(RS)-1-bromo-3-(1-naphthyloxy)-2-propanol | 2007-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (RS)-1-bromo-3-(1-naphthyloxy)-2-propanol
• 英文别名: 1-naphthoxy-3-bromo-2-propanol；1-bromo-3-(1-naphthalenyloxy)-2-propanol；1-Bromo-3-[(naphthalen-1-yl)oxy]propan-2-ol；1-bromo-3-naphthalen-1-yloxypropan-2-ol
• CAS: 2007-16-1
• 化学式: C₁₃H₁₃BrO₂
• 分子量: 281.149
• InChiKey: JDXFHGPXCUZGFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2909499000

反应信息

• 作为反应物：
  描述：

  (RS)-1-bromo-3-(1-naphthyloxy)-2-propanol 在 tripropylammonium fluorochromate (VI) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以70%的产率得到1-bromo-3-(1-naphthyloxy)-2-propanone
  参考文献：
  名称：

  Preparation of halohydrin β-blocker precursors using yeast-catalysed reduction

  摘要：

  The preparation of halohydrin beta -blocker precursors using yeast-catalysed reduction of alpha -haloketones was performed. The influence in the yield and e.e, of several process variables was analysed. The (S)-enantioselectivity observed with Saccharomyces cerevisiae can be changed to (R)-enantioselectivity using methyl vinyl ketone as selective inhibitor (25 mM). Using resting fresh cells better yields and e.e.s are observed than using growing cells. Yarrowia lipolytica 1240 resting cells gave 87% yield of (S)-1-chloro-3(1-naphthyloxy)propan-2-ol (99% e.e.). Pichia mexicana 11105 resting cells gave 85% yield of (R)-1-chloro-3(1-naphthyloxy)propan-2-ol (precursor of propranolol) (95% e.e). The reduction process is applied to other alpha -haloketones, a lower e.e, being obtained the closer the size of the ketone substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00425-0
• 作为产物：
  描述：

  1-bromo-3-(1-naphthyloxy)-2-propanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以90.2%的产率得到(RS)-1-bromo-3-(1-naphthyloxy)-2-propanol
  参考文献：
  名称：

  一种盐酸普萘洛尔的制备方法

  摘要：

  本发明属于医药化工领域，尤其涉及一种盐酸普萘洛尔的制备方法，包括以下步骤：步骤1：1‑萘酚在氢氧化钠溶液中与1,3‑二溴(碘)丙酮反应，生成1‑溴(碘)‑3‑(1‑萘氧基)‑2‑丙酮；步骤2：1‑溴(碘)‑3‑(1‑萘氧基)‑2‑丙酮在有机溶剂中被硼氢化钠还原，生成1‑溴(碘)‑3‑(1‑萘氧基)‑2‑丙醇；步骤3：1‑溴(碘)‑3‑(1‑萘氧基)‑2‑丙醇在有机溶剂中与异丙胺反应，生成1‑异丙氨基‑3‑(1‑萘氧基)‑2‑丙醇；步骤4：1‑异丙氨基‑3‑(1‑萘氧基)‑2‑丙醇与盐酸成盐，生成盐酸普萘洛尔，该方法避免了环氧氯丙烷的使用，更为安全环保，反应过程中没有含环氧乙烷结构的中间体，用药安全性更高。

  公开号：

  CN108586273B

文献信息

• Antihypertensive ureidopiperidines
  作者：J. L. Archibald、D. R. Beardsley、G. M. F. Bisset、P. Fairbrother、J. L. Jackson、A. Opalko、T. J. Ward

  DOI：10.1021/jm00182a009

  日期：1980.8

  These compounds are related to the benzamidopiperidines exemplified by indoramin. Some of the ureidopiperidines are more potent antihypertensive agents than their benzamidopiperidine counterparts. Two examples, 1-(2-thenoyl)-3-[1-[2-(3-indolyl)ethyl]piperid-4-yl]urea and 1-(2-thenoyl)-3-[1-[4-(4-fluorophenyl)-4-oxobutyl]piperid-4-yl]urea (19 and 58), emerged as the most potent antihypertensive agents

  报道了一系列1-芳烷基-4-脲基哌啶的合成。这些化合物与吲哚胺为例的苯甲酰氨基哌啶有关。一些脲基哌啶比其苯甲酰氨基哌啶具有更强的抗高血压药。两个例子，1-（2-thenoyl）-3- [1- [2-（3-吲哚基）乙基]哌啶-4-基]脲和1-（2-thenoyl）-3- [1- [4- （4-氟苯基）-4-氧代丁基]哌啶-4-基]脲（19和58）成为本系列中最有效的降压药。
• BE640312
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.
• Derivatives of .beta.-adrenergic antagonists: N-nitrosopropranolol and N-hydroxypropranolol and its aldonitrone
  作者：Shoufang Zhang、Mark L. Powell、Wendel L. Nelson、Peter J. Wirth

  DOI：10.1021/jm00357a027

  日期：1983.3

  Potential precursors to chemically reactive species derived from the beta-adrenergic antagonist propranolol were synthesized and tested for mutagenicity in the Ames Salmonella assay. N-Hydroxypropranolol (1), the corresponding aldonitrone, 3-(1-naphthoxy)-2-hydroxypropionaldehyde N-isopropylnitrone (2), and N-nitrosopropranolol (3) were prepared and tested. N-Hydroxypropranolol (1) was obtained by direct alkylation of 3-(1-naphthoxy)-1-bromo-2-propanol with N-isopropylhydroxylamine and isolated as its neutral oxalate or HBr salt. The aldonitrone (2) was obtained by mercuric oxide oxidation of the hydroxylamine. N-Nitrosopropranolol (3) was prepared by treating propranolol with nitrous acid. None of the compounds was mutagenic in the Ames assay with Salmonella typhimurium TA-98 and TA-100 strains, either in the absence or in the presence of the S-9 liver fraction from Arochlor 1254 treated rats. None of the compounds was significantly toxic to the bacteria, except for slight toxicity of the oxalate salt of 1.
• ARCHIBALD J. L.; BEARDSLEY D. R.; BISSET G. M.; FAIRBROTHER P.; JACKSON J+, J. MED. CHEM., 1980, 23, NO 8, 857-861
  作者：ARCHIBALD J. L.、 BEARDSLEY D. R.、 BISSET G. M.、 FAIRBROTHER P.、 JACKSON J+

  DOI：——

  日期：——