(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone | 868248-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone
• 英文别名: (S)-3-(5-azidopentanoyl)-4-benzyloxazolidine-2-one；1-[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-5-azido-1-pentanone；(4S)-3-(5-azidopentanoyl)-4-benzyl-1,3-oxazolidin-2-one
• CAS: 868248-75-3
• 化学式: C₁₅H₁₈N₄O₃
• 分子量: 302.333
• InChiKey: FKCDEWFOUDODSY-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone 在 lithium hydroxide 、 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 4.5h， 生成 (2S)-5-叠氮基-2-甲基戊酸
  参考文献：
  名称：

  Synthesis of Cα methylated carboxylic acids: isosteres of arginine and lysine for use as N-terminal capping residues in polypeptides

  摘要：

  Replacement of the N-terminal alpha-amine with the isosteric methyl functionality in bioactive peptides can influence various pharmacokinetic parameters, including hydrophobicity and stability. C-alpha methylated amino acid analogues are thus of great interest to expand the repertoire of nonnatural synthons available as N-terminal 'capping' residues for peptide-based drug design. Several novel arginine and lysine analogues stereo selectively modified in the C-alpha position with a methyl group in place of the alpha-amine were prepared. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.056
• 作为产物：
  描述：

  5-溴戊酸 在 正丁基锂 、 sodium azide 、 三甲基乙酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- and C-Methylations Fine-Tune Conformation and Properties

  摘要：

  DOI：

  10.1021/acs.jmedchem.0c02036

文献信息

• Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: preparation of pyrrolizine by intramolecular capture of intermediates with alkenes or alkynes
  作者：Bao-Juan Wang、Ping Xue、Peiming Gu

  DOI：10.1039/c4cc07166b

  日期：——

  The preparation of substituted pyrrolizines through the Schmidt reaction of acyl chlorides with alkyl azides has been realized. Intramolecular capture of the isocyanate ion and N-acyliminium ion intermediates from the Schmidt process with alkene or alkyne units was achieved, and the efficiency of the conversion with respect to ring construction and bond formation was demonstrated.

  已经实现了通过酰氯与烷基叠氮化物的Schmidt反应制备取代的吡咯嗪的方法。通过Schmidt工艺使用烯烃或炔烃单元从分子内捕获异氰酸酯离子和N-酰基亚胺离子中间体，并证明了在环结构和键形成方面的转化效率。
• Conjugates of Modified Cryptophycins and RGD-Peptides Enter Target Cells by Endocytosis
  作者：Markus Nahrwold、Christine Weiß、Tobias Bogner、Felix Mertink、Jens Conradi、Benedikt Sammet、Ralf Palmisano、Soledad Royo Gracia、Thomas Preuße、Norbert Sewald

  DOI：10.1021/jm301346z

  日期：2013.3.14

  Tumor targeting anticancer drug conjugates that contain a tumor recognition motif (homing device) are of high current relevance. Cryptophycins, naturally occurring cytotoxic cyclo-depsipeptides, have been modified by total synthesis to provide analogues suitable for conjugation to peptide-based homing devices. An array of functionalized beta(2)-amino acids was synthesized and incorporated into cryptophycins. All analogues proved to be highly active in the cytotoxicity assay using the human cervix carcinoma cell line KB-3-1 and its multidrug-resistant subclone KB-V1. Conformational analysis of cryptophycin-52 and two synthetic analogues was performed by NMR and MD methods to obtain information on the influence of the unit C configuration on the overall conformation. An azide-functionalized cryptophycin was connected by CuAAC to an alkyne-containing fluorescently labeled cyclic RGD-peptide as the homing device for internalization studies. Confocal fluorescence microscopy proved integrin-mediated internalization by endocytosis and final lysosomal localization of the cryptophycin prodrug.