7-hydroxy-2-methylquinoline-8-carbonitrile | 1111821-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-hydroxy-2-methylquinoline-8-carbonitrile
• 英文别名: 8-cyano-7-hydroxy-2-methylquinoline
• CAS: 1111821-21-6
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: DYAOELLQLWVWNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-hydroxy-2-methylquinoline-8-carbonitrile 在 4-二甲氨基吡啶 、 selenium(IV) oxide 、 sodium tetrahydroborate 、 乙醇 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 CyHQ-OAc
  参考文献：
  名称：

  用于生物应用的 8-氨基喹啉光笼的合成与表征

  摘要：

  受 8-二甲基氨基喹啉 (8-DMAQ) 笼状发色团的启发，制备了可光裂解的 8-氨基喹啉衍生物，旨在为新型笼式支架提供稳健的合成途径。四步多功能工艺允许轻松引入各种氨基取代基，其总产量可用于放大。新型光笼显示出高光解效率和低荧光，与文献参考化合物（如 8-DMAQ-OAc、BHQ-OAc 和 CyHQ-OAc）相当，证明了探针在解笼应用中的实用性。几种衍生物允许在侧链上进一步功能化，因此可以作为设计更复杂的光响应系统的构建块。

  DOI：

  10.1016/j.tetlet.2023.154587
• 作为产物：
  描述：

  7-(methoxymethoxy)-2-methylquinoline-8-carbonitrile 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到7-hydroxy-2-methylquinoline-8-carbonitrile
  参考文献：
  名称：

  喹啉保护的二烷基苯胺的光重排和含苯胺的生物效应物的光释放。

  摘要：

  通过控制由（8-氰基-7-羟基喹啉-2-基）甲基（CyHQ）可光除去的保护基团促进的光重排反应的结果来实现二烷基苯胺的直接释放。对底物范围进行了研究，以获得结构-活性关系并提出了反应机理。在CyHQ核心的2-甲基位置引入甲基取代基可绕开光重排，并显着提高了苯胺释放效率。我们成功地将该策略应用于米非司酮（RU-486）的光活化，米非司酮是一种抗孕激素药物，也用于诱导斑马鱼中的LexPR基因表达系统和基于pGL-VP嵌合调控子的基因开关调控系统。

  DOI：

  10.1021/acs.joc.9b01031

文献信息

• Photochemical Activation of Tertiary Amines for Applications in Studying Cell Physiology
  作者：Naeem Asad、Davide Deodato、Xin Lan、Magnus B. Widegren、David Lee Phillips、Lili Du、Timothy M. Dore

  DOI：10.1021/jacs.7b06363

  日期：2017.9.13

  linked to the 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting group (PPG) to create photoactivatable forms suitable for use in studying cell physiology. The photoactivation of tamoxifen and 4-hydroxytamoxifen, which can be used to activate Cre recombinase and CRISPR-Cas9 gene editing, demonstrated that highly efficient release of bioactive molecules could be achieved through one- and two-photon

  代表性的叔胺与 8-氰基-7-羟基喹啉基 (CyHQ) 光可去除保护基 (PPG) 相连，以创建适用于研究细胞生理学的光活化形式。他莫昔芬和 4-羟基他莫昔芬的光活化可用于激活 Cre 重组酶和 CRISPR-Cas9 基因编辑，表明可以通过单光子和双光子激发（1PE 和 2PE）实现生物活性分子的高效释放。CyHQ 保护的苯胺经历了光氮-克莱森重排而不是释放胺。时间分辨光谱研究表明，叔胺的光释放速度非常快，发生在 70 ps 时间尺度上 CyHQ 的单线激发态。
• Substituent Effects on the Sensitivity of a Quinoline Photoremovable Protecting Group to One- and Two-Photon Excitation
  作者：M. Jarrett Davis、Christopher H. Kragor、Khalilah G. Reddie、Hunter C. Wilson、Yue Zhu、Timothy M. Dore

  DOI：10.1021/jo802658a

  日期：2009.2.20

  Photoremovable protecting groups that can reveal biologically important functional groups through one- and two-photon excitation (1PE and 2PE, respectively) have promise in regulating physiological function in a temporally and spatially restricted manner. Only a few chromophores have sufficient sensitivity to 2PE suitable for use as “caging groups” in physiology experiments. It would be useful to develop

  可以通过单光子和双光子激发（分别为1PE和2PE）激发出生物学上重要的官能团的可光去除保护基团，有望在时间和空间上限制其生理功能。只有少数生色团对2PE具有足够的敏感性，适合用作生理学实验中的“笼型基团”。建立发色团的结构-性质关系，使具有高双光子解开作用截面（δu的发色团）的发色团将是有用的。）可以设计。8-溴-7-羟基喹啉基生色团（BHQ）通过1PE和2PE释放各种官能团。将溴取代基交换为硝基（NHQ），氰基（CyHQ）或氯（CHQ）或将羟基交换为二甲氨基（DMAQ和DMAQ-Cl）或巯基（TQ）会显着改变喹啉发色团的光化学和光物理性质。CyHQ-OAc对乙酸盐释放的敏感性提高了3倍，而NHQ-OAc对光化学不敏感。量子效率（Q û）的氨基和巯基衍生物比BHQ-OAc低约一个数量级。与BHQ-OAc相比，所有生色团均显示出对2PE的敏感性降低，但CyHQ，DMAQ和DMAQ-Cl生色团
• BHQ-CAGED NUCLEOTIDE PROBES PHOTOLYSABLE BY TWO-PHOTON EXCITATION
  申请人：Dore Timothy M.

