(10-Hydroxymethyl-anthracen-9-ylmethyl)-methyl-carbamic acid tert-butyl ester | 470688-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (10-Hydroxymethyl-anthracen-9-ylmethyl)-methyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[[10-(hydroxymethyl)anthracen-9-yl]methyl]-N-methylcarbamate
• CAS: 470688-81-4
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: FGWLYIGHPXQMEW-UHFFFAOYSA-N

物化性质

• 沸点：
  542.7±29.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (10-Hydroxymethyl-anthracen-9-ylmethyl)-methyl-carbamic acid tert-butyl ester 在 TEA 、 三氧化硫吡啶 、 二甲基亚砜 作用下， 以100%的产率得到(10-Formyl-anthracen-9-ylmethyl)-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Diboronic acids as fluorescent probes for cells expressing sialyl lewis X

  摘要：

  A series of fluorescent diboronic acids was synthesized in nine steps as potential sensors for sialyl Lewis X (sLex). The fluorescent binding studies of these sensors with sLex were carried out in a mixed aqueous solution. Compound 7e was found to show the strongest fluorescence enhancement upon binding with sLex. Using cell cultures, 7e was shown to label sLex-expressing HEPG2 cells at 1 muM, while non-sLex-expressing cells were not labeled. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00339-6
• 作为产物：
  描述：

  10-(Hydroxymethyl)-9-((methylimino)methyl)anthracene 在 sodium tetrahydroborate 、 TEA 作用下， 以 甲醇 为溶剂， 生成 (10-Hydroxymethyl-anthracen-9-ylmethyl)-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Diboronic acids as fluorescent probes for cells expressing sialyl lewis X

  摘要：

  A series of fluorescent diboronic acids was synthesized in nine steps as potential sensors for sialyl Lewis X (sLex). The fluorescent binding studies of these sensors with sLex were carried out in a mixed aqueous solution. Compound 7e was found to show the strongest fluorescence enhancement upon binding with sLex. Using cell cultures, 7e was shown to label sLex-expressing HEPG2 cells at 1 muM, while non-sLex-expressing cells were not labeled. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00339-6

文献信息

• Fluorescent sensor compounds for detecting saccharides
  申请人：North Carolina State University

  公开号：US20040048390A1

  公开（公告）日：2004-03-11

  Fluorescent sensor compounds having the formula: 1 wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl; each m, m′, n, n′, p, and p′ is independently an integer from 0 to 4, inclusive; and each R 1 , R′ 1 , R 2 , R′ 2 , R 3 and R′ 3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol, are useful for the selective detection of saccharides such as glucose and sialyl Lewis X. The compounds find particular use in detecting saccharides in biological samples, and in detecting cancer cells that express cell surface polysaccharides such as sialyl Lewis X.

  具有以下公式的荧光传感器化合物：1其中L选择自烷基，烷基烯，芳基，环烷基，烷氧基，芳氧基，芳基烷基和芳基烷氧基的群；每个m，m'，n，n'，p和p'是独立的整数，范围从0到4，包括0和4；每个R1，R'1，R2，R'2，R3和R'3是独立选择自氢，烷基，烷基烯，芳基，环烷基，烷氧基，芳氧基，芳基烷基，芳基烷氧基，卤素，取代和未取代氨基，以及取代和未取代硫醇的群，可用于选择性检测葡萄糖和唾液酸Lewis X等糖类。该化合物在检测生物样品中的糖类和检测表达细胞表面多糖体如唾液酸Lewis X的癌细胞中具有特殊用途。
• Synthesis and evaluation of aryl boronic acids as fluorescent artificial receptors for biological carbohydrates
  作者：Sandra Craig

  DOI：10.1016/j.bioorg.2011.11.003

  日期：2012.2

  Carbohydrates in various forms play a vital role in numerous critical biological processes. The detection of such saccharides can give insight into the progression of such diseases such as cancer. Boronic acids react with 1,2 and 1,3 diols of saccharides in non-aqueous or basic aqueous media. Herein, we describe the design, synthesis and evaluation of three bisboronic acid fluorescent probes, each having about ten linear steps in its synthesis. Among these compounds that were evaluated, 9b was shown to selectively label HepG2, liver carcinoma cell line within a concentration range of 0.5-10 mu M in comparison to COS-7, a normal fibroblast cell line. (C) 2011 Elsevier Inc. All rights reserved.
• US6916660B2
  申请人：——

  公开号：US6916660B2

  公开（公告）日：2005-07-12
• [EN] FLUORESCENT SENSOR COMPOUNDS FOR DETECTING SACCHARIDES<br/>[FR] COMPOSES DE CAPTEUR FLUORESCENTS POUR LA DETECTION DE SACCHARIDES
  申请人：UNIV NORTH CAROLINA STATE

  公开号：WO2003094926A1

  公开（公告）日：2003-11-20

  Fluorescent sensor compounds having the formula: (1) wherein L is selected from the group consisting of alkyl, alkylene, aryl, cycloalkyl, alkoxy, aryloxy, arylalkyl, and arylalkyloxyl; each m, m', n, n', p, and p' is independently an integer from 0 to 4, inclusive; and each R1, R'1, R2, R'2, R3 and R'3 is independently selected from the group consisting of hydrogen, alkyl, alkylene, aryl, cycloalkyll, alkoxy, aryloxy, arylalkyl, arylalkyloxyl, halo, substituted and unsubstituted amino, and substituted and unsubstituted thiol, are useful for the selective detection of saccharides such as glucose and sialyl Lewis X. The compounds find particular use in detecting saccharides in biological samples, and in detecting cancer cells that express cell surface polysaccharides such as sialyl Lewis X.
• Diboronic acids as fluorescent probes for cells expressing sialyl lewis X
  作者：Wenqian Yang、Shouhai Gao、Xingming Gao、Vishnu Vardhan Reddy Karnati、Weijuan Ni、Binghe Wang、W.Borden Hooks、John Carson、Brent Weston

  DOI：10.1016/s0960-894x(02)00339-6

  日期：2002.8

  A series of fluorescent diboronic acids was synthesized in nine steps as potential sensors for sialyl Lewis X (sLex). The fluorescent binding studies of these sensors with sLex were carried out in a mixed aqueous solution. Compound 7e was found to show the strongest fluorescence enhancement upon binding with sLex. Using cell cultures, 7e was shown to label sLex-expressing HEPG2 cells at 1 muM, while non-sLex-expressing cells were not labeled. (C) 2002 Elsevier Science Ltd. All rights reserved.