(S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone | 203739-34-8

• 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: (S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone
• 英文别名: (S)-4-benzyl-3-(6-bromohexanoyl)oxazolidin-2-one；(4S)-4-benzyl-3-(6-bromohexanoyl)-1,3-oxazolidin-2-one
• CAS: 203739-34-8
• 化学式: C₁₆H₂₀BrNO₃
• 分子量: 354.244
• InChiKey: WRATUSCTLDXUMP-AWEZNQCLSA-N

物化性质

• 沸点：
  488.2±28.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone 在 sodium azide 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 75.0h， 生成 (4S)-4-benzyl-3-<(2'R)-2'-<(tert-butoxycarbonyl)methyl>-6'-azidohexanoyl>-2-oxazolidone
  参考文献：
  名称：

  Conjugates of Modified Cryptophycins and RGD-Peptides Enter Target Cells by Endocytosis

  摘要：

  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.

  DOI：

  10.1021/jm301346z
• 作为产物：
  描述：

  6-溴己酰氯 、 (S)-4-苄基-2-唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.17h， 以76%的产率得到(S)-4-benzyl-3-(6-bromo-1-oxohexyl)-2-oxazolidinone
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b

文献信息

• [EN] FUROPYRIDINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE FUROPYRIDINE ET SES UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2011131709A1

  公开（公告）日：2011-10-27

  The present invention provides a compound of formula (I); a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种式(I)的化合物；一种用于制造本发明化合物的方法，以及其治疗用途。本发明还提供了药理活性剂的组合和药物组合物。
• Asymmetric Synthesis of ω‐Bromo‐2(S)‐Methyl Acids as Precursors for Novel Arginine, Lysine, and Mercapto Residues
  作者：M. Kyle Hadden、Kyle P. Kokko、Thomas A. Dix

  DOI：10.1081/scc-200061668

  日期：2005.6.1

  Abstract A series of ω‐bromo‐2(S)‐methyl acids has been synthesized as precursors of novel arginine (Arg), lysine (Lys), and mercapto analogues. These intermediates contain α‐methyl groups and are designed to mask the N‐terminal amine when incorporated in pharmaceutically relevant peptides.

  摘要 已经合成了一系列 ω-溴-2(S)-甲基酸作为新型精氨酸 (Arg)、赖氨酸 (Lys) 和巯基类似物的前体。这些中间体含有 α-甲基，当掺入药物相关的肽中时，它们旨在掩盖 N 端胺。
• Furopyridine compounds and uses thereof
  申请人：BARNES David

  公开号：US20120015907A1

  公开（公告）日：2012-01-19

  The present invention provides a compound of formula I; a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了化合物I的公式；一种制造本发明化合物的方法及其治疗用途。本发明还提供了具有药理活性剂的组合物和制药组合物。
• [EN] NON-NATURAL AMINO ACIDS<br/>[FR] ACIDES AMINES NON NATURELS
  申请人：UNIV SOUTH CAROLINA

  公开号：WO2006009902A3

  公开（公告）日：2006-12-28
• Asymmetric synthesis of ω-bromo-2(S)-azido acids as precursors for the synthesis of novel amino acids
  作者：Joseph T. Lundquist、Thomas A. Dix

  DOI：10.1016/s0040-4039(97)10608-6

  日期：1998.2

  A series of omega-bromo-2(S)-azido acids with side-chain lengths ranging from 3-5 methylene units has been synthesized. These intermediates enable the facile synthesis of chiral non-natural amino acids containing virtually any nucleophile capable of substituting the omega-bromo group. (C) 1998 Elsevier Science Ltd. All rights reserved.