  公开号：US20100048502A1

  公开（公告）日：2010-02-25

  The disclosure encompasses caged compounds such as caged nucleoside phosphoesters (caged nucleotides). In an embodiment, the caged nucleotides include compounds corresponding to those described by formula (I) that may be activated by two-photon excitation, and methods of synthesis of such compounds. 8-Bromo-7-hydroxyquinoline-caged ATP was synthesized and examined for its photochemistry as a biologically useful, temporally and spatially controlled ATP-releasing reagent. The combination of two-photon excitation hydrolysis and activation of caged ATP enables methods for finely focusing ATP activation at the sub-cellular level or to a greater depth of activation, thereby providing improved resolution of ATP-dependent processes at the cellular level.

  该披露涵盖了笼状化合物，例如笼状核苷酸磷酸酯（笼状核苷酸）。在一种实施方案中，笼状核苷酸包括与公式（I）描述的化合物相对应的化合物，可以通过双光子激发激活，并提供了这种化合物的合成方法。合成了8-溴-7-羟基喹啉笼状ATP，并对其光化学性质进行了检查，作为一种生物学上有用的、时间和空间可控的ATP释放试剂。双光子激发水解和笼状ATP的激活相结合，可以在亚细胞水平或更深的激活深度上精细地聚焦ATP的激活，从而提供了更好的细胞水平上ATP依赖过程的分辨率。
• BHQ-caged nucleotide probes photolysable by two-photon excitation
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US08173620B2

  公开（公告）日：2012-05-08

  The disclosure encompasses caged compounds such as caged nucleoside phosphoesters (caged nucleotides). In an embodiment, the caged nucleotides include compounds corresponding to those described by formula (I) that may be activated by two-photon excitation, and methods of synthesis of such compounds. 8-Bromo-7-hydroxyquinoline-caged ATP was synthesized and examined for its photochemistry as a biologically useful, temporally and spatially controlled ATP-releasing reagent. The combination of two-photon excitation hydrolysis and activation of caged ATP enables methods for finely focusing ATP activation at the sub-cellular level or to a greater depth of activation, thereby providing improved resolution of ATP-dependent processes at the cellular level.

  该披露涵盖了笼状化合物，例如笼状核苷酸磷酸酯（笼状核苷酸）。在一种实施方式中，笼状核苷酸包括与式（I）所描述的化合物相对应的化合物，可以通过双光子激发激活，并且还涉及这些化合物的合成方法。8-溴-7-羟基喹啉笼状ATP已被合成并检查其光化学作用作为一种生物学上有用的、时间和空间可控的ATP释放试剂。双光子激发水解和激活笼状ATP的组合使得在亚细胞水平或更大深度的ATP激活方法得到了精细聚焦，从而提供了在细胞水平上改进ATP依赖过程的分辨率的方法。
• Photoactivatable Odorants for Chemosensory Research
  作者：Sangram Gore、Kirill Ukhanov、Cyril Herbivo、Naeem Asad、Yuriy V. Bobkov、Jeffrey R. Martens、Timothy M. Dore

  DOI：10.1021/acschembio.0c00541

  日期：2020.9.18

  The chemosensory system of any animal relies on a vast array of detectors tuned to distinct chemical cues. Odorant receptors and the ion channels of the TRP family are all uniquely expressed in olfactory tissues in a species-specific manner. Great effort has been made to characterize the molecular and pharmacological properties of these proteins. Nevertheless, most of the natural ligands are highly hydrophobic molecules that are not amenable to controlled delivery. We sought to develop photoreleasable, biologically inactive odorants that could be delivered to the target receptor or ion channel and effectively activated by a short light pulse. Chemically distinct ligands eugenol, benzaldehyde, 2-phenethylamine, ethanethiol, butane-1-thiol, and 2,2-dimethylethane-l-thiol were modified by covalently attaching the photoremovable protecting group (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ). The CyHQderivatives were shown to release the active odorant upon illumination with 365 and 405 nm light. We characterized their bioactivity by measuring activation of recombinant TRPV1 and TRPA1 ion channels expressed in HEK 293 cells and the electroolfactogram (EOG) response from intact mouse olfactory epithelium (OE). Illumination with 405 nm light was sufficient to robustly activate TRP channels within milliseconds of the light pulse. Photoactivation of channels was superior to activation by conventional bath application of the ligands. Photolysis of the CyHQ-protected odorants efficiently activated an EOG response in a dose-dependent manner with kinetics similar to that evoked by the vaporized odorant amyl acetate (AAc). We conclude that CyHQ-based, photoreleasable odorants can be successfully implemented in chemosensory research.