N-hydroxy-tridecaneimidamide | 159458-42-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-hydroxy-tridecaneimidamide
• 英文别名: N'-hydroxytridecanimidamide
• CAS: 159458-42-1
• 化学式: C₁₃H₂₈N₂O
• 分子量: 228.378
• InChiKey: CVJFODWFBYEBJK-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±25.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-hydroxy-tridecaneimidamide 、 α-[[(2,4,6-trimethoxyphenyl)amino]carbonyl]benzene acetic acid 以 四氢呋喃 、 溶剂黄146 、 乙酸乙酯 为溶剂， 以11%的产率得到(1)-3-dodecyl-α-phenyl-N-(2,4,6-trimethoxyphenyl)-1,2,4-oxadiazole-5-acetamide
  参考文献：
  名称：

  Isoxazolyl-substituted alkyl amide ACAT inhibitors

  摘要：

  具有ACAT抑制活性的药用化合物的化学式为##STR1##其中n为0、1或2，对于X除了四唑，n=2时R.sub.2 =R.sub.3 =H；R.sub.1为苯基、取代苯基、萘基、取代萘基、杂环芳基或具有1至18个碳原子的碳氢基；R.sub.2和R.sub.3为氢、卤素、羟基、烷基、烯基、环烷基、苯基、取代苯基、杂芳基或形成螺环烷基；X为含有1至4个杂原子的杂单环5元环，所述杂原子为氮、氧或硫，以及它们的组合；R.sub.4为具有1至20个碳原子的碳氢基，同时描述了它们的制备方法。

  公开号：

  US05366987A1
• 作为产物：
  描述：

  氰十二烷 在 盐酸羟胺 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 N-hydroxy-tridecaneimidamide
  参考文献：
  名称：

  杂环酰胺类：酰基辅酶A：胆固醇O-酰基转移酶的抑制剂，在某些物种中具有降胆固醇活性，在兔中具有抗动脉粥样硬化活性。

  摘要：

  合成了一系列杂环酰胺，并将其作为酰基辅酶A抑制剂：胆固醇O-酰基转移酶（ACAT）的体外抑制剂，以及在胆固醇喂养的大鼠中降低胆固醇的方法进行了评估。评价化合物对基于细胞的巨噬细胞ACAT的抑制作用，生物活性和肾上腺毒性。选择候选对象进行胆固醇喂养的狗的评估，并最终评估受伤的胆固醇喂养的兔动脉粥样硬化模型。在急性胆固醇喂养的大鼠模型中，杂环酰胺有效抑制兔肝脏ACAT（IC50 = 0.014-0.11 microM），大多数化合物以3 mg / kg的浓度显着降低血浆胆固醇（42-68％）。在基于细胞的巨噬细胞ACAT分析中评估了大鼠中最有效的化合物的体内生物活性和动脉ACAT抑制作用。两种具有高生物活性的类似物，（+/-）-2-（3-十二烷基异恶唑-5-基）-2-苯基-N-（2,4,6-三甲氧基苯基l）乙酰胺（13a）和（+/-）-2-（5-选择十二烷基异恶唑-3-基）-2-苯基-N-（2

  DOI：

  10.1021/jm9604033

文献信息

• Pyrazolo-substituted alkyl amide acat inhibitors
  申请人：Warner-Lambert Company

  公开号：US05441975A1

  公开（公告）日：1995-08-15

  Pharmaceutically useful compounds having ACAT inhibitory activity of the formula ##STR1## wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R.sub.2 =R.sub.3 =H; R.sub.1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R.sub.2 and R.sub.3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R.sub.4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.

