ethyl 3,4,5-tribenzyloxybenzoate | 100079-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3,4,5-tribenzyloxybenzoate
• 英文别名: Ethyl 3,4,5-tris(benzyloxy)benzoate；ethyl 3,4,5-tris(phenylmethoxy)benzoate
• CAS: 100079-21-8
• 化学式: C₃₀H₂₈O₅
• 分子量: 468.549
• InChiKey: LPOVBWPBHYTZPB-UHFFFAOYSA-N

物化性质

• 沸点：
  594.3±40.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,4,5-tribenzyloxybenzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以89%的产率得到没食子酸乙酯
  参考文献：
  名称：

  Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (−)-epigallocatechin gallate

  摘要：

  Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.063
• 作为产物：
  描述：

  没食子酸乙酯 、 氯化苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 以55%的产率得到ethyl 3,4,5-tribenzyloxybenzoate
  参考文献：
  名称：

  基于AIE/PET的Zn2+/Al3+荧光探针及其在前列腺癌荧光辅助诊断中的应用

  摘要：

  锌和铝离子广泛存在于自然界和人体中。这些金属离子的紊乱不仅与各种生理病理过程密切相关，而且是许多疾病的重要生物标志物。在此，我们构建了一种新型多功能荧光探针（HL），用于特异性检测Zn 2+ /Al 3+。Zn 2+ /Al 3+的加入触发了探针的荧光增强（λ ex  = 400 nm/385 nm, λ em = 510 nm/450 nm）在水性介质/乙醇中，可能是由于聚集诱导发射 (AIE) 效应和抑制 PET 过程/形成 1:1 化学计量 L-Al 复合物抑制 PET 过程。更重要的是，该探针除对PC3细胞中Zn 2+ /Al 3+进行荧光成像外，还成功应用于前列腺癌血清液体活检中血清Zn 2+水平的测定，证实了其在前列腺癌准确检测中的诊断价值。 .

  DOI：

  10.1016/j.dyepig.2022.110372

文献信息

• 一种锌铝离子识别荧光探针及其制备方法和应用
  申请人：上海交通大学医学院附属瑞金医院

  公开号：CN113402417B

  公开（公告）日：2023-01-03

  本发明提供一种锌铝离子识别荧光探针及其制备方法和应用，荧光探针分子内含有席夫碱结构及三个苄基集团。本发明提供的锌铝离子荧光探针具有双机制、双响应、高灵敏度性和高特异性、不受其他金属离子影响、易被细胞摄取、细胞毒性低等特点。将该探针应用于前列腺癌患者的外周血，可以对血清中的锌含量进行定量检测，为疑似前列腺癌患者的诊断提供宝贵信息。将其与前列腺癌血清PSA检测结合，可以有效提升前列腺癌的诊断准确性，避免血清PSA处于灰度区间内的患者的穿刺诊断需要，进而避免过度诊断和过度治疗的发生。
• An AIE/PET-based fluorescent probe for Zn2+/Al3+ detection and its application in fluorescence-assisted diagnosis for prostate cancer
  作者：Xinmiao Lu、Muyu Wu、Siwen Wang、Jingcan Qin、Peiyong Li

  DOI：10.1016/j.dyepig.2022.110372

  日期：2022.7

  emission (AIE) effect and the inhibited PET process/the formation of 1:1 stoichiometric L-Al complex inhibiting PET process. More importantly, besides fluorescence imaging of Zn2+/Al3+ in PC3 cells, the probe has been applied successfully to determination of serum Zn2+ level in liquid biopsy of serum of prostate cancer confirms its diagnostic value in accurate detection for prostate cancer.

  锌和铝离子广泛存在于自然界和人体中。这些金属离子的紊乱不仅与各种生理病理过程密切相关，而且是许多疾病的重要生物标志物。在此，我们构建了一种新型多功能荧光探针（HL），用于特异性检测Zn 2+ /Al 3+。Zn 2+ /Al 3+的加入触发了探针的荧光增强（λ ex  = 400 nm/385 nm, λ em = 510 nm/450 nm）在水性介质/乙醇中，可能是由于聚集诱导发射 (AIE) 效应和抑制 PET 过程/形成 1:1 化学计量 L-Al 复合物抑制 PET 过程。更重要的是，该探针除对PC3细胞中Zn 2+ /Al 3+进行荧光成像外，还成功应用于前列腺癌血清液体活检中血清Zn 2+水平的测定，证实了其在前列腺癌准确检测中的诊断价值。 .
• OGATA, JOSITAKEH;TANAKA, ISAO;IKEHDA, MAKOTO;XARADA, KOKITI;FUDZIMORI, TO+
  作者：OGATA, JOSITAKEH、TANAKA, ISAO、IKEHDA, MAKOTO、XARADA, KOKITI、FUDZIMORI, TO+

  DOI：——

  日期：——
• Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (−)-epigallocatechin gallate
  作者：Kosuke Dodo、Taro Minato、Tomomi Noguchi-Yachide、Masami Suganuma、Yuichi Hashimoto

  DOI：10.1016/j.bmc.2008.07.063

  日期：2008.9

  Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate and gallamide derivatives and evaluated their antiproliferative effects on human leukemia HL-60 cells. Dodecyl 3,4,5-trihydroxybenzoate (6c) showed the most potent activity, being more potent than EGCG. To clarify the molecular mechanism of the antiproliferative action, we investigated the effects of 6c on various factors. Compound 6c was found to induce apoptosis mediated by endoplasmic reticulum (ER)-stress-related caspase-12. Upregulation of gadd-153, an ER-stress marker protein, was also observed. These results indicate that 6c induced apoptosis via the ER-stress-related pathway. (C) 2008 Elsevier Ltd. All rights reserved.
• Construction of a Cu2+-Responsive NIR Fluorescent Probe and the Preliminary Evaluation of its Multifunctional Application
  作者：Tao Zhang、Huirong Chi、Jingjie Guo、Xinmiao Lu、Guolin Li

  DOI：10.1007/s10895-024-03610-2

  日期：——

  Meanwhile, endogenous Cu2+ was deeply involved in plenty of physiological and pathological processes of human. Cu2+ imbalance was related to multiple diseases. Here we developed a Cu2+-responsive NIR probe HX, which not only demonstrated obvious color change when subjected to Cu2+, but also showed linear-dependent NIR fluorescence emission to Cu2+ concentration for Cu2+ detection and quantification both

  Cu 2+被认为是有毒的，是水和食品中最常见的重金属污染。同时，内源性Cu 2+还深入参与人体的许多生理和病理过程。 Cu 2+失衡与多种疾病有关。在这里，我们开发了一种 Cu 2+响应性近红外探针 HX，它不仅在受到 Cu 2+作用时表现出明显的颜色变化，而且在 Cu 2+检测和定量中都表现出与 Cu 2+浓度线性相关的近红外荧光发射。体外和体内。当HX应用于细胞或活体动物中的Cu 2+成像时，可以可视化细胞内Cu 2+波动和肝脏中Cu 2+积累，以指示背景信号较低的细胞或器官中的铜水平。同时，通过应用HX监测肿瘤中Cu 2+ 的摄取，可以评估铜转运蛋白的功能，以筛选对铂类药物敏感的患者。  图解摘要