7-nitro-N-propylbenzo[c][1,2,5]oxadiazol-4-amine | 54517-98-5

• 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: 7-nitro-N-propylbenzo[c][1,2,5]oxadiazol-4-amine
• 英文别名: (7-nitrobenzo[1,2,5]oxadiazol-4-yl)propylamine；7-propylamine-4-nitrobenzo[c][1,2,5]oxadiazole；4-propylamino-7-nitrobenzo-2-oxa-1,3-diazole；7-nitro-N-propyl-2,1,3-benzoxadiazol-4-amine；4-propylamino-7-nitro-2,1,3-benzoxadiazole；4-n-propylamino-7-nitrobenzofurazan；4-Benzofurazanamine, 7-nitro-N-propyl-；4-nitro-N-propyl-2,1,3-benzoxadiazol-7-amine
• CAS: 54517-98-5
• 化学式: C₉H₁₀N₄O₃
• mdl: MFCD12188532
• 分子量: 222.203
• InChiKey: YVWDSXHBXWTADD-UHFFFAOYSA-N

物化性质

• 熔点：
  110-112 °C
• 沸点：
  398.7±52.0 °C(Predicted)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-nitro-N-propylbenzo[c][1,2,5]oxadiazol-4-amine 、 氯甲酸烯丙酯 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以88%的产率得到4-allyl (propyl)carbamate-7-nitro-2,1,3-benzoxadiazole
  参考文献：
  名称：

  比色和荧光开启探针，用于一氧化碳和活细胞成像

  摘要：

  设计并合成了用于CO的比色和荧光双探针。该探针能够通过比色测定法在无色到黄色磷酸盐缓冲液中用比色法灵敏和特异性地检测CO，在480 nm激发时，其荧光开启强度增强了75倍，检测极限为26.3 nM。该探针显示出巨大的潜力，可在不干扰活细胞成像的情况下感应细胞内CO。另一方面，该探针还可以被肉眼用作空气中一氧化碳气体的高效便捷的视觉指示器。

  DOI：

  10.1016/j.tetlet.2016.05.073
• 作为产物：
  描述：

  正丙胺 、 4-氯-7-硝基-1-苯并呋喃 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以94%的产率得到7-nitro-N-propylbenzo[c][1,2,5]oxadiazol-4-amine
  参考文献：
  名称：

  Norbornane-based cationic antimicrobial peptidomimetics targeting the bacterial membrane

  摘要：

  The design, synthesis and evaluation of a small series of potent amphiphilic norbornane antibacterial agents has been performed (compound 10 MIC = 0.25 mu g/mL against MRSA). Molecular modelling indicates rapid aggregation of this class of antibacterial agent prior to membrane association and insertion. Two fluorescent analogues (compound 29 with 4-amino-naphthalimide and 34 with 4-nitrobenz-2-oxal,3-diazole fluorophores) with good activity (MIC = 0.5 mu g/mL against MRSA) were also constructed and confocal microscopy studies indicate that the primary site of interaction for this family of compounds is the bacterial membrane. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.09.072

文献信息

• Glycoconjugated Site-Selective DNA-Methylating Agent Targeting Glucose Transporters on Glioma Cells
  作者：Mairin K. Buchanan、Chase N. Needham、Nina E. Neill、Maria C. White、Charles B. Kelly、Kelly Mastro-Kishton、Lacie M. Chauvigne-Hines、Tyler J. Goodwin、Andrew L. McIver、Libero J. Bartolotti、Arthur R. Frampton、Andrea J. Bourdelais、Sridhar Varadarajan

  DOI：10.1021/acs.biochem.6b01075

  日期：2017.1.17

  selective uptake via glucose transporters, which are overexpressed in most cancers. The design features of the molecule, its synthesis, its reactivity with DNA, and its toxicity in human glioblastoma cells are reported here. In this molecule, a glucosamine unit, which can facilitate uptake via glucose transporters, is conjugated to one end of a bispyrrole triamide unit, which is known to bind to the

  脱氧核糖核酸烷基化药物继续仍然是抵抗癌症的武器库中的重要武器。然而，由于它们引起的不加区别的DNA损伤以及它们不能特异性地靶向癌细胞，它们通常遭受若干缺点。我们已经开发出一种策略，通过设计一种可以靶向癌细胞的位点特异性DNA甲基化剂来克服当前DNA烷基化化疗药物的不足，因为它可以通过葡萄糖转运蛋白选择性地摄取，而葡萄糖转运蛋白在大多数癌症中都是过表达的。本文报道了该分子的设计特征，其合成，与DNA的反应性及其在人胶质母细胞瘤细胞中的毒性。在该分子中，可通过葡萄糖转运蛋白促进摄取的葡萄糖胺单元与双吡咯三酰胺单元的一端偶联，已知它会在富含A / T的区域与DNA的小沟结合。磺酸甲酯部分被束缚在双吡咯单元的另一端，以用作DNA甲基化剂。该分子与DNA反应后仅产生N3-甲基腺嘌呤加合物，并且对抗治疗的人成胶质细胞瘤细胞的毒性要比食品和药物管理局批准的糖化DNA甲基化药物链霉菌素高。使用我们分子的荧
• Surface modification of silica nanoparticles: a new strategy for the realization of self-organized fluorescence chemosensors
  作者：Enrico Rampazzo、Elena Brasola、Silvia Marcuz、Fabrizio Mancin、Paolo Tecilla、Umberto Tonellato

