3-allyl-5-hydroxymethyloxazolidin-2-one

• 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: 3-allyl-5-hydroxymethyloxazolidin-2-one
• 英文别名: N-allyl-5-hydroxymethyloxazolidin-2-one；3-Allyl-5-hydroxymethyl-oxazolidin-2-one；5-(hydroxymethyl)-3-prop-2-enyl-1,3-oxazolidin-2-one
• 化学式: C₇H₁₁NO₃
• mdl: MFCD09033590
• 分子量: 157.169
• InChiKey: MFXZKUJCSHVOMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-allyl-5-hydroxymethyloxazolidin-2-one 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 3-allyl-5-(4-benzhydryl-piperazin-1-ylmethyl)-oxazolidin-2-one
  参考文献：
  名称：

  Bioisosteric Replacement and Related Analogs in the Design, Synthesis and Evaluation of Ligands for Muscarinic Acetylcholine Receptors

  摘要：

  之前关于一系列基于内酯的毒蕈碱配体的结构-活性关系研究中，确定了一种含有二苯甲基哌嗪基团的领先化合物（4；IC50 = 340 nM）。本研究的目的是探讨1,3-苯并二氧杂环、4,4-二乙基取代的四氢呋喃、5-取代的噁唑烷酮和色烯作为新系列毒蕈碱配体中内酯环的生物等效替代物。该方法提供了具有改善的抑制率值的化合物，并识别出一种非选择性的毒蕈碱配体，其IC50值为280 nM。将讨论这一新系列的结构-活性关系。选定的化合物在初步实验中进行亚型选择性评估，结果发现它们是非选择性的。

  DOI：

  10.2174/15734064113096660043
• 作为产物：
  描述：

  司维拉姆杂质 、 碳酸二乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-allyl-5-hydroxymethyloxazolidin-2-one
  参考文献：
  名称：

  Enhanced cellular uptake by “pharmaceutically oriented devices” of new simplified analogs of Linezolid with antimicrobial activity

  摘要：

  The aim of the present study was to enhance cellular uptake of simplified analogs of Linezolid by their incorporation into suitable delivery devices in order to improve the antimicrobial activity of these novel synthesized oxazolidin-2-one derivatives. The oxazolidin-2-one derivatives were synthesized by developing a rather simple one-pot reaction starting from oxiranylmethanol and several primary amines. Three delivery devices were prepared by following different synthetic approaches, such as single-step free radical grafting, precipitation polymerization and nano-emulsion. Finally, the antimicrobial activity of the novel synthesized compounds, without any vehicle and after their incorporation into the delivery devices, was evaluated against Escherichia coli and Saccharomyces cerevisiae by performing time-kill analyses. The synthesized oxazolidinones exhibited modest antimicrobial activity against E. coli and S. cerevisiae (MIC 16 vg/mL). A good activity was, instead, highlighted after their incorporation into the prepared delivery devices (lecithin-based nano-emulsion, poly(N-vinyl-pyrrolidone)-methacrylic acid grafted copolymer and spherical polymeric nanoparticles) (MIC < 4 vg/mL). The incorporation into suitable vehicles, indeed, reduced by 4 times the normal MICs of the newly synthesized oxazolilidin-2-ones and represents an effective strategy to overcome cellular penetration constraints. 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2013.11.048

文献信息

• [EN] DISUBSTITUTED OXAZOLIDIN-2-ONES 5-HYDROXYTRYPTAMINE RECEPTOR 2B ACTIVITY MODULATORS<br/>[FR] OXAZOLIDIN-2-ONES DISUBSTITUÉES, MODULATEURS DE L'ACTIVITÉ DU RÉCEPTEUR 2B DE 5-HYDROXYTRYPTAMINE
  申请人：UNIV TEMPLE

  公开号：WO2014085413A1

  公开（公告）日：2014-06-05

  Pharmaceutical compositions of the invention comprise disubstituted oxazolidin-2-ones derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 2b activity.

