N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline | 174649-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline
• 英文别名: 4-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-piperazine-1-carboxylic acid benzyl ester；4-[2-fluoro-4-[[(phenylmethoxy)carbonyl]amino]phenyl]-1-piperazinecarboxylic acid phenylmethyl ester；benzyl 4-(4-{[benzyloxycarbonyl]amino}-2-fluorophenyl)-1-piperazinecarboxylate；3-Fluoro-4-[4-(benzyloxycarbonyl)piperazino]phenylcarbamic acid benzyl ester；benzyl 4-[2-fluoro-4-(phenylmethoxycarbonylamino)phenyl]piperazine-1-carboxylate
• CAS: 174649-03-7
• 化学式: C₂₆H₂₆FN₃O₄
• 分子量: 463.509
• InChiKey: OPWCRBOOVRSYHY-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161 °C
• 沸点：
  592.3±50.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline 在 palladium on activated charcoal 吡啶 、 正丁基锂 、 二氯甲烷 、 氢气 、 三乙胺 、 甲胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 68.0h， 生成 N-[[(5S)-3-[3-氟-4-[4-(2-羟基乙酰基)-1-哌嗪基]苯基]-2-氧代-5-噁唑烷基]甲基]-乙酰胺
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of U-100592 and U-100766, Two Oxazolidinone Antibacterial Agents for the Potential Treatment of Multidrug-Resistant Gram-Positive Bacterial Infections

  摘要：

  Bacterial resistance development has become a very serious clinical problem for many classes of antibiotics. The 3-aryl-2-oxazolidinones are a relatively new class of synthetic antibacterial agents, having a new mechanism of action which involves very early inhibition of bacterial protein synthesis. We have prepared two potent, synthetic oxazolidinones, U-100592 and U-100766, which are currently in clinical development for the treatment of serious multidrug-resistant Gram-positive bacterial infections caused by strains of staphylococci, streptococci, and enterococci. The in vitro and in vivo (po and iv) activities of U-100592 and U-100766 against representative strains are similar to those of vancomycin. U-100592 and U-100766 demonstrate potent in vitro activity against Mycobacterium tuberculosis. A novel and practical asymmetric synthesis of (5S)-(acetamidomethyl)-2-oxazolidinones has been developed and is employed for the synthesis of U-100592 and U-100766. This involves the reaction of N-lithioarylcarbamates with (R)-glycidyl butyrate, resulting in excellent yields and high enantiomeric purity of the intermediate (R)-5-(hydroxymethyl)-2-oxazolidinones,

  DOI：

  10.1021/jm9509556
• 作为产物：
  描述：

  4-(4-Boc-哌嗪-1-基)-3-氟苯胺 在 盐酸 、 水 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 生成 N-carbobenzoxy-3-fluoro-4-(N-carbobenzoxypiperazin-1-yl)aniline
  参考文献：
  名称：

  [EN] BORON CONTAINING SMALL MOLECULES
  [FR] PETITES MOLÉCULES CONTENANT DU BORE

  摘要：

  这项发明提供了用于治疗细菌感染的新化合物，包含这些化合物的药物组合物，以及这些化合物与至少一种其他治疗有效剂的组合。

  公开号：

  WO2011037731A1

文献信息

• Amide-containing compound having improved solubility and method of improving the solubility of an amide-containing compound
  申请人：——

  公开号：US20040014967A1

  公开（公告）日：2004-01-22

  The present invention is directed to novel amide-containing compounds which have an improved solubility and a method of improving the solubility of amide-containing compounds. The amide-containing compounds include oxazolidinone compounds and the bioavailability of these oxazolidinone compounds is improved by improving the solubility thereof.

  本发明涉及具有改善溶解性的新型酰胺化合物，以及改善酰胺化合物溶解性的方法。这些酰胺化合物包括噁唑烷酮化合物，通过改善其溶解性来提高这些噁唑烷酮化合物的生物利用度。
• N-aryl-2-oxazolidinone-5-carboxamides and their derivatives
  申请人：——

  公开号：US20040147760A1

  公开（公告）日：2004-07-29

  The present invention provides antibacterial agents having the formulae I, II, and III described herein.

  本发明提供了具有以下式I、II和III的抗菌剂。
• [EN] N-ARYL-2-OXAZOLIDINONE-5-CARBOXAMIDES AND THEIR DERIVATIVES AND THEIR USE AS ANTIBACTERIALS<br/>[FR] N-ARYL-2-OXAZOLIDINONE-5-CARBOXAMIDES ET LEURS DERIVES ET UTILISATION DE CES COMPOSES COMME ANTIBACTERIENS
  申请人：UPJOHN CO

  公开号：WO2003072553A1

  公开（公告）日：2003-09-04

  Compounds of formula B-C-A-CO-NH-R1, wherein A is structure i, ii or iii: formulae (I), (II), (III). C is optionally substituted aryl or heteroaryl, and B is a specified cyclic moiety, or C and B together are a heterobicyclic moiety, are useful as antibacterial agents.

  公式为B-C-A-CO-NH-R1的化合物，其中A是结构i、ii或iii：公式(I)、(II)、(III)。C是可选择取代的芳基或杂环芳基，而B是特定的环状基团，或者C和B一起是一个杂双环基团，可用作抗菌剂。
• PREPARATION AND UTILITY OF SUBSTITUTED OXZOLIDINONES
  申请人：Gant Thomas G.

  公开号：US20080146573A1

  公开（公告）日：2008-06-19

  Disclosed herein are substituted oxazolidinones of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and the methods of their use thereof.

  本文披露了式I的取代氧唑啉酮，其制备方法，药物组合物以及其使用方法。
• Dynamic kinetic resolution of epichlorohydrin via enantioselective catalytic ring opening with TMSN3. Practical synthesis of aryl oxazolidinone antibacterial agents
  作者：Scott E. Schaus、Eric N. Jacobsen

  DOI：10.1016/0040-4039(96)01835-7

  日期：1996.10

  The dynamic kinetic resolution of racemic epichlorohydrin has been achieved via enantioselective asymmetric ring opening with TMSN3 catalyzed by the (salen)Cr(III)N3 complex 1. The resulting 3-azido-1-chloro-2-trimethylsiloxypropane product was obtained in high enantiomeric purity and incorporated into the synthesis of U-100592, a representative from a class of highly-promising aryl oxazolidinone antibacterial

  通过（salen）Cr（III）N 3络合物1催化的TMSN 3对映选择性不对称开环，实现了外消旋环氧氯丙烷的动力学动力学拆分。以高对映体纯度获得所得的3-叠氮基-1-氯-2-三甲基甲硅烷氧基丙烷产物，并将其掺入U-100592的合成中，U-100592是一类高度有前景的芳基恶唑烷酮抗菌剂的代表。