(R,S)-3-(oxiranylmethyl)-2-oxazolidinone | 21899-19-4

• 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: (R,S)-3-(oxiranylmethyl)-2-oxazolidinone
• 英文别名: 1-glycidyl-2-oxazolidinone；3-(oxiranylmethyl)-2-oxazolidinone；3-(Oxiran-2-ylmethyl)-1,3-oxazolidin-2-one
• CAS: 21899-19-4
• 化学式: C₆H₉NO₃
• mdl: MFCD11131215
• 分子量: 143.142
• InChiKey: AZTKGGHLZQXCTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  42.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,S)-3-(oxiranylmethyl)-2-oxazolidinone 在 氢溴酸 、 caesium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 27.13h， 生成 1-(1-氮丙啶基)-3-(2-硝基-1H-咪唑-1-基)-2-丙醇
  参考文献：
  名称：

  Dual-function radiosensitizers. .alpha.-[[(2-Bromoethyl)amino]methyl]-2-nitro-1H-imidazole-1-ethanol and related compounds: preparation via an aziridine equivalent

  摘要：

  An improved synthesis of the dual-function radiosensitizer alpha-[[2-bromoethyl)amino]methyl]-2-nitro-H-1-imidazole-1-ethanol (2, RB 6145) has been developed. Previously, the synthetic difficulties associated with this compound limited its attractiveness as a clinical candidate, although its radiosensitizing activity in preclinical models warranted its further development. The synthesis described uses a 2-oxazolidinone as an aziridine equivalent and provides 2 in 47% yield.

  DOI：

  10.1021/jm00107a047
• 作为产物：
  描述：

  2-唑烷酮 、 环氧氯丙烷 在 sodium 作用下， 以 甲苯 为溶剂， 以34%的产率得到(R,S)-3-(oxiranylmethyl)-2-oxazolidinone
  参考文献：
  名称：

  Haloalkylaminomethyl-2-nitro-1H-imidazoles

  摘要：

  本发明是一种新型的硝基咪唑类化合物，可用作放射增敏剂或化学增敏剂，用于治疗缺氧肿瘤细胞。此外，本发明还涉及一种新型的制备已知和新型硝基咪唑类化合物的方法，其中包含新型的中间体。该方法具有优势，可以减少制程步骤的数量，提高产量，并且在产品中提供更大的安全性和对立体异构体的更大控制。

  公开号：

  US04954515A1

文献信息

• Synthesis of the enantiomers of the dual function 2-nitroimidazole radiation sensitizer RB 6145
  作者：Anthony D. Sercel、Vladimir G. Beylin、Mark E. Marlatt、Boguslawa Leja、H. D. Hollis Showalter、André Michel

  DOI：10.1002/jhet.5570430625

  日期：2006.11

  described for the synthesis of racemic 2-nitroimidazole radiation sensitizer RB-6145 (2a) and each of its corresponding (R)- and (S)-enantiomers (2b and 2c, respectively). The synthesis of each enantiomer commences with the appropriate chiral epichlorohydrin and utilizes a novel application of 3-trimethylsilyl-2-oxazolidinone (3b) as a mild, safe surrogate for highly toxic aziridine. The synthesis of the (R)-enantiomer

  描述了用于合成外消旋2-硝基咪唑辐射敏化剂RB-6145（2a）及其相应的（R）-和（S）-对映体（分别为2b和2c）的短而有效的途径。每个对映异构体的合成均始于适当的手性表氯醇，并利用3-三甲基甲硅烷基-2-恶唑烷酮（3b）的新颖应用作为温和，安全的高毒性氮丙啶的替代物。（R）-对映异构体（2b）的合成已成功扩大规模，可为早期临床前评估提供几千量的材料。
• 10a-Azalide Compound
  申请人：Sugimoto Tomohiro

  公开号：US20090281292A1

  公开（公告）日：2009-11-12

  [Object]: To provide a compound having a novel structure effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria. [Solution]: A novel 10a-azalide compound represented by the formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof, or an intermediate for the preparation of the same. The compound of the present invention has superior antibacterial activity against Hemophilus influenzae , erythromycin resistant pneumococci and the like, and therefore, the compound can be used as a therapeutic agent of infectious diseases.

  【目标】提供一种具有新结构的化合物，对流感嗜血杆菌和红霉素耐药菌（例如耐药肺炎球菌和链球菌）以及传统的红霉素敏感菌具有有效作用。 【解决方案】本发明提供了一种新型10a-氮杂环十六元化合物，其化学式为（I），其药学上可接受的盐或其溶剂化物，或其制备的中间体。该化合物对流感嗜血杆菌、红霉素耐药性肺炎球菌等具有卓越的抗菌活性，因此可以作为治疗传染病的药物。
• A new process for the synthesis of novel and known nitroimidazoles which are useful as sensitizing agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0375951A1

  公开（公告）日：1990-07-04

  The present invention is novel nitroimidazoles useful as radiosensitizing or chemosensitizing agents in the treatment of hypoxic tumor cells. Also, the present invention is a novel process for preparing both known and novel nitroimidazoles having novel intermediates. The process advantageously reduces the number of process steps, provides increased yield with both greater safety and greater control of stereoisomerism in the products.

  本发明是新型硝基咪唑，可用作治疗缺氧性肿瘤细胞的放射增敏剂或化疗增敏剂。此外，本发明是一种新型工艺，用于制备具有新型中间体的已知和新型硝基咪唑。该工艺的优点是减少了工艺步骤的数量，提高了产率，同时提高了安全性，并能更好地控制产品的立体异构性。
• 10a-AZALIDE COMPOUND
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：EP1985620A1

  公开（公告）日：2008-10-29

  [Object]: To provide a compound having a novel structure effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria. [Solution]: A novel 10a-azalide compound represented by the formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof, or an intermediate for the preparation of the same. The compound of the present invention has superior antibacterial activity against Hemophilus influenzae, erythromycin resistant pneumococci and the like, and therefore, the compound can be used as a therapeutic agent of infectious diseases.

  [目的]：提供一种具有新型结构的化合物，该化合物对流感嗜血杆菌和红霉素耐药菌（例如耐药肺炎球菌和链球菌）以及传统的红霉素敏感菌有效。 [解决方案］一种由式（I）代表的新型 10a-azalide 化合物、其药学上可接受的盐或其溶液，或制备其的中间体。本发明的化合物对流感嗜血杆菌、耐红霉素肺炎球菌等具有优异的抗菌活性，因此可用作传染性疾病的治疗剂。
• SUTO, MARK J.;STIER, MICHAEL A.;WERBEL, LESLIE M., J. MED. CHEM., 34,(1991) N, C. 1207-1209
  作者：SUTO, MARK J.、STIER, MICHAEL A.、WERBEL, LESLIE M.

  DOI：——

  日期：——