  本发明的药物组合物包括二取代氧唑啉-2-酮衍生物，具有疾病修饰作用，用于治疗与5-羟色胺受体2b活性失调相关的疾病。
• Convenient Synthesis of Oxazolidinones by the Use of Halomethyloxirane, Primary Amine, and Carbonate Salt
  作者：Yumiko Osa、Yuka Hikima、Yoko Sato、Kouichi Takino、Yoshihiro Ida、Shuichi Hirono、Hiroshi Nagase

  DOI：10.1021/jo0501644

  日期：2005.7.1

  Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate

  伯胺在碱（例如DBU或TEA）的存在下与碳酸盐（Na 2 CO 3，K 2 CO 3，Cs 2 CO 3和Ag 2 CO 3）和卤代甲基环氧乙烷反应，以高收率得到恶唑烷酮。在这些碳酸盐中使用K 2 CO 3在该合成中获得了最佳的收率。提出了一种反应机理，即恶唑烷酮经由双环[2.2.1]中间体从恶嗪酮酮中间体获得。本反应可广泛用于方便地合成有用的N-取代的恶唑烷酮和手性恶唑烷酮。
• Method of preparing a heterocyclic intermediate for the production of optically active aryloxysubstituted vicinal aminoalcohols
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0647633A1

  公开（公告）日：1995-04-12

  The invention relates to a method of preparing a heterocyclic intermediate of the general formula wherein    X is a carbonyl group, a thiocarbonyl group, a (C₁-C₁₀)(ar)alkylidene group or a dihydrocarbylsilyl group,    R is a straight or branched (C₁-C₁₀)alkyl group, optionally substituted with halogen, hydroxy, (C₁-C₄)alkoxy or protected hydroxy, or a phenyl(C₁-C₃)alkyl or heteroaryl(C₁-C₃)alkyl group, which groups are optionally substituted with 1-3 substituents, selected from the group consisting of hydroxy, (C₅-C₁₂)cycloalkyl, amino, nitro, halogen, cyano, alkoxy, alkylcarbonyloxy, alkylcarbonylamino, alkylsulphonylamino, alkylsulphonyl, alkylcarbonyl, and alkyl, wherein the alkyl groups have 1-5 carbon atoms, and which intermediate has either the R or the S configuration, by subjecting an optically active cyanohydrin of the general formula to a reduction-transimination-reduction sequence, using R - NH₂ as the primary amine, followed by a cyclization reaction and, finally, by an ozonolysis-reduction sequence.

  本发明涉及一种制备杂环中间体的方法，其通式如下：其中X为羰基，硫代羰基，(C₁-C₁₀)(芳)烷基亚甲基或二氢基碳基硅基，R为直链或支链(C₁-C₁₀)烷基，可选用卤素、羟基、(C₁-C₄)烷氧基或保护羟基进行取代，或苯基(C₁-C₃)烷基或杂环芳基(C₁-C₃)烷基，这些基团可选用1-3个取代基进行取代，所述取代基选自羟基、(C₅-C₁₂)环烷基、氨基、硝基、卤素、氰基、烷氧基、烷基羰氧基、烷基羰基氨基、烷基磺酰胺基、烷基磺酰基、烷基羰基和烷基，其中烷基含有1-5个碳原子，该中间体具有R或S构型，通过将手性氰醇通式的还原-转移-还原序列，使用R-NH₂作为主要胺，然后进行环化反应，最后进行臭氧化-还原序列。
• DISUBSTITUTED OXAZOLIDIN-2-ONES 5-HYDROXYTRYPTAMINE RECEPTOR 2B ACTIVITY MODULATORS
  申请人：TEMPLE UNIVERSITY - OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCATION

  公开号：US20150291539A1

  公开（公告）日：2015-10-15

  Pharmaceutical compositions of the invention comprise disubstituted oxazolidin-2-ones derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 2b activity.

  本发明的制药组合物包括二取代噁唑烷-2-酮衍生物，具有改变疾病作用，用于治疗与5-羟色胺受体2b活性失调相关的疾病。
• Process for production of optically active oxazolidinone derivative
  申请人：KANEGAFUCHI KAGAKU KOGYO KABUSHIKI KAISHA

  公开号：EP0101076A2

  公开（公告）日：1984-02-22

  This invention shows a process for preparing the optically active oxazolidinone derivative [(S)-I] by utilizing microorganisms or engymes having a stereo-selective esterase activity capable of asymmetrically hydrolyzing the racemates of the acyloxyoxazolidinone derivative [(R.S)-Il], by separating the unreacted compound [(S)-II] from the hydrolyzed compound [(R)-I] and by hydrolyzing the compound [(S)-II]. The compounds are useful as intermediates for preparing optically active β-adrenergic blocking agents.

  本发明展示了一种制备光学活性噁唑烷酮衍生物[(S)-I]的工艺，其方法是利用具有立体选择性酯酶活性、能够不对称水解酰氧基噁唑烷酮衍生物[(R.S)-Il]外消旋体的微生物或酵母，将未反应的化合物[(S)-II]与水解的化合物[(R)-I]分离，并水解化合物[(S)-II]。这些化合物可作为制备具有光学活性的β-肾上腺素能阻断剂的中间体。