2-(3-溴-5-异恶唑基)环氧乙烷 | 76596-56-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-(3-溴-5-异恶唑基)环氧乙烷
• 英文名称: 2-(3-bromo-5-isoxazolyl)oxirane
• 英文别名: 3-bromo-5-oxiran-2-ylisoxazole；2-(3-bromo-isoxazol-5-yl)-oxirane；3-Bromo-5-(oxiran-2-yl)-1,2-oxazole
• CAS: 76596-56-0
• 化学式: C₅H₄BrNO₂
• 分子量: 189.996
• InChiKey: UZUMNQDSSAUUHV-UHFFFAOYSA-N

物化性质

• 沸点：
  120-125 °C(Press: 0.5 Torr)
• 密度：
  1.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-溴-5-异恶唑基)环氧乙烷 以 乙醇 为溶剂， 反应 16.0h， 生成 1-(3-溴-1,2-恶唑-5-基)-2-(叔丁基氨基)乙醇盐酸盐
  参考文献：
  名称：

  Chiarino; Fantucci; Carenzi, Farmaco, Edizione Scientifica, 1986, vol. 41, # 6, p. 440 - 453

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3-溴-5-异恶唑基)-2-溴乙醇 以 苯 为溶剂， 生成 2-(3-溴-5-异恶唑基)环氧乙烷
  参考文献：
  名称：

  1-(3-Bromo-isoxazol-5-yl)-2-tert.butylaminoethanol

  摘要：

  本发明公开了一种新的异噁唑衍生物及其制备方法。公开了具有治疗活性的1-(3-溴异噁唑-5-基)-2-叔丁基氨基乙醇，特别是具有支气管扩张作用的药物，以及从3-溴-5-异噁唑羧酸制备该化合物的方法。还公开了新的中间体化合物以及含有新异噁唑衍生物的药物组合物。

  公开号：

  US04276299A1

文献信息

• Novel chiral isoxazole derivatives: Synthesis and pharmacological characterization at human β-adrenergic receptor subtypes
  作者：Clelia Dallanoce、Fabio Frigerio、Marco De Amici、Sandra Dorsch、Karl-Norbert Klotz、Carlo De Micheli

  DOI：10.1016/j.bmc.2007.01.056

  日期：2007.4

  Isoxazole derivative (+/-)-4 and the three pairs of stereoisomeric 3-bromo-isoxazolyl amino alcohols (S,R)-(-)-7a/(R,R)(+)-7b, (S, R)-(-)-8a/(R, R)-(+)-8b, and (S, R)-(-)-9a/(R, R)-(+)-9b were synthesized and assayed for their affinity and efficacy at human beta(1)-, beta(2)-, and beta(3)-adrenergic receptors (beta-ARs) in membranes from Chinese hamster ovary (CHO) cells stably transfected with the respective receptor subtype. Whereas derivative ()-4 did not bind at all three P-ARs, stereoisomers (S, R)-7a-(S, R)-9a behaved as high-affinity ligands at beta(1)- and, particularly, at beta(2)-ARs (K-i 2.82-66.7 nM). The Ki values of isomers (R,R)-7b-(R,R)-9b at beta(1)- and beta(2)-subtypes were about 30-100 times higher than those of their (S, R)-7a-9a counterparts, indicating a sizable stereochemical effect. The affinity at beta(3)-ARs was negligible for all the investigated compounds. When submitted to a functional assay, the three stereoisomeric pairs showed a comparable pattern of efficacy at all three beta-AR subtypes. The highest value of efficacy (75-90%) was observed at beta(2)-ARs, whereas all compounds behaved as partial agonists (30-60%) at the beta(3)-subtype. The lowest degree of efficacy (15-35%) was found at beta(1)-ARs. The affinity/efficacy profile of the derivatives under study has been compared with that of the two model compounds, Broxaterol [(+/-)-1] and BRL 37344 [(+/-)-6]. (c) 2007 Elsevier Ltd. All rights reserved.
• CHIARINO D.; FANTUCCI M.; CARENZI A.; DELLA BELLA D.; FRIGENI V.; SALA R., FARMACO. ED. SCI., 41,(1986) N 6, 440-453
  作者：CHIARINO D.、 FANTUCCI M.、 CARENZI A.、 DELLA BELLA D.、 FRIGENI V.、 SALA R.

  DOI：——

  日期：——