6-(3-Aminopropylamino)hexan-1-ol | 221249-91-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(3-Aminopropylamino)hexan-1-ol
• CAS: 221249-91-8
• 化学式: C₉H₂₂N₂O
• 分子量: 174.286
• InChiKey: MCTXWUZIDLDWFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(3-Aminopropylamino)hexan-1-ol 在 N-甲基吗啉 、 重铬酸吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 1. Structural Modifications of the Hydroxyglycine Moiety

  摘要：

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent currently commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Using the general concept of bioisosteric replacement, variations of the hydroxyglycine central "C" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. By this way, the malonic derivative 13a was discovered as the first example of a new series of potent immunosuppressive agents encompassing a retro-amide bond linked to the hexyl-guanidino moiety. Structure-activity relationships of this series were studied by synthesizing compounds 13g-i and 13k-s. Variation of the "right-amide" of 13a led to the urea 19a and the carbamates 23 and 27a which proved to be equally active as DSG in our GVHD model. Finally 27a was found to be the most potent derivative, being slightly more active than DSG in a heart allotransplantation model in rats. Due to the absence of chiral center in its structure and to its improved chemical stability compared to DSG, 27a was selected as a candidate for clinical evaluation.

  DOI：

  10.1021/jm980431g
• 作为产物：
  描述：

  tert-butyl N-[3-(6-hydroxyhexylamino)propyl]carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 6-(3-Aminopropylamino)hexan-1-ol
  参考文献：
  名称：

  [EN] BIOMIMETIC NANOMATERIALS AND USES THEREOF
  [FR] NANOMATÉRIAUX BIOMIMÉTIQUES ET LEURS UTILISATIONS

  摘要：

  本公开涉及仿生纳米材料、化合物、组合物以及用于传递治疗、诊断或预防剂（例如核酸）的方法。

  公开号：

  WO2019027999A1

文献信息

• STING Agonist-Derived LNP-mRNA Vaccine Enhances Protective Immunity Against SARS-CoV-2
  作者：Yuebao Zhang、Jingyue Yan、Xucheng Hou、Chang Wang、Diana D. Kang、Yonger Xue、Shi Du、Binbin Deng、David W. McComb、Shan-Lu Liu、Yichen Zhong、Yizhou Dong

  DOI：10.1021/acs.nanolett.2c04883

  日期：——

  delivery of messenger RNA (mRNA) COVID-19 vaccines has provided large-scale immune protection to the public. To elicit a robust immune response against SARS-CoV-2 infections, antigens produced by mRNAs encoding SARS-CoV-2 Spike glycoprotein need to be efficiently delivered and presented to antigen-presenting cells such as dendritic cells (DCs). As concurrent innate immune stimulation can facilitate the antigen

  脂质纳米颗粒 (LNP) 介导的信使 RNA (mRNA) COVID-19 疫苗的递送为公众提供了大规模的免疫保护。为了引发针对 SARS-CoV-2 感染的强大免疫反应，编码 SARS-CoV-2 Spike 糖蛋白的 mRNA 产生的抗原需要有效递送并呈递给抗原呈递细胞，例如树突状细胞 (DC)。由于同时进行的先天免疫刺激可以促进抗原呈递过程，因此合成了非核苷酸 STING 激动剂衍生的氨基脂质 (SAL) 库，并将其配制为用于 mRNA 递送的 LNP。 SAL12 脂质纳米粒子 (SAL12-LNP) 被认为最有效地递送编码 SARS-CoV-2 刺突糖蛋白 (S) 的 mRNA，同时激活 DC 中的 STING 通路。通过肌内免疫接种两剂 SAL12 S-LNP 在小鼠体内引发了针对 SARS-CoV-2 的强效中和抗体。
• BIOMIMETIC NANOMATERIALS AND USES THEREOF
  申请人：Ohio State Innovation Foundation

  公开号：US20210069336A1

  公开（公告）日：2021-03-11

  The present disclosure relates to biomimetic nanomaterials, compounds, compositions, and methods for delivery of therapeutic, diagnostic, or prophylactic agents (for example, a nucleic acid).
• Structure−Immunosuppressive Activity Relationships of New Analogues of 15-Deoxyspergualin. 1. Structural Modifications of the Hydroxyglycine Moiety
  作者：Luc Lebreton、Jocelyne Annat、Philippe Derrepas、Patrick Dutartre、Patrice Renaut

  DOI：10.1021/jm980431g

  日期：1999.1.1

  A series of new analogues of 15-deoxyspergualin (DSG), an immunosuppressive agent currently commercialized in Japan, was synthesized and tested in a graft-versus-host disease (GVHD) model in mice. Using the general concept of bioisosteric replacement, variations of the hydroxyglycine central "C" region were made in order to determine its optimum structure in terms of in vivo immunosuppressive activity. By this way, the malonic derivative 13a was discovered as the first example of a new series of potent immunosuppressive agents encompassing a retro-amide bond linked to the hexyl-guanidino moiety. Structure-activity relationships of this series were studied by synthesizing compounds 13g-i and 13k-s. Variation of the "right-amide" of 13a led to the urea 19a and the carbamates 23 and 27a which proved to be equally active as DSG in our GVHD model. Finally 27a was found to be the most potent derivative, being slightly more active than DSG in a heart allotransplantation model in rats. Due to the absence of chiral center in its structure and to its improved chemical stability compared to DSG, 27a was selected as a candidate for clinical evaluation.
• [EN] BIOMIMETIC NANOMATERIALS AND USES THEREOF<br/>[FR] NANOMATÉRIAUX BIOMIMÉTIQUES ET LEURS UTILISATIONS
  申请人：OHIO STATE INNOVATION FOUNDATION

  公开号：WO2019027999A1

  公开（公告）日：2019-02-07

  The present disclosure relates to biomimetic nanomaterials, compounds, compositions, and methods for delivery of therapeutic, diagnostic, or prophylactic agents (for example, a nucleic acid).

  本公开涉及仿生纳米材料、化合物、组合物以及用于传递治疗、诊断或预防剂（例如核酸）的方法。