3-叠氮基-3-甲基-1-丁醇 | 105090-76-4

• 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
• 中文名称: 3-叠氮基-3-甲基-1-丁醇
• 英文名称: 3-azido-3-methyl-1-butanol
• 英文别名: 3-Azido-3-methylbutan-1-ol
• CAS: 105090-76-4
• 化学式: C₅H₁₁N₃O
• 分子量: 129.162
• InChiKey: PRHPDSPWDRBUPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  9
• 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：

  3-叠氮基-3-甲基-1-丁醇 在 重铬酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以91%的产率得到3-azido-3-methylbutanal
  参考文献：
  名称：

  Chemistry of naturally occurring polyamines. 10. Nonmetabolizable derivatives of spermine and spermidine

  摘要：

  DOI：

  10.1021/jo00375a018
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 sodium azide 、 dimethyl sulfide borane 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-叠氮基-3-甲基-1-丁醇
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm991043x

文献信息

• Antimicrobial N-chlorinated compositions
  申请人：Novabay Pharmaceuticals, Inc.

  公开号：US08278482B2

  公开（公告）日：2012-10-02

  The present application relates to N-chlorinated cationic compounds of Formula I or a salt thereof, and associated compositions and methods of use as antimicrobial agents.

  本申请涉及到公式I的N-氯化阳离子化合物或其盐，以及相关的组合物和用作抗微生物剂的方法。
• ANTIMICROBIAL N-CHLORINATED COMPOSITIONS
  申请人：Jain Rakesh K.

  公开号：US20100158818A1

  公开（公告）日：2010-06-24

  The present application relates to N-chlorinated cationic compounds of Formula I or a salt thereof, and associated compositions and methods of use as antimicrobial agents.

  本申请涉及式I的N-氯化阳离子化合物或其盐，以及相关组合物和用作抗微生物剂的方法。
• Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 2. Structural Modifications of the Spermidine Moiety
  作者：Luc Lebreton、Eric Jost、Bertrand Carboni、Jocelyne Annat、Michel Vaultier、Patrick Dutartre、Patrice Renaut

  DOI：10.1021/jm991043x

  日期：1999.11.1

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Various substitutions of the spermidine "D" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. Various positions of methylation were first investigated leading to the discovery of the monomethylated malonic derivative 56h in which the pro-R hydrogen of the methylene a to the primary amine of the spermidine moiety has been replaced by a methyl group. Synthesis of the similarly methylated analogue of the previously reported glycolic derivative LF 08-0299 afforded 60e which demonstrated a powerful activity at a dose as low as 0.3 mg/kg in the GVHD model and was much more potent than DSG in the demanding heart allotransplantation model in rats. The improvement of in vivo activity was supposed to be related to an increase of the metabolic stability of the methylated analogues compared to the parent molecules. Due to its very low active dose, compatible with a subcutaneous administration in humans, and its favorable pharmacological and toxicological profile, 60e was selected as a candidate for clinical evaluation.
• Chemistry of naturally occurring polyamines. 10. Nonmetabolizable derivatives of spermine and spermidine
  作者：Srinivasan Nagarajan、Bruce Ganem

  DOI：10.1021/jo00375a018

  日期：1986.12