Dodecyl-(7-nitro-benzo[1,2,5]oxadiazol-4-yl)-amine | 102565-91-3

• 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: Dodecyl-(7-nitro-benzo[1,2,5]oxadiazol-4-yl)-amine
• 英文别名: N-Dodecyl-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine；N-dodecyl-4-nitro-2,1,3-benzoxadiazol-7-amine
• CAS: 102565-91-3
• 化学式: C₁₈H₂₈N₄O₃
• 分子量: 348.445
• InChiKey: VSQQJVDMJHAKEV-UHFFFAOYSA-N

物化性质

• 沸点：
  492.0±55.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  十二烷基伯胺 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 以 乙酸乙酯 为溶剂， 生成 Dodecyl-(7-nitro-benzo[1,2,5]oxadiazol-4-yl)-amine
  参考文献：
  名称：

  Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin.

  摘要：

  研究了量子产率和与牛血清白蛋白（BSA）的结合情况，采用了各种荧光的7-烷基氨基（含有2-12个碳原子）、7-苯基氨基和7-对甲氧基苯基氨基衍生物的4-硝基苯并噁二唑（NBD）。其中，烷基氨基衍生物在乙醇和BSA溶液中均表现出较高的量子产率，且具有较长烷基链的衍生物与BSA有更强的亲和力。特别是C8-C12烷基链的衍生物在研究疏水区域作为荧光探针时可能会很有用。在这些探针与BSA结合的过程中，主要结合常数的对数与侧链长度的增加呈线性关系；推测BSA分子上也存在类似于人血清白蛋白分子上的疏水裂缝。根据Sudlow分类法对7-氨基-NBD衍生物的结合置换进行研究时，几乎没有观察到与II位点药物如布洛芬和氟芬那酸的置换。然而，地西泮（一个II位点药物）的行为与其他II位点药物不同。特别有趣的是，地西泮与其他II位点药物之间的置换行为差异随着烷基氨基-NBD探针侧链长度的增加而增加。

  DOI：

  10.1248/cpb.34.333

文献信息

• In Situ Synthesis of a Supramolecular Hydrogelator at an Oil/Water Interface for Stabilization and Stimuli-Induced Fusion of Microdroplets
  作者：Yuki Nishida、Akiko Tanaka、Shota Yamamoto、Yudai Tominaga、Nobuaki Kunikata、Minoru Mizuhata、Tatsuo Maruyama

  DOI：10.1002/anie.201704731

  日期：2017.8.1

  supramolecular gelator and its instantaneous self‐assembly into nanofibers. We then performed the in situ synthesis of this supramolecular gelator at an oil/water interface to produce nanofibers that covered the surfaces of the oil droplets (nanofiber‐stabilized oil droplets). External stimuli induced fusion of the droplets owing to disassembly of the gelator molecules. Finally, we demonstrated that this stimuli‐induced

  由于其可设计的功能特性，超分子水凝胶有望在各种领域中用作新型软材料。本文中，我们开发了一种超分子水凝胶剂的原位合成方法，该方法可以触发水溶液的凝胶化而无需改变温度。这是通过混合两种前驱物实现的，前驱物诱导了超分子胶凝剂的合成及其瞬时自组装成纳米纤维。然后，我们在油/水界面上进行了这种超分子胶凝剂的原位合成，以产生覆盖油滴（纳米纤维稳定的油滴）表面的纳米纤维。由于凝胶剂分子的分解，外部刺激诱导了液滴的融合。最后，我们证明了这种刺激诱导的液滴融合引发了液滴内部的合成反应。这意味着可以将受限的纳米纤维稳定液滴用作刺激响应的微反应器。
• Chain Length Effect on the Binding of Amphiphiles to Serum Albumin and to POPC Bilayers
  作者：R. M. S. Cardoso、H. A. L. Filipe、F. Gomes、N. D. Moreira、W. L. C. Vaz、M. J. Moreno

  DOI：10.1021/jp105163k

  日期：2010.12.16

  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.
• Binding of fluorescent 7-amino-4-nitrobenzoxadiazole derivatives to bovine serum albumin.
  作者：YASUO MATUSHITA、MASAAKI TAKAHASHI、IKUO MORIGUCHI

  DOI：10.1248/cpb.34.333

  日期：——

  The quantum yield and binding to bovine serum albumin (BSA) were investigated with various fluorescent 7-alkylamino (bearing 2-12 carbon atoms), 7-benzylamino, and 7-p-methoxybenzyl-amino derivatives of 4-nitrobenzoxadiazole (NBD). Among them, alkylamino derivatives gave high quantum yield in both ethanol and BSA solution, and greater affinity to BSA was found with those having a longer alkyl chain. In particular, those with C8-C12 alkyl chains may be useful in research on hydrophobic regions as fluorescent probes. In the binding of these probes to BSA, the logarithm of the primary association constant increased linearly with increase in the length of the side chain; a hydrophobic cleft similar to that on the human serum albumin molecule was suggested to exist also on the BSA molecule. In the investigation of the binding displacement of 7-amino-NBD derivatives based on Sudlow's classification, almost no displacement was observed with site II drugs, ibuprofen and flufenamic acid. However, diazepam (a site II drug) showed different behavior from other site II drugs. It was particularly interesting that the difference of the displacing behavior between diazepam and other site II drugs increases with increase of the side chain length of the alkylamino-NBD probes.

  研究了量子产率和与牛血清白蛋白（BSA）的结合情况，采用了各种荧光的7-烷基氨基（含有2-12个碳原子）、7-苯基氨基和7-对甲氧基苯基氨基衍生物的4-硝基苯并噁二唑（NBD）。其中，烷基氨基衍生物在乙醇和BSA溶液中均表现出较高的量子产率，且具有较长烷基链的衍生物与BSA有更强的亲和力。特别是C8-C12烷基链的衍生物在研究疏水区域作为荧光探针时可能会很有用。在这些探针与BSA结合的过程中，主要结合常数的对数与侧链长度的增加呈线性关系；推测BSA分子上也存在类似于人血清白蛋白分子上的疏水裂缝。根据Sudlow分类法对7-氨基-NBD衍生物的结合置换进行研究时，几乎没有观察到与II位点药物如布洛芬和氟芬那酸的置换。然而，地西泮（一个II位点药物）的行为与其他II位点药物不同。特别有趣的是，地西泮与其他II位点药物之间的置换行为差异随着烷基氨基-NBD探针侧链长度的增加而增加。