(Z)-1-{N-pentyl-N-[6-(N-pentylammoniohexyl)amino]}diazen-1-ium-1,2-diolate | 1027238-95-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (Z)-1-{N-pentyl-N-[6-(N-pentylammoniohexyl)amino]}diazen-1-ium-1,2-diolate
• 英文别名: N-hydroxy-N-[pentyl-[6-(pentylamino)hexyl]amino]nitrous amide
• CAS: 1027238-95-4
• 化学式: C₁₆H₃₆N₄O₂
• 分子量: 316.487
• InChiKey: ZCGWLSWGODEEKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.93
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  己二酰氯 在 lithium aluminium tetrahydride 、 氧化亚氮 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 41.0h， 生成 (Z)-1-{N-pentyl-N-[6-(N-pentylammoniohexyl)amino]}diazen-1-ium-1,2-diolate
  参考文献：
  名称：

  More Lipophilic Dialkyldiamine-Based Diazeniumdiolates:  Synthesis, Characterization, and Application in Preparing Thromboresistant Nitric Oxide Release Polymeric Coatings

  摘要：

  The synthesis, characterization, and biomedical application in preparing more thromboresistant polymeric coatings for a series of lipophilic dialkyldiamine-based diazeniumdiolates are described. Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)-(CH2)(6)(NH2R)-R-divided by, where R = CH3, CH2CH3, (CH2)(2)CH3, (CH2)(3)CH3, (CH2)(4)CH3, (CH2)(5)CH3, and (CH2)(11)CH3, are prepared via reaction of the corresponding diamine with NO. The more lipophilic diazeniumdiolates [e.g., R = (CH2)(3)CH3] can be incorporated into hydrophobic polymeric films (e.g., plasticized PVC), and the resulting materials release NO for extended periods of time upon exposure to PBS buffer. The mechanism of NO release from these films is examined in detail. More stable initial NO release can be achieved by adding lipophilic anionic species (e.g., tetraphenylborate derivative) to the polymeric material to buffer the activity of protons within the organic phase. It is shown that the use of these new lipophilic NO-donors in polymers provides the ability to tailor NO release rates for a variety of medical applications. As an example, polymers doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are employed as coatings for vascular grafts in sheep. The NO release grafts exhibited enhanced performance and had an average 95% thrombus-free surface area compared to 42% for the corresponding control grafts when examined after 21d of implantation.

  DOI：

  10.1021/jm030286t

文献信息

• More Lipophilic Dialkyldiamine-Based Diazeniumdiolates:  Synthesis, Characterization, and Application in Preparing Thromboresistant Nitric Oxide Release Polymeric Coatings
  作者：Melissa M. Batchelor、Sylvie L. Reoma、Paul S. Fleser、Vijay K. Nuthakki、Rose E. Callahan、Charles J. Shanley、Jeffrey K. Politis、Jessica Elmore、Scott I. Merz、Mark E. Meyerhoff

  DOI：10.1021/jm030286t

  日期：2003.11.1

  The synthesis, characterization, and biomedical application in preparing more thromboresistant polymeric coatings for a series of lipophilic dialkyldiamine-based diazeniumdiolates are described. Dialkylhexamethylenediamine diazeniumdiolates of the form RN[N(O)NO](-)-(CH2)(6)(NH2R)-R-divided by, where R = CH3, CH2CH3, (CH2)(2)CH3, (CH2)(3)CH3, (CH2)(4)CH3, (CH2)(5)CH3, and (CH2)(11)CH3, are prepared via reaction of the corresponding diamine with NO. The more lipophilic diazeniumdiolates [e.g., R = (CH2)(3)CH3] can be incorporated into hydrophobic polymeric films (e.g., plasticized PVC), and the resulting materials release NO for extended periods of time upon exposure to PBS buffer. The mechanism of NO release from these films is examined in detail. More stable initial NO release can be achieved by adding lipophilic anionic species (e.g., tetraphenylborate derivative) to the polymeric material to buffer the activity of protons within the organic phase. It is shown that the use of these new lipophilic NO-donors in polymers provides the ability to tailor NO release rates for a variety of medical applications. As an example, polymers doped with N,N'-dibutylhexamethylenediamine diazeniumdiolate and a tetraphenylborate derivative are employed as coatings for vascular grafts in sheep. The NO release grafts exhibited enhanced performance and had an average 95% thrombus-free surface area compared to 42% for the corresponding control grafts when examined after 21d of implantation.