4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)amino)-4-oxobutanoic acid | 126545-08-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)amino)-4-oxobutanoic acid
• 英文别名: 4-[(1-hydroxy-3H-2,1-benzoxaborol-6-yl)amino]-4-oxobutanoic acid
• CAS: 126545-08-2
• 化学式: C₁₁H₁₂BNO₅
• 分子量: 249.031
• InChiKey: HNAXNQJRMHCJDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)amino)-4-oxobutanoic acid 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-1-(2-aminoethyl)-N4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-il)succinamide
  参考文献：
  名称：

  高灵敏度的荧光探针，用于成像近红外区域中活细胞中的糖蛋白和粘蛋白活性

  摘要：

  据报道，一种新型的荧光分子探针能够在生物活性窗口内以高灵敏度，开启响应以及较大的斯托克斯位移（> 130 nm）检测糖蛋白，特别是粘蛋白。该探针包含一个氨基三聚氰胺作为荧光报告分子，并带有一个连接的苯并环硼氧烷作为识别单元，该受体通过受体的硼半酸酯残基与顺式之间的动态共价反应进行工作。分析物的二醇。通过在Calu-3细胞中存在的粘蛋白标记，可以显示出探针的优越选择性。新的苯并硼恶唑荧光衍生物集聚了关键特性，使其成为高度评价的分子探针：特异性，在水中的出色溶解性以及近红外发射。预期该探针将是对细胞内粘蛋白进行成像以评估粘液相关疾病的绝佳工具，以及对糖基化结构的传感策略，该方法在生物样品中具有治疗学方法的巨大潜力。

  DOI：

  10.1002/chem.201800790
• 作为产物：
  描述：

  2-(羟甲基)苯硼酸环状单酯 在 palladium 10% on activated carbon 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -45.0~60.0 ℃ 、275.8 kPa 条件下， 反应 8.34h， 生成 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  高灵敏度的荧光探针，用于成像近红外区域中活细胞中的糖蛋白和粘蛋白活性

  摘要：

  据报道，一种新型的荧光分子探针能够在生物活性窗口内以高灵敏度，开启响应以及较大的斯托克斯位移（> 130 nm）检测糖蛋白，特别是粘蛋白。该探针包含一个氨基三聚氰胺作为荧光报告分子，并带有一个连接的苯并环硼氧烷作为识别单元，该受体通过受体的硼半酸酯残基与顺式之间的动态共价反应进行工作。分析物的二醇。通过在Calu-3细胞中存在的粘蛋白标记，可以显示出探针的优越选择性。新的苯并硼恶唑荧光衍生物集聚了关键特性，使其成为高度评价的分子探针：特异性，在水中的出色溶解性以及近红外发射。预期该探针将是对细胞内粘蛋白进行成像以评估粘液相关疾病的绝佳工具，以及对糖基化结构的传感策略，该方法在生物样品中具有治疗学方法的巨大潜力。

  DOI：

  10.1002/chem.201800790

文献信息

• Arylboronic Acids. IV. Reactions of Boronophthalide¹
  作者：W. J. Lennarz、H. R. Snyder

  DOI：10.1021/ja01494a021

  日期：1960.5

  The preparation of derivatives of boronophthalide is reported. The product of nitration of boronophthalide, 5-nitroboronophthalide, is reduced to 5- aminoboronophthalide. 5-Aminoboronophthalide is converted to Nsuccinyl-5- aminoboronophthalide and to boronophthalide5-diazonium chloride. Finally, the diazonium compound is coupled with 3-carboxy-2-naphthol. Several attempted transformations of the boronolactone

  报道了硼苯酞衍生物的制备。硼苯酞硝化的产物，5-硝基硼苯酞，被还原为5-氨基硼苯酞。5-氨基硼苯酞转化为Nsuccinyl-5-氨基硼苯酞和硼苯酞5-重氮氯化物。最后，重氮化合物与 3-羧基-2-萘酚偶联。讨论了硼苯酞的硼酸内酯环的几种尝试转化。
• Benzoxaboroles as dynamic covalent receptors for bioconjugation and transport of nucleosides and related drugs: Proof of action in HeLa cells
  作者：Cecilia Samaniego Lopez、Jimena H. Martínez、Sofía L. Acebedo、Carla C. Spagnuolo

