(+/-)-1-azido-3-bromo-2-propanol

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (+/-)-1-azido-3-bromo-2-propanol
• 英文别名: 1-Azido-3-bromopropan-2-ol
• 化学式: C₃H₆BrN₃O
• 分子量: 180.004
• InChiKey: MATJBGYRKJDRBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-1-azido-3-bromo-2-propanol 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.2h， 生成 glycidyl azide
  参考文献：
  名称：

  Enzymatic dynamic kinetic resolution of epihalohydrins

  摘要：

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.009
• 作为产物：
  描述：

  环氧溴丙烷 在 sodium azide 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 生成 (+/-)-1-azido-3-bromo-2-propanol
  参考文献：
  名称：

  Enzymatic dynamic kinetic resolution of epihalohydrins

  摘要：

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.009

文献信息

• Conjugated antimicrobial agents
  申请人：Technion Research & Development Foundation Limited

  公开号：US09149536B2

  公开（公告）日：2015-10-06

  Provided herein are antimicrobial conjugates of two antibiotic agents, exhibiting improved activity also against resistant bacteria, compared to each of the agents separately or their mixture, and having substantially no resistance emerged thereagainst, as well as processes for preparation the same, compositions containing the same, and uses thereof in medical treatments against pathogenic microorganisms. The disclosed antimicrobial conjugates are composed of aminoglycosides and non-ribosomal active antibiotics. Some of the antimicrobial conjugates are prepared via “click” chemistry.

  本文提供了两种抗生素的抗菌结合物，展现出对抗耐药细菌的改善活性，相比单独使用每种抗生素或它们的混合物，并且基本上没有产生抗性，以及制备这些结合物的过程、含有这些结合物的组合物，以及在医疗治疗中对抗病原微生物的用途。所披露的抗菌结合物由氨基糖苷类和非核糖体活性抗生素组成。其中一些抗菌结合物是通过“click”化学方法制备的。
• Design, Synthesis, and Evaluation of Novel Fluoroquinolone−Aminoglycoside Hybrid Antibiotics
  作者：Varvara Pokrovskaya、Valery Belakhov、Mariana Hainrichson、Sima Yaron、Timor Baasov

  DOI：10.1021/jm900028n

  日期：2009.4.23

  A series of new hybrid structures containing fluoroquinolone (ciprofloxacin) and aminoglycoside (neomycin) antibiotics linked via 1,2,3-triazole moiety were designed and synthesized, and their antibacterial activities were determined against both Gram-negative and Gram-positive bacteria, including resistant strains. The nature of spacers in both the ciprofloxacin and neomycin parts greatly influenced the antibacterial activity. The majority of hybrids was significantly more potent than the parent neomycin and overcame most prevalent types of resistance associated with aminoglycosides. Selected hybrids inhibited bacterial protein synthesis with the potencies similar to or better than that of neomycin and were up to 32-fold more potent inhibitors than ciprofloxacin for the fluoroquinolone targets, DNA gyrase and toposiomerase IV, indicating a balanced dual mode of action. Significant delay of resistance formation was observed in both E. coli and B. subtilis to the treatment with ciprofloxacin-neomycin hybrid in comparison to that of each drug separately or their 1: 1 mixture.
• Enzymatic dynamic kinetic resolution of epihalohydrins
  作者：Jeffrey H Lutje Spelberg、Lixia Tang、Richard M Kellogg、Dick B Janssen

  DOI：10.1016/j.tetasy.2004.02.009

  日期：2004.4

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.