4-n-Hexadecylamino-7-nitrobenz-2,1,3-oxadiazol | 101237-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-n-Hexadecylamino-7-nitrobenz-2,1,3-oxadiazol
• 英文别名: N-Hexadecyl-7-nitro-2,1,3-benzoxadiazol-4-amine；N-hexadecyl-4-nitro-2,1,3-benzoxadiazol-7-amine
• CAS: 101237-16-5
• 化学式: C₂₂H₃₆N₄O₃
• 分子量: 404.553
• InChiKey: LUFVRSBIQWUQBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  十六胺 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 sodium carbonate 作用下， 以 氯仿 为溶剂， 以20%的产率得到4-n-Hexadecylamino-7-nitrobenz-2,1,3-oxadiazol
  参考文献：
  名称：

  Chain Length Effect on the Binding of Amphiphiles to Serum Albumin and to POPC Bilayers

  摘要：

  The interaction of small molecules, such as drugs or metabolites, with proteins and biomembranes is of fundamental importance for their bioavailability. The systematic characterization of the binding affinity for structurally related ligands may provide rules that allow its prediction for any other relevant molecule. In this work we have studied a homologous series of fluorescent fatty amines with the fluorescent moiety 7-nitrobenz-2-oxa-1,3-diazol-4-yl covalently bound to the amine group (NBD-C-n; n = 4, 6, 8, 10, 12, 14, and 16) in aqueous solution and associated with BSA or lipid bilayers. We have found a linear dependence with the length of the alkyl chain, up to NBD-C-10, for the Gibb's free energy of partition between the aqueous solution and 1-palmitoyl-2-oleoyl phosphatidylcholine bilayers equal to Delta Delta G = 2.5 +/- 0.3 kJ/mol per methylene group. Additionally, the amphiphiles interacted efficiently with bovine serum albumin, and it was inhibited by fatty acids indicating that binding occurs to the fatty acids highest affinity binding site. The association of the amphiphiles with BSA and POPC bilayers was performed at different temperatures (15-35 degrees C) allowing for the calculation of the enthalpic and entropic contributions. A value of Delta H = -15 +/- 4 kJ/mol was obtained for all amphiphiles and binding agents. The entropy contribution was always positive and increased with the length of the alkyl chain. The location of the ligand in the biological membrane is also of high relevance, namely because this will determine its effect on biomembrane properties at high ligand concentrations. With this goal, we have measured some photophysical properties of the amphiphiles inserted in POPC bilayers, and we found no significant variation along the series, indicating that the NBD group is located in a region with similar properties regardless of the length of the nonpolar group. An exception was noted for the case of NBD-C-14 whose parameters were somewhat different from the trend observed.

  DOI：

  10.1021/jp105163k

文献信息

• Heberer, H.; Kersting, H.; Matschiner, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 3, p. 487 - 504
  作者：Heberer, H.、Kersting, H.、Matschiner, H.

  DOI：——

  日期：——
• HEBERER, H.;KERSTING, H.;MATSCHINER, H., J. PRAKT. CHEM., 1985, 327, N 3, 487-504
  作者：HEBERER, H.、KERSTING, H.、MATSCHINER, H.

  DOI：——

  日期：——
• COLOR-CHANGING FISHING EQUIPMENT
  申请人：Pure Fishing, Inc.

  公开号：EP1758447A2

  公开（公告）日：2007-03-07
• EP1758447A4
  申请人：——

  公开号：EP1758447A4

  公开（公告）日：2008-06-04
• Color-changing fishing equipment
  申请人：Cook B. Roger

  公开号：US20050274055A1

  公开（公告）日：2005-12-15

  Fishing equipment incorporates one or more dyes that change or display colors upon exposure to light (photochromic), a change in temperature (thermochromic), or change in ambient moisture (solvatochromic). Products that include parts that are made of, or products which are wholly a polymer can benefit from the present invention and may include fishing lines, fishing rods, fishing reels, thread used to wrap line guides on a fishing rod, and fishing reel handles.