5-methacrylamido-2-hydroxymethylphenylboronic acid | 244178-19-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-methacrylamido-2-hydroxymethylphenylboronic acid
• 英文别名: N-(1-hydroxy-3H-2,1-benzoxaborol-6-yl)-2-methylprop-2-enamide
• CAS: 244178-19-6
• 化学式: C₁₁H₁₂BNO₃
• 分子量: 217.032
• InChiKey: YJZIMDDIKMFPLG-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  频哪醇 、 5-methacrylamido-2-hydroxymethylphenylboronic acid 在 硝基苯 作用下， 以 甲苯 为溶剂， 以90%的产率得到N-(4-(hydroxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methacrylamide
  参考文献：
  名称：

  Molecular imprinting of fructose using a polymerizable benzoboroxole: Effective complexation at pH 7.4

  摘要：

  Covalent molecularly imprinted polymers against D-fructose employing 5-methacrylamido-2-hydroxymethylphenylboronic acid as functional monomer and trimethylpropane trimethacrylate (TRIM) as the crosslinking agent were prepared by a conventional radical bulk polymerization (MIP-BX(Fru)). Batch binding studies for fructose in aqueous buffers containing 10% methanol revealed that the binding capability of MIP-BX(Fru) is paramount compared to a MIP prepared with vinylphenylboronic acid MIP-BA(Fru). Especially, at the biological important pH-value of 7.4 the rebinding of fructose to the MIP-BX(Fru) is with 60 nmol per mg polymer about 3.2 higher compared to the MIP-BA(Fru). A pinacol imprinted polymer was also investigated and showed in case of MIP-BX still an imprinting of 1.7 at pH 7.4 whereas MIP-BA did not show a difference. Cross-reactivity studies at pH 7.4 show the shape-selectivity of the MIP-BX(Fru) in the order of L-fructose, sorbitol, glucose and sucrose. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.04.002
• 作为产物：
  描述：

  5-氨基-2-羟甲基苯硼酸盐酸盐 、 甲基丙烯酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以82%的产率得到5-methacrylamido-2-hydroxymethylphenylboronic acid
  参考文献：
  名称：

  Molecular imprinting of fructose using a polymerizable benzoboroxole: Effective complexation at pH 7.4

  摘要：

  Covalent molecularly imprinted polymers against D-fructose employing 5-methacrylamido-2-hydroxymethylphenylboronic acid as functional monomer and trimethylpropane trimethacrylate (TRIM) as the crosslinking agent were prepared by a conventional radical bulk polymerization (MIP-BX(Fru)). Batch binding studies for fructose in aqueous buffers containing 10% methanol revealed that the binding capability of MIP-BX(Fru) is paramount compared to a MIP prepared with vinylphenylboronic acid MIP-BA(Fru). Especially, at the biological important pH-value of 7.4 the rebinding of fructose to the MIP-BX(Fru) is with 60 nmol per mg polymer about 3.2 higher compared to the MIP-BA(Fru). A pinacol imprinted polymer was also investigated and showed in case of MIP-BX still an imprinting of 1.7 at pH 7.4 whereas MIP-BA did not show a difference. Cross-reactivity studies at pH 7.4 show the shape-selectivity of the MIP-BX(Fru) in the order of L-fructose, sorbitol, glucose and sucrose. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2011.04.002

文献信息

• First steps towards conformationally selective artificial lectins: the chair-boat discrimination by molecularly imprinted polymers
  作者：Vincent Lemau de Talancé、Olivier Massinon、Rachid Baati、Alain Wagner、Stéphane P. Vincent

  DOI：10.1039/c2cc35386e

  日期：——

  A series of molecularly imprinted polymers (MIPs) were prepared in the presence of a synthetic galactoside locked in a 1,4B boat conformation. This study demonstrates that, depending on the polymerisation technique, an organic material can selectively bind a carbohydrate in a biologically relevant boat conformation.

  在合成半乳糖苷以 1,4B 舟形构象锁定的情况下，制备了一系列分子印迹聚合物（MIPs）。这项研究表明，根据聚合技术的不同，有机材料可以选择性地结合具有生物相关舟构象的碳水化合物。
• Multivalent Benzoboroxole Functionalized Polymers as gp120 Glycan Targeted Microbicide Entry Inhibitors
  作者：Julie I. Jay、Bonnie E. Lai、David G. Myszka、Alamelu Mahalingam、Kris Langheinrich、David F. Katz、Patrick F. Kiser

  DOI：10.1021/mp900159n

  日期：2010.2.1

  Microbicides are women-controlled prophylactics for sexually transmitted infections. The most important class of microbicides target HIV-1 and contain antiviral agents formulated for topical vaginal delivery. Identification of new viral entry inhibitors that target the HIV-1 envelope is important because they can inactivate HIV-1 in the vaginal lumen before virions can come in contact with CD4+ cells in the vaginal mucosa. Carbohydrate binding agents (CBAs) demonstrate the ability to act as entry inhibitors due to their ability to bind to glycans and prevent gp120 binding to CD4+ cells. However, as proteins they present significant challenges in regard to economical production and formulation for resource-poor environments. We have synthesized water-soluble polymer CBAs that contain multiple benzoboroxole moieties. A benzoboroxole-functionalized monomer was synthesized and incorporated into linear oligomers with 2-hydroxypropylmethacrylamide (HPMAm) at different feed ratios using free radical polymerization. The benzoboroxole small molecule analogue demonstrated weak affinity for HIV-1BaL gp120 by SPR; however, the 25 mol % functionalized benzoboroxole oligomer demonstrated a 10-fold decrease in the K-D for gp120, suggesting an increased avidity for the multivalent polymer construct. High molecular weight polymers functionalized with 25, 50, and 75 mol % benzoboroxole were synthesized and tested for their ability to neutralize HIV-1 entry for two HIV-1 clades and both R5 and X4 coreceptor tropism. All three polymers demonstrated activity against all viral strains tested with EC(50)s that decrease from 15000 nM (1500 mu g mL(-1)) for the 25 mol % functionalized polymers to 11 nM (11 mu g mL(-1)) for the 75 mol % benzoboroxole-functionalized polymers. These polymers exhibited minimal cytotoxicity after 24 h exposure to a human vaginal cell line.