  具有ACAT抑制活性的药用化合物的化学式为##STR1## 其中n为0、1或2，对于X而言，除了四唑，当n=2时，R.sub.2=R.sub.3=H; R.sub.1为苯基、取代苯基、萘基、取代萘基、杂芳基或具有1至18个碳原子的碳氢基；R.sub.2和R.sub.3为氢、卤素、羟基、烷基、烯基、环烷基、苯基、取代苯基、杂芳基或形成螺环烷基；X为含有1至4个杂原子的杂单环5-成员环，所述杂原子为氮、氧或硫，以及它们的组合；R.sub.4为具有1至20个碳原子的碳氢基，同时描述了它们的制造方法。
• Tetrazole alkyl amide acat inhibitors
  申请人：Warner-Lambert Company

  公开号：US05646170A1

  公开（公告）日：1997-07-08

  Pharmaceutically useful compounds having ACAT inhibitory activity of the formula ##STR1## wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R.sub.2 .dbd.R.sub.3 .dbd.H; R.sub.1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R.sub.2 and R.sub.3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R.sub.4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.

  具有ACAT抑制活性的药用化合物的化学式为##STR1## 其中n为0，1或2，对于X而言，除了四唑和n=2时，R.sub.2.dbd.R.sub.3.dbd.H; R.sub.1是苯基，取代苯基，萘基，取代萘基，杂环芳基或具有1至18个碳原子的碳氢基；R.sub.2和R.sub.3是氢，卤素，羟基，烷基，烯基，环烷基，苯基，取代苯基，杂芳基或形成螺环烷基；X是一个杂单环五元环，含有1至4个杂原子，这些杂原子是氮，氧或硫，以及它们的组合；R.sub.4是具有1至20个碳原子的碳氢基。同时还描述了它们的制造方法。
• Heterocyclic-substituted alkyl amide acat inhibitors
  申请人：Warner-Lambert Company

  公开号：US05693657A1

  公开（公告）日：1997-12-02

  Pharmaceutically useful compounds having ACAT inhibitory activity of the formula ##STR1## wherein n is 0, 1, or 2, for X other than tetrazole and n=2 then R.sub.2 .dbd.R.sub.3 .dbd.H; R.sub.1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R.sub.2 and R.sub.3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; X is a heteromonocyclic 5-membered ring containing one to four heteroatoms, said heteroatoms being nitrogen, oxygen or sulfur, and combination thereof; and R.sub.4 is a hydrocarbon group having from one to 20 carbon atoms are described as well as methods of their manufacture.

  具有ACAT抑制活性的药用化合物的化学式为##STR1## 其中n为0、1或2，对于X而言，除了四唑，当n=2时，R.sub.2 =R.sub.3=H；R.sub.1为苯基、取代苯基、萘基、取代萘基、杂环芳基或具有1-18个碳原子的碳氢基；R.sub.2和R.sub.3为氢、卤素、羟基、烷基、烯基、环烷基、苯基、取代苯基、杂芳基或形成螺环烷基；X为含有1-4个杂原子的杂单环5-元环，所述杂原子为氮、氧或硫和其组合；R.sub.4为具有1-20个碳原子的碳氢基。同时还描述了它们的制备方法。
• LONG CHAIN BASE SPHINGOSINE KINASE INHIBITORS
  申请人：UNIVERSITY OF VIRGINIA PATENT FOUNDATION

  公开号：US20150210675A1

  公开（公告）日：2015-07-30

  The invention relates to inhibitors of Sphingosine Kinase enzymatic activity, and methods of treating diseases and disorders by administering inhibitors of Sphingosine Kinase enzymatic activity.

  本发明涉及抑制鞘氨醇激酶酶活性的抑制剂，以及通过给予鞘氨醇激酶酶活性抑制剂治疗疾病和疾患的方法。
• Structure–activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors
  作者：Molly D. Congdon、Elizabeth S. Childress、Neeraj N. Patwardhan、James Gumkowski、Emily A. Morris、Yugesh Kharel、Kevin R. Lynch、Webster L. Santos

  DOI：10.1016/j.bmcl.2015.03.041

  日期：2015.11

  Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1. (C) 2015 Elsevier Ltd. All rights reserved.