  DOI：10.1039/b502052b

  日期：——

  The self-organization of the proper subunits of a fluorescence chemosensor on the surface of silica nanoparticles allows the easy design and realization of new effective sensing systems. Commercially available silica particles (20 nm diameter) were functionalized with triethoxysilane derivatives of selective Cu(II) ligands and fluorescent dyes. Grafting of the sensor components to the particle surface ensures the spatial proximity between the sensor components and, as a consequence, binding of Cu(II) ions by the ligand subunits leads to quenching of the fluorescent units emission. In 9 : 1 DMSO–water solution, the coated silica nanoparticles (CSNs) selectively detect copper ions down to nanomolar concentrations. The operative range of the sensors can be tuned either by switching the ligand units or by modification of the components ratio. Sensors with the desired photophysical properties can be easily prepared by using different fluorescent dyes. Moreover, the organization of the network of sensor components gives rise to cooperative and collective effects: on one hand, the ligand subunits bound to the particle surfaces cooperate to form multivalent binding sites with an increased affinity for the Cu(II) ions; on the other hand, binding of a single metal ion leads to the quenching of several fluorescent groups producing a remarkable signal amplification.

  二氧化硅纳米颗粒表面上荧光化学传感器的适当亚基的自组装使得易于设计和实现新的有效传感系统。商业可获得的二氧化硅颗粒（20nm直径）通过三乙氧基硅烷衍生的选择性Cu(II)配体和荧光染料进行功能化。将传感器组件嫁接到颗粒表面上确保传感器组件之间的空间接近，因此，配体亚基结合Cu(II)离子导致荧光单元的荧光发射熄灭。在9：1 DMSO-水溶液中，涂层的二氧化硅纳米颗粒（CSNs）能够选择性地检测铜离子，检测极限达到纳摩尔浓度。传感器的操作范围可以通过切换配体单元或通过改变组件比例来进行调节。通过使用不同的荧光染料，可以很容易地制备具有所需光物理性质的传感器。此外，传感器组件的网络组织导致协同和集体效应：一方面，连接在颗粒表面上的配体亚基协作形成具有增加的亲和力的多价结合位点用于Cu(II)离子；另一方面，单个金属离子的结合导致几个荧光基团的熄灭，产生显著的信号增强。
• 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。
• A fast-response fluorescent probe for hypochlorous acid detection and its application in exogenous and endogenous HOCl imaging of living cells
  作者：Yin Jiang、Guansheng Zheng、Ning Cai、Huatang Zhang、Yi Tan、Mengjiao Huang、Yonghe He、Jun He、Hongyan Sun

  DOI：10.1039/c7cc07373a

  日期：——

  A facile fluorescent probe (NBD-DOP) has been developed to detect hypochlorous acid (HOCl) in this study. The probe consists of a NBD fluorophore and a dopamine moiety that reacts with HOCl specifically. The dopamine group quenches the fluorescence of NBD efficiently through a photoinduced electron transfer (PET) effect. Experimental data showed that NBD-DOP could detect HOCl with ultrafast response

  在这项研究中，已经开发出一种简便的荧光探针（NBD-DOP）来检测次氯酸（HOCl）。该探针由NBD荧光团和与HOCl特异性反应的多巴胺部分组成。多巴胺基团通过光致电子转移（PET）效应有效地淬灭NBD的荧光。实验数据表明，NBD-DOP可以在宽pH范围内以超快响应，高灵敏度和高选择性检测HOCl。该探针还可以用于检测产生HOC1的髓过氧化物酶。此外，NBD-DOP已通过共聚焦荧光显微镜技术应用于活细胞中外源性和内源性HOCl的成像。
• 一种CO探针及其制备方法和应用
  申请人：华南理工大学

  公开号：CN105622540B

  公开（公告）日：2017-10-20

  本发明属于检测材料技术领域，公开了一种CO探针及其制备方法和应用。所述CO探针具有式(I)所示的结构式。所述制备方法为：将氯代对硝基苯并呋咱加入到正丙胺有机溶液中，然后加入无水碳酸钾，室温搅拌反应，反应产物经分离纯化，得到4‑丙胺基‑7‑硝基‑2,1,3‑苯并氧杂噁二唑；将4‑丙胺基‑7‑硝基‑2,1,3‑苯并氧杂噁二唑溶解到无水有机溶剂中，惰性气氛保护下加入二异丙基乙胺搅拌混合均匀，然后滴加入氯甲酸烯丙酯，室温反应，反应产物经分离纯化，得到所述CO探针。本发明的制备方法过程简单，易于操作；所得CO探针具有紫外和荧光双响应，可用于CO检测领域。