2-(((tert-butyldimethylsilyl)oxy)methyl)benzoic acid

• 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: 2-(((tert-butyldimethylsilyl)oxy)methyl)benzoic acid
• 英文别名: Benzoic acid, 2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-；2-[[tert-butyl(dimethyl)silyl]oxymethyl]benzoic acid
• 化学式: C₁₄H₂₂O₃Si
• 分子量: 266.412
• InChiKey: YKOBJCDYCMZFHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(((tert-butyldimethylsilyl)oxy)methyl)benzoic acid 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 tert-butyl(2-isocyanatobenzyloxy)dimethylsilane
  参考文献：
  名称：

  Novel anthracycline-spacer-β-glucuronide, -β-glucoside, and -β-galactoside prodrugs for application in selective chemotherapy

  摘要：

  A series of anthracycline prodrugs containing an immolative spacer was synthesized for application in selective chemotherapy. The prodrugs having the general structure anthracycline-spacer-beta-glycoside were designed to be activated by beta-glucuronidase or beta-galactosidase. Prodrugs with -chloro, bromo or -n-hexyl substituents on the spacer were synthesized as well as prodrugs containing a -beta-glucuronyl, -beta-glucosyl or -beta-galactosyl carbamate specifier. The key step in the synthesis of all prodrugs is the highly beta-diastereoselective addition reaction of the anomeric hydroxyl of a glycosyl donor to a spacer isocyanate resulting in the respective beta-glycosyl carbamate pro-moieties. The resulting protected pro-moieties were coupled to an anthracycline. Prodrugs were evaluated with respect to activation rate by the appropriate enzyme and additionally, their IC50 values were determined. Optimal prodrugs in this study were at least 100- to 200-fold less toxic than their corresponding drug in vitro and were activated to the parent drug in a half-life time of approximately 2 h. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00095-4
• 作为产物：
  描述：

  苯酞 、 叔丁基二甲基氯硅烷 在 potassium hydroxide 、 咪唑 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以32%的产率得到2-(((tert-butyldimethylsilyl)oxy)methyl)benzoic acid
  参考文献：
  名称：

  A cascade reaction based fluorescent probe for rapid and selective fluoride ion detection

  摘要：

  报道了一种基于级联反应的比色和荧光探针，用于选择性氟离子检测。该探针在检测氟离子时表现出快速响应（t1/2 = 2.41分钟）和550倍的荧光增强。示范了该探针在活细胞成像中的应用。

  DOI：

  10.1039/c4cc01665c

文献信息

• MODULATORS OF HEMOGLOBIN
  申请人：Global Blood Therapeutics, Inc.

  公开号：US20200157085A1

  公开（公告）日：2020-05-21

  The present disclosure relates generally to compounds and pharmaceutical compositions suitable as modulators of hemoglobin, and methods for their use in treating disorders mediated by hemoglobin.

  本公开涉及一般与血红蛋白调节剂相关的化合物和药物组合物，以及它们在治疗由血红蛋白介导的疾病中的使用方法。
• Turn-on fluorescent probe designed for fluoride ion sensing in aqueous media
  作者：Arundhati Roy、Tanmoy Saha、Pinaki Talukdar

  DOI：10.1016/j.tetlet.2015.06.086

  日期：2015.8

  A NBD-based probe for selective detection of fluoride ion in aqueous media is reported. The probe was designed by applying rules for water solubility and membrane permeability. The probe functions through the fluoride mediated cascade reaction which was studied by H-1 NMR, HPLC analysis, UV-vis, and fluorescence spectroscopy. The sensing process was marked by a colour change from colourless to yellow, and an intriguing 120-fold turn-on green fluorescence. Application of the probe for selective detection of fluoride was demonstrated by live-cell imaging. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel anthracycline-spacer-β-glucuronide, -β-glucoside, and -β-galactoside prodrugs for application in selective chemotherapy
  作者：Ruben G.G. Leenders、Eric W.P. Damen、Edward J.A. Bijsterveld、Hans W. Scheeren、Pieter H.J. Houba、Ida H. van der Meulen-Muileman、Epie Boven、Hidde J. Haisma

  DOI：10.1016/s0968-0896(99)00095-4

  日期：1999.8

  A series of anthracycline prodrugs containing an immolative spacer was synthesized for application in selective chemotherapy. The prodrugs having the general structure anthracycline-spacer-beta-glycoside were designed to be activated by beta-glucuronidase or beta-galactosidase. Prodrugs with -chloro, bromo or -n-hexyl substituents on the spacer were synthesized as well as prodrugs containing a -beta-glucuronyl, -beta-glucosyl or -beta-galactosyl carbamate specifier. The key step in the synthesis of all prodrugs is the highly beta-diastereoselective addition reaction of the anomeric hydroxyl of a glycosyl donor to a spacer isocyanate resulting in the respective beta-glycosyl carbamate pro-moieties. The resulting protected pro-moieties were coupled to an anthracycline. Prodrugs were evaluated with respect to activation rate by the appropriate enzyme and additionally, their IC50 values were determined. Optimal prodrugs in this study were at least 100- to 200-fold less toxic than their corresponding drug in vitro and were activated to the parent drug in a half-life time of approximately 2 h. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A cascade reaction based fluorescent probe for rapid and selective fluoride ion detection
  作者：Arundhati Roy、Dnyaneshwar Kand、Tanmoy Saha、Pinaki Talukdar

  DOI：10.1039/c4cc01665c

  日期：——

  A cascade reaction-based colorimetric and fluorescent probe for selective fluoride ion detection is reported. The probe displays a fast response (t1/2 = 2.41 min) and 550-fold fluorescence enhancement during sensing of fluoride ions. Application of the probe in live cell imaging is demonstrated.

  报道了一种基于级联反应的比色和荧光探针，用于选择性氟离子检测。该探针在检测氟离子时表现出快速响应（t1/2 = 2.41分钟）和550倍的荧光增强。示范了该探针在活细胞成像中的应用。