  DOI：10.1016/j.bioorg.2019.103059

  日期：2019.9

  In this work we describe not previously explored binding studies on the reversible interaction of benzoxaborole with ligands of medical and pharmaceutical interest such as nucleosidic drugs gemcitabine and capecitabine, as well as the hydrophobic chemotherapeutic doxorubicin. We include functional derivatives of benzoxaborole such as a near infrared fluorescent boronolectine, Cy-Bx, The dynamic covalent interaction in physiological conditions was assessed by spectroscopic techniques yielding moderate to high binding affinities. The cytotoxic activity of the drugs upon conjugation to the boronolectins was evaluated revealing significant influence of the bioconjugation status on the cellular viability. The availability of the conjugate for cellular uptake and localization in the model cancer cell line HeLa was assessed by fluorescence imaging. Benzoxaborole and the fluorescent boronolectin Cy-Bx, proved to be versatile conjugation tools for 1,2 and 1,3-diol containing pharmacophores as well as bioisosteric forms such as 1,2-hydroxyamino, envisioning these small boronolectins as components in systems for drug release with tracking capability.
• Synthesis and evaluation of functionalized benzoboroxoles as potential anti-tuberculosis agents
  作者：Mohammad A. Alam、Kriti Arora、Shirisha Gurrapu、Sravan K. Jonnalagadda、Grady L. Nelson、Paul Kiprof、Subash C. Jonnalagadda、Venkatram R. Mereddy

  DOI：10.1016/j.tet.2016.03.038

  日期：2016.6

  Several derivatives of aminobenzoboroxole have been prepared starting from 2-boronobenzaldehyde. All of these derivatives have been evaluated for their anti-mycobacterial activity on Mycobacterium smegmatis and cytotoxicity on breast cancer cell line MCF7. Based on these studies, all the tested molecules have been found to be generally non-toxic and benzoboroxoles with unsubstituted (primary) amines have been found to exhibit good anti-mycobacterial activity. Some of the key compounds have been evaluated for their anti-tubercular activity on Mycobacterium tuberculosis H37Rv using 7H9 and GAST media. 7-Bromo-6-aminobenzoboroxole 4 has been identified as the lead candidate compound for further development. (C) 2016 Elsevier Ltd. All rights reserved.
• A Highly Sensitive Fluorogenic Probe for Imaging Glycoproteins and Mucine Activity in Live Cells in the Near-Infrared Region
  作者：Cecilia Samaniego Lopez、Jimena Hebe Martínez、María Laura Uhrig、Federico Coluccio Leskow、Carla Cecilia Spagnuolo

  DOI：10.1002/chem.201800790

  日期：2018.4.25

  analyte. The superior selectivity of the probe is displayed by the labeling of mucins present in Calu‐3 cells. The new benzoboroxole fluorescent derivative gathers together key properties to make it a highly rated molecular probe: specificity, excellent solubility in water, and off–on near infrared emission. This probe is expected to be an excellent tool for imaging intracellular mucin to evaluate mucus‐related

  据报道，一种新型的荧光分子探针能够在生物活性窗口内以高灵敏度，开启响应以及较大的斯托克斯位移（> 130 nm）检测糖蛋白，特别是粘蛋白。该探针包含一个氨基三聚氰胺作为荧光报告分子，并带有一个连接的苯并环硼氧烷作为识别单元，该受体通过受体的硼半酸酯残基与顺式之间的动态共价反应进行工作。分析物的二醇。通过在Calu-3细胞中存在的粘蛋白标记，可以显示出探针的优越选择性。新的苯并硼恶唑荧光衍生物集聚了关键特性，使其成为高度评价的分子探针：特异性，在水中的出色溶解性以及近红外发射。预期该探针将是对细胞内粘蛋白进行成像以评估粘液相关疾病的绝佳工具，以及对糖基化结构的传感策略，该方法在生物样品中具有治疗学方法的巨大潜力。