazolyl-, 2-mercapto-4-imidazolyl- and 2-methylmercapto-4-thiazolyl-acetic or propionic acid. The compound in which C is replaced by 2-amino-4-thiazolylacetic acid inhibited FTase activity in the low nanomolar range and showed antiproliferative effect on rat aortic smooth muscle cells interfering with Ras farnesylation. On the basis of these results, 2-aminothiazole can be considered as an alternative to heterocycles, such as pyridine and imidazole, normally used in FTase inhibitors designed as non-thiol CAAX mimetics. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.003
• 作为产物：
  描述：

  1,2,4-三乙氧基苯 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以100%的产率得到methyl 5-azidolevulinate
  参考文献：
  名称：

  酮的选择性溴化。5-氨基乙酰丙酸的简便合成

  摘要：

  摘要 不对称酮与 Br2 在甲醇中的溴化反应在较少取代的甲基碳上以良好的产率区域选择性地进行。使用这种方法溴化乙酰丙酸，然后进行叠氮化和胺化，以 36% 的总产率高效地三步合成 5-氨基乙酰丙酸。

  DOI：

  10.1080/00397919408010567

文献信息

• A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry
  作者：Chrysie Aggelidou、Theodossis A Theodossiou、Antonio Ricardo Gonçalves、Mariza Lampropoulou、Konstantina Yannakopoulou

  DOI：10.3762/bjoc.10.251

  日期：——

  delta-aminolevulinic acid (1) moieties on the narrow periphery of a beta-cyclodextrin (beta-CD) derivative through hydrolysable bonds was implemented, in order to generate a water-soluble, molecular/drug carrier with the capacity to undergo intracellular transformation into protoporphyrin IX (PpIX), an endogenous powerful photosensitizer for photodynamic therapy (PDT). The water-soluble derivative 2 was prepared by

  通过产生可水解键，在β-环糊精（β-CD）衍生物的狭窄边缘上接枝了δ-氨基乙酰丙酸（1）部分，以生成具有分子内渗透能力的水溶性分子/药物载体转化为原卟啉IX（PpIX），这是一种用于光动力疗法（PDT）的内源性强效光敏剂。通过用七（6-羟乙基氨基-6-脱氧）-β-环糊精酯化δ-叠氮乙酰丙酸酯酸来制备水溶性衍生物2，其平均取代度DS = 3。共聚焦显微镜观察到，这些细胞产生了强烈的红色荧光，这显然是由于细胞内机制参与了PpIX的形成。结合物2进一步与荧光素标记的模型客体分子复合，该分子成功地转运到细胞中，从而证明了该衍生物的双峰作用。目前的工作表明了CD在智能应用中的多功能性，并在水溶性和缺乏聚集方面构成了我们先前显示的PpIX-β-CD共轭的进步。
• Synthesis of Novel and Stable 5-Aminolevulinic Acid Derivatives for the Efficient Synthesis of 5-Aminolevulinic Acid Based Prodrugs
  作者：Reinhard Neier、Ramakrishnan Vallinayagam、Hugo Bertschy、Yann Berger、Virginie Wenger

  DOI：10.1055/s-2007-990825

  日期：2007.12

  The efficient synthesis of two stable, easily handled precursors of 5-aminolevulinate is reported. These precursors are stable to the chemical transformation needed for the synthesis of bioconjugates and can be readily deprotected in good yields.

  报告了两种稳定、易于处理的5-氨基己酸前体的高效合成。这些前体对合成生物偶联物所需的化学转化稳定，并且可以在良好的产率下方便地去保护。
• The Synthesis of a Pyrazol Analogon of Porphobilinogen with the Help of the Mukaiyama Aldol Reaction
  作者：André Chaperon、Hugo Bertschy、Anne-Laurence Franz-Schrumpf、Bertrand Hugelet、Antonia Neels、Helen Stoeckli-Evans、Reinhard Neier

  DOI：10.2533/000942903777678812

  日期：——

  The synthesis of a pyrazol analogon of porphobilinogen is described. The Mukaiyama crossed aldol reaction is the key step of our approach. The retrosynthetic analysis follows the mechanism for the biosynthesis of porphobilinogen initially proposed by Shemin.

  描述了吡唑类似物porphobilinogen的合成。Mukaiyama交叉醛缩反应是我们方法的关键步骤。逆合成分析遵循了最初由Shemin提出的porphobilinogen生物合成机制。
• 5-azido-laevulinic acid, method for the production thereof and its use
  申请人：Aldenkortt Sven

  公开号：US20060086443A1

  公开（公告）日：2006-04-27

  The present invention relates to 5-azido levulinic acid, a process for its preparation, its use. Using 5-azido levulinic acid as starting material for the synthesis of 5-amino levulinic acid hydrochloride it is possible to obtain the latter in good yield an in pharmaceutical acceptable quality. 5-Azido levuliniv acid is synthesized in that methyl 5-bromo levulinate and/or methyl 5-chloro levulinate is converted with aqueous hydrochloric acid and as a result of an incomplete bromine/chlorine exchange at the C-5-postion a mixture of 5-chloro levulinic acid and 5-bromo levulinic acid is obtained, and the obtained 5-chloro levulinic acid, a mixture of 5-chloro levulinic acid and 5-bromo levulinic acid and the pure 5-bromo levulinic acid is transferred into 5-azido levulinic acid by conversion with a nucleophilic azide.

  本发明涉及5-偶氮基左旋酸、其制备过程及其用途。使用5-偶氮基左旋酸作为合成5-氨基左旋酸盐酸盐的起始物质，可以在良好的收率和药用可接受的质量下获得后者。通过用水合盐酸转化甲基5-溴左旋酸酯和/或甲基5-氯左旋酸酯，由于C-5位置的不完全溴/氯交换，得到一种5-氯左旋酸和5-溴左旋酸的混合物，然后将所得的5-氯左旋酸、5-氯左旋酸和5-溴左旋酸的混合物以及纯的5-溴左旋酸通过亲核偶氮化合成为5-偶氮基左旋酸。
• Method for obtaining 5-halogenolaevulinic acid alkyl esters
  申请人：Aldenkortt Dr Sven

  公开号：US20050070727A1

  公开（公告）日：2005-03-31

  A method for obtaining a 5-bromolevulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester from either a bromination mixture or a chlorination mixture, containing either a 5-bromo-levulinic acid methyl ester or a 5-chlorolevulinic acid methyl ester, respectively, produced by either brominating or chlorinating levulinic acid or a levulinic acid methyl ester, and further including the steps of dissolving the bromination or chlorination mixture in an organic solvent or solvent mixture and cooling the solution, preferably to −20° C.-−40° C., with the 5-bromolevulinic acid methyl ester or 5-chlorolaevulinic acid methyl ester being crystallized out of the solution. The 5-bromolevulinic acid methyl ester or 5-chlorolevulinic acid is then isolated by draining off the solution with the remaining bromination mixture or chlorination mixture, as appropriate.

  从溴化混合物或氯化混合物中获取5-溴丙酮酸甲酯或5-氯丙酮酸甲酯的方法，分别包含5-溴丙酮酸甲酯或5-氯丙酮酸甲酯，这些物质是通过溴化或氯化丙酮酸或丙酮酸甲酯产生的。进一步包括将溴化或氯化混合物溶解在有机溶剂或溶剂混合物中，并冷却溶液，最好冷却至-20°C至-40°C，其中5-溴丙酮酸甲酯或5-氯丙酮酸甲酯从溶液中结晶出来。然后通过排出剩余的溴化混合物或氯化混合物，分离出5-溴丙酮酸甲酯或5-氯丙酮酸甲酯。