CAS: 168828-90-8; (S)-5-(Aminomethyl)-3-(3-Fluoro-4-Morpholinophenyl)Oxazolidin-2-One

该化合物是合成线性索利德(一种氧化氮素类抗生素)的关键中间体,该化合物是通过线性索利德酶或化学脱氧而形成的,保留了进一步衍生或分析应用所需的核心结构特征,其主要优势在于其作为制药研究前体的作用,能够开发具有潜在增强效力或降低抗药性特征的新抗生素类比. Deacetyl Linezolid在代谢研究中也很宝贵,有助于了解线性亚利德的药性动力学和降解途径.高纯度和稳定性使其适合于在受控制的实验室和工业环境中使用.

英文名称(S)-5-(Aminomethyl)-3-(3-Fluoro-4-Morpholinophenyl)Oxazolidin-2-One
中文名称利奈唑胺碱
IUPAC名称(S)-5-(aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one
其它别名(5S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)-1,3-oxazolidin-2-one; (S)-(-)-5-Aminomethyl-3-(3-fluoro-4-morpholinophenyl)-1,3-oxazolidin-2-one; (S)-5-(Aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one; (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine; Deacetyl Linezolid; InterMediate of Linezolid
CAS编号168828-90-8
MFCD编号:MFCD18379308
FDA UNII编号:96T3Q5LLFR
分子式:C14H18FN3O3
分子量:295.31
产品CID: 852504
产品分类分析化学 → 标准品 → 药典标准品和杂质标准品

相似结构搜索
InChIKey: VXIWZOWWQMRVRF-NSHDSACASA-N
InChI=1S/C14H18FN3O3/c15-12-7-10(18-9-11(8-16)21-14(18)19)1-2-13(12)17-3-5-20-6-4-17/h1-2,7,11H,3-6,8-9,16H2/t11-/m0/s1…
计算化学: 氢键受体数6.0氢键供体数1.0可旋转键数3.0

物理性质

熔点95-97°C
沸点480.0±45.0 °C at 760 mmHg
闪点244.1±28.7 °C
密度1.3±0.1 g/cm3
pKa:8.96±0.29(预测)
PSA:68.03
LogP:0.69
折射率1.572
蒸汽压0.0±1.2 mmHg at 25°C
溶解性Chloroform (Slightly), Methanol (Slightly)
外观形态类白色至淡黄色固体
储存条件请置于阴暗处, 惰性气氛中,2-8°C
产品应用该化合物用于抗菌菌菌剂的线性叶杂质(L466500).

上下游产品

合成工艺路线路线简述

合成目标产物 (S)-N-[[3-[3-Fluoro-4-(4-Morpholinyl)Phenyl]-2-Oxo-5-Oxazolidinyl]Methyl]Amine 主要起始原料 Linezolid
(文献来源)合成步骤主要原料 Linezolid

利奈唑胺置于盐酸体系中,用甲醇用作溶剂,以99%的收率获得利奈唑胺碱
参考文献:用恶唑烷酮类抗菌剂逃避大肠杆菌的外排和渗透屏障的化合物设计指南:改善全细胞革兰氏阴性活性的一般方法的测试案例
标题:用恶唑烷酮类抗菌剂逃避大肠杆菌的外排和渗透屏障的化合物设计指南:改善全细胞革兰氏阴性活性的一般方法的测试案例
摘要:先前,我们报告了通过完全专注于c环修饰的系统性药物化学活动,努力提高恶唑烷酮类抗生素中革兰氏阴性抗菌活性的结果.在该系列文章中,我们着手测试是否可以通过设计类似物使其驻留在与革兰氏阴性活性相关的特定特性范围内来合理地克服大肠杆菌外膜固有的外排和渗透障碍:I)低分子量(<400),Ii)高极性(clogd 7.4<1),和iii)ph 7.4时的两性离子特性.实际上,我们观测到只有存在于这些限制范围内的类似物才能克服这些障碍.本文中,我们报告了一项平行努力的结果,出于相同的目的,我们探索了支架中所有三个环的结构变化.针对大肠杆菌和金黄色葡萄球菌的诊断mic板测试了化合物菌株以确定结合结构修饰在克服om障碍和弥合物种之间的效力差距方面的影响.结果表明,将带电荷的部分分布在两个环上也有利于避免外膜屏障.重要的是,对由此和先前研究获得的结构-渗透关系(spr)进行的分析表明,除分子量,极性和两性
Doi:10.1016/j.Bmcl.2017.10.018

