1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol | 1189378-18-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
• 英文别名: 1-Bromo-3-(5-methyl-2-propan-2-ylphenoxy)propan-2-ol；1-bromo-3-(5-methyl-2-propan-2-ylphenoxy)propan-2-ol
• CAS: 1189378-18-4
• 化学式: C₁₃H₁₉BrO₂
• 分子量: 287.197
• InChiKey: RCQDNLLWUPLEAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-羟乙基哌嗪 、 1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以71%的产率得到1-(4-(2-hydroxyethyl)piperazin-1-yl)-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  A novel class of small molecule inhibitors with radioprotective properties

  摘要：

  The goal of this study was to develop novel radioprotective agents targeting the intrinsic apoptotic pathway and thus decreasing the radiation-induced damage. For that purpose, we designed, synthesized and analyzed ten new compounds based on the 1-(4-(2-hydroxyethyl)piperazin-l-yl)-3-phenoxypropan-2-ol leading structure. The cytotoxicity of the newly synthesized substances was tested in vitro on cell lines derived from different progenitor cells by WST-1 proliferation assay. mTr test was utilized to assess half-maximal inhibitory concentrations and maximum tolerated concentrations of novel compounds in A-549 cells. Screening for radioprotective properties was performed using flow-cytometry in MOLT-4 cells exposed to Co-60 ionizing gamma radiation. Selected candidates underwent in vivo testing in C57BI/6J mice having a positive impact on their immunological status. In summary, we report here promising compounds with radioprotective effect in vivo. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111606
• 作为产物：
  描述：

  2-[(2-异丙基-5-甲基苯氧基)甲基]环氧乙烷 在 lithium bromide 、 copper(ll) bromide 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到1-bromo-3-(2-isopropyl-5-methylphenoxy)propan-2-ol
  参考文献：
  名称：

  Maciejewski; Poltorak; Kaminska, Polish Journal of Chemistry, 2009, vol. 83, # 4, p. 595 - 604

  摘要：

  DOI：

文献信息

• Lipase resolution of new (±)-3-aryloxy-1-halogenopropan-2-ols: Versatile building blocks for β-adrenergic receptor antagonists
  作者：Maciej Maciejewski、Krzysztof Półtorak、Janina E. Kamińska

  DOI：10.1016/j.molcatb.2009.11.004

  日期：2010.3

  Using two commercial immobilized lipases Lipozyme(R) TL and Novozym(R) 435 effective kinetic resolution of several novel 3-aryloxy-1-halogenopropan-2-ols was achieved by acyl transfer reaction in organic solvents, yielding both enantiomers with 89-99% ee. In preparative resolutions carried out in tert-butyl methyl ether at 25 degrees C with vinyl acetate as acyl donor enantioselectivity ratio E was from 64 to 99. The resolved enantiomers were successfully used as chiral building blocks in the synthesis of new 1-alkylamino-3-aryloxypropan-2-ols, by nucleophilic halogen substitution with isopropylamine and tert-butylamine. The obtained products will be evaluated in vitro as potential new beta-adrenergic receptors antagonists. (C) 2009 Elsevier B.V. All rights reserved.
• A novel class of small molecule inhibitors with radioprotective properties
  作者：Jan Marek、Ales Tichy、Radim Havelek、Martina Seifrtova、Alzbeta Filipova、Lenka Andrejsova、Tomas Kucera、Lukas Prchal、Lubica Muckova、Martina Rezacova、Zuzana Sinkorova、Jaroslav Pejchal

  DOI：10.1016/j.ejmech.2019.111606

  日期：2020.2

  The goal of this study was to develop novel radioprotective agents targeting the intrinsic apoptotic pathway and thus decreasing the radiation-induced damage. For that purpose, we designed, synthesized and analyzed ten new compounds based on the 1-(4-(2-hydroxyethyl)piperazin-l-yl)-3-phenoxypropan-2-ol leading structure. The cytotoxicity of the newly synthesized substances was tested in vitro on cell lines derived from different progenitor cells by WST-1 proliferation assay. mTr test was utilized to assess half-maximal inhibitory concentrations and maximum tolerated concentrations of novel compounds in A-549 cells. Screening for radioprotective properties was performed using flow-cytometry in MOLT-4 cells exposed to Co-60 ionizing gamma radiation. Selected candidates underwent in vivo testing in C57BI/6J mice having a positive impact on their immunological status. In summary, we report here promising compounds with radioprotective effect in vivo. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Maciejewski; Poltorak; Kaminska, Polish Journal of Chemistry, 2009, vol. 83, # 4, p. 595 - 604
  作者：Maciejewski、Poltorak、Kaminska

  DOI：——

  日期：——