N-hexyl-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine | 94102-47-3

• 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: N-hexyl-7-nitrobenzo[c][1,2,5]oxadiazol-4-amine
• 英文别名: N-Hexyl-7-nitro-2,1,3-benzoxadiazol-4-amine；N-hexyl-4-nitro-2,1,3-benzoxadiazol-7-amine
• CAS: 94102-47-3
• 化学式: C₁₂H₁₆N₄O₃
• 分子量: 264.284
• InChiKey: WJJMTVWQENMRHK-UHFFFAOYSA-N

物化性质

• 沸点：
  426.0±55.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  正己胺 、 4-氯-7-硝基苯并-2-氧杂-1,3-二唑 以 乙酸乙酯 为溶剂， 生成 N-hexyl-7-nitrobenzo[c][1,2,5]oxadiazol-4-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

• Synthesis and fluorescence properties of environment-sensitive 7-(diethylamino)coumarin derivatives
  作者：Stane Pajk

  DOI：10.1016/j.tetlet.2014.09.019

  日期：2014.10

  By linking 7-(diethylamino)coumarin and different aromatic groups via an oxazole moiety, a small series of new environment-sensitive fluorophores have been synthesized. They display varying degrees of environment-sensitivity, depending on the aromatic group present on the oxazole ring. Additionally, these coumarin-based fluorophores show considerably better photostability compared to the nitrobenzoxadiazole fluorophore, and offer a good starting point for the further development of these fluorophores into environment-sensitive membrane probes or for other applications requiring sensitivity to the environment. (C) 2014 Elsevier Ltd. All rights reserved.
• Unveiling the Triplet State of a 4-Amino-7-Nitrobenzofurazan Derivative in Cyclohexane
  作者：Christopher Sveen、Nicolas Macia、Vanina Zaremberg、Belinda Heyne

  DOI：10.1111/php.12402

  日期：2015.3

  AbstractThe nitrobenzofurazan (NBD) moiety has gained tremendous popularity over the last decades due to its fluorogenic nature. Indeed, upon interaction with aliphatic amines, it generates a stable fluorescent adduct, which has been used for protein and lipid labeling. In fact the 4‐amino substituted NBD belongs to the broad family of intramolecular charge transfer molecules, with the amino group acting as an electron donor upon photoexcitation, and the nitro group as an electron acceptor. Although the singlet excited state of 4‐amino NBD derivatives has been abundantly studied, investigation of its triplet manifold is scarce and even the absence of intersystem crossing for this type of molecules has been suggested. However, intramolecular charge transfer molecules are known to undergo intersystem crossing and high phosphorescence quantum yields have been reported in a nonpolar solvent. In the present paper, we have investigated the photophysical and photochemical properties of N‐hexyl‐7‐nitrobenzo[c][1,2,5]xadiazole‐4‐amine. We have shown the existence of a triplet state for this molecule in cyclohexane via nanosecond laser flash photolysis. Interestingly, deactivation of the triplet state leads to photoproducts formation, which are only present in the absence of oxygen.
• 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.
• [EN] COMPOUND OR SALT THEREOF, NATURAL KILLER T CELL ACTIVATOR, AND PHARMACEUTICAL COMPOSITION<br/>[FR] COMPOSÉ OU SON SEL, ACTIVATEUR DE CELLULES T TUEUSES NATURELLES, ET COMPOSITION PHARMACEUTIQUE<br/>[JA] 化合物又はその塩、ナチュラルキラーＴ細胞活性化剤、及び医薬組成物
  申请人：UNIV KEIO

  公开号：WO2017163808A1

  公开（公告）日：2017-09-28

  本発明の課題は、ナチュラルキラーＴ細胞を活性化できる新規な化合物又はその塩、このような化合物又はその塩を含有するナチュラルキラーＴ細胞活性化剤、及び医薬組成物を提供することである。　本発明の化合物は、以下の式（１）で表される化合物又はその塩である。式（１）中のＲ１における１価の炭化水素基の置換基を除いた炭素数と、Ｘ１における２価の炭化水素基の炭素数との合計炭素数が５～５０であることが好ましい。ナチュラルキラーＴ細胞活性化剤は、上記化合物又はその塩を含有する。医薬組成物は、上記化合物又はその薬理学的に許容される塩を含有する。
• A small-molecule probe to decipher stress-induced ER microenvironments and ER-Golgi communication
  作者：Tanoy Dutta、Barsha Chakraborty、Aditya Nigam、Shilpi Minocha、Apurba Lal Koner

  DOI：10.1039/d4tb00572d

  日期：——

  A small molecule organic fluorophore has been developed to monitor the micropolarity inside endoplasmic reticulum in homeostatic and non-homeostatic conditions and visualize ER to Golgi transport.