海关参考信息

2905122000-异丙醇
2909110000-乙醚
2912110000-甲醛
2915110000-甲酸
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-9567307-B2
优先权日:2011-01-07
标题:Amination of aryl alcohol derivatives
发明人：GARG NEIL K; RAMGREN STEPHEN D; SILBERSTEIN AMANDA L; QUASDORF KYLE W
权利人:GARG NEIL K; RAMGREN STEPHEN D; SILBERSTEIN AMANDA L; QUASDORF KYLE W; UNIV CALIFORNIA
摘要:Embodiments of the invention provide methods and materials for chemical cross-coupling reactions that utilize aryl alcohol derivatives as cross-coupling partners. Embodiments of the invention include methods for the amination of aryl sulfamates and carbamates, which are attractive cross-coupling partners, particularly for use in multistep synthesis. Illustrative embodiments include versatile means to use simple derivatives of phenol as precursors to polysubstituted aryl amines, as exemplified by a concise synthesis of the antibacterial drug linezolid.

专利号:US-6743811-B2
优先权日:1999-07-28
标题:Oxazalidinone compounds and methods of preparation and use thereof
发明人：GORDEEV MIKHAIL F; LUEHR GARY W; PATEL DINESH V; GADWOOD ROBERT C
权利人:UPJOHN CO
摘要:Oxazolidinones and methods for their synthesis are provided. Further provided are methods of making biologically active oxazolidinones as well as pharmaceutically acceptable compositions comprising the oxazolidinones. Oxazolidinones as disclosed herein can be readily synthesized and used in a variety of applications including use as antimicrobial agents. In one embodiment, a variety of thioamidomethyloxazolidinones and methods for their synthesis and use are provided.

专利号:US-7179794-B2
优先权日:1998-06-08
标题 :Multivalent macrolide antibiotics
发明人：GRIFFIN JOHN H; PACE JOHN L
权利人:THERAVANCE INC
摘要:Disclosed are multibinding compounds which include macrolide antibiotics, aminoglycosides, lincosamides, oxazolidinones, streptoramins, tetracycline and/or other compounds which bind to bacterial ribosomal RNA and/or to one or more proteins involved in ribosomal protein synthesis in the bacterium, which are useful in treating bacterial infections. The compounds adversely affect protein expression and have an antibacterial effect. The multibinding compounds of this invention containing from 2 to 10 ligands covalently attached to one or more linkers. Each ligand is macrolide antibiotic, aminoglycoside, lincosamide, oxazolidinone, streptogramin, tetracycline or other compound which binds to bacterial ribosomal RNA and/or one or more proteins involved in ribosomal protein synthesis in the bacterium.

专利号:CN-109265407-B
优先权日:2018-10-23
标题:Synthesis method of bislinezolid

专利号:WO-2016095877-A1
优先权日:2014-12-17
标题 :Substituted 2-(2-phenylhydrazinyl)pyrazine, process for its preparation, its use and a pharmaceutical composition containing the same
发明人：DOLEZAL MARTIN; ZITKO JAN; JANDOUREK ONDREJ; SERVUSOVA-VANASKOVA BARBORA
权利人:UNIV KARLOVA
摘要:Substituted 2-(2-phenylhydrazinyl)pyrazine of general formula I, wherein each R 1 , R 2 is independently H or CN; R 3 is CH 3 or CONH 2 ; each R 4 , R 5 , R 6 , R 7 , R 8 is independently H, CI, or NO 2 . The invention further provides a method for preparing such substances, in which the appropriate substituted chloropyrazine is treated with a substituted phenylhydrazine under conditions of microwave synthesis. The compounds of general formula I are characterized by their low toxicity and high activity against mycobacteria. They can also be used in pharmaceutical preparations as antitubercular drugs.