4-n-octylamino-7-nitrobenz-2-oxa-1,3-diazole | 94102-48-4

• 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-octylamino-7-nitrobenz-2-oxa-1,3-diazole
• 英文别名: 4-n-Octylamino-7-nitrobenz-2,1,3-oxadiazol；N-octyl-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine；7-nitro-N-octylbenzo-furazan-4-amine；7-nitro-N-octylbenzo[c][1,2,5]oxadiazol-4-amine；4-nitro-N-octyl-2,1,3-benzoxadiazol-7-amine
• CAS: 94102-48-4
• 化学式: C₁₄H₂₀N₄O₃
• 分子量: 292.338
• InChiKey: MMFHWEUQUCUFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  辛胺 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以90%的产率得到4-n-octylamino-7-nitrobenz-2-oxa-1,3-diazole
  参考文献：
  名称：

  表面反应性与消除Kemp的催化纳米棒的自组装之间的互连性

  摘要：

  了解催化过程动力学背后的基本事实是跨学科的长期追求。在本文中，我们报告了具有催化活性的金纳米棒的自组装，可以通过调节其对不同pH值下质子转移反应的反应性来进行调节。与底物诱导的模板化和协同操作性不同，提高的聚集速率是由于仅在反应过程中改变了催化表面电荷，因为反应物（5-硝基苯并恶唑）的带负电过渡态在带正电的E2途径上形成于带正电的纳米棒上。在此，催化过程中扩散性的增强也可以作为另外的贡献因素。此外，

  DOI：

  10.1002/chem.202100450

文献信息

• 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。
• Reversible fluorescence modulation through energy transfer with ABC triblock copolymer micelles as scaffolds
  作者：Jian Chen、Fang Zeng、Shuizhu Wu、Jianqing Zhao、Qiming Chen、Zhen Tong

  DOI：10.1039/b810677k

  日期：——

  The micelle system formed by an amphiphilic triblock copolymer in water serves as a novel scaffold for fluorescence resonance energy transfer as well as light-induced reversible fluorescence modulation for a hydrophobic fluorescent dye.

  一种两亲性三嵌段共聚物在水中形成的胶束系统可作为一种新型支架，用于荧光共振能量转移以及疏水性荧光染料的光诱导可逆荧光调制。
• Transient Metallo‐Lipidoid Assemblies Amplify Covalent Catalysis of Aqueous and Non‐Aqueous Reactions
  作者：Manju Solra、Rohit Kapila、Sourav Das、Preeti Bhatt、Subinoy Rana

  DOI：10.1002/anie.202400348

  日期：2024.4.8

  A transient metallo-lipidoid supramolecular assembly is constructed utilizing a ligand L1 and a tetracoordinate chelating agent NTA-R. The self-assembled vesicular structures upregulate the catalysis of both aqueous and non-aqueous chemical reactions. The metal ions facilitate transient activation of the assembly, thereby enabling temporal control of the catalytic chemical reactions.

  利用配体L1和四配位螯合剂 NTA-R 构建了瞬态金属类脂超分子组装体。自组装的囊泡结构上调水性和非水性化学反应的催化。金属离子促进组件的瞬时激活，从而实现催化化学反应的时间控制。
• 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：——
• 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.