DL-2-(3,4,5-Trihydroxyphenyl)glycin | 86053-99-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: DL-2-(3,4,5-Trihydroxyphenyl)glycin
• 英文别名: (RS)-3,4,5-trihydroxyphenylglycine；(RS)-3,4,5-Thpg；2-amino-2-(3,4,5-trihydroxyphenyl)acetic acid
• CAS: 86053-99-8
• 化学式: C₈H₉NO₅
• 分子量: 199.163
• InChiKey: QQNNBCKCTFTQHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  辛醇 、 DL-2-(3,4,5-Trihydroxyphenyl)glycin 在 氯化亚砜 作用下， 以37%的产率得到Amino-(3,4,5-trihydroxy-phenyl)-acetic acid octyl ester; hydrochloride
  参考文献：
  名称：

  Kobow; Sprung; Schulz, Pharmazie, 1995, vol. 50, # 4, p. 297 - 299

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三羟基苯甲醛 在 盐酸 作用下， 以 水 为溶剂， 生成 DL-2-(3,4,5-Trihydroxyphenyl)glycin
  参考文献：
  名称：

  Structure-activity relationships of new agonists and antagonists of different metabotropic glutamate receptor subtypes

  摘要：

  1 We investigated the agonist and atagonist activities of 22 new phenylglycine and phenylalamine derivatives for metabotropic glutamate receptors (mGluRs) by examining their effects on the signal transduction of mGluR(1), mGluR(2) and mGluR(6) subtypes expressed in Chinese hamster ovary cells. This analysis revealed several structural characteristics that govern receptor subtype specificity of the agonist and antagonist activities of phenylglycine derivatives.2 Hydroxyphenylglycine derivatives possessed either an agonist activity on mGluR(1) mGluR(6) or an antagonist activity on mGluR(1).3 Carboxyphenylglycine derivatives showed an agonist activity on mGluR(2) but an antagonist activity on mGluR(1).4 alpha-Methylation or alpha-ethylation of the carboxyphenylglycine derivatives converts the agonist property For mGluR(2) to an antagonist property, thus producing antagonists at both mGluR(1) and mGluR(2).5 Structurally-corresponding phenylalanine derivatives showed little or no agonist or antagonist activity on any subtypes of the receptors.6 This investigation demonstrates that the nature and positions of side chains and ring substituents incorporated into the phenylglycine structure are critical in determining the agonist and antagonist activities of members of this group of compounds on different subtypes of the mGluR family.7 We also tested two alpha-methyl derivatives of mGluR agonists. (2S, 1'S, 2'S)-2-(2-Carboxycyciopropyl)glycine (L-CCG-I) is a potent agonist for mGluR(2) but alpha-methylation of this compound changes its activity to that of an mGluR(2)-selective antagonist. In contrast, alpha-methylation of L-2-amino-4-phosphonobutyrate (L-AP4) results in retention of an agonist activity on mCluR(6). Thus, alpha-methylation produces different effects, depending on the chemical structures of lead compounds and/or on the subtype of mGluR tested.

  DOI：

  10.1111/j.1476-5381.1996.tb15312.x

文献信息

• WATER SOLUBLE BIOADHESIVES
  申请人：THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO

  公开号：US20220395608A1

  公开（公告）日：2022-12-15

  A water soluble biocompatible adhesive is provided comprising one or more compounds of structure 1 wherein B is an oligomer derived from a polyether or polyalkylene glycol, with a MW<5,000 g/mol, Linker L is a urethane, urea bond, or amide bond; Linker L′ is a urethane or urea bond, A is a chain extender of Mw≤3000 g/mol comprising substituted or unsubstituted alkyl, cycloalkyl and/or aromatic groups, W is a terminal adhesive benzene-1,2-diol derivative or a terminal adhesive benzene-1,2,3-diol derivative, m is 0 or 1; and n is 0, 1, 2, 3 or 4. The compound(s) have a Tg lower than 25° C. The biocompatible adhesive is suitable for use without solvent.
• [EN] AMPHIPHILIC OLIGOMERS AND SELF-ASSEMBLING HYDROGELS FORMED THEREFROM<br/>[FR] OLIGOMÈRES AMPHIPHILES ET HYDROGELS À AUTOASSEMBLAGE FORMÉS À PARTIR DE CEUX-CI
  申请人：[en]THE GOVERNING COUNCIL OF THE UNIVERSITY OF TORONTO

  公开号：WO2022261791A1

  公开（公告）日：2022-12-22

  Amphiphilic oligomers are provided that yield self-assembled, phase-separated hydrogels suitable for sustained release drug delivery. The oligomers are of formula (D-C-A-C)n-B or (D-C-B-C)n-A, where A represents a hydrophilic segment such as polyethylene glycol, B is a degradable hydrophobic segment such as polycaprolactone, C is a linking group comprising a urethane or urea linkage, D is a terminal catechol adhesive group capable of cross- linking, and n is 2 or 3. The oligomers are prepared by (i) reacting either one of a hydrophilic polyol or a hydrophobic polyol with a diisocyanate compound; (ii) reacting the product of step (i) with the other of the hydrophilic polyol and hydrophobic polyol; and (iii) reacting the product of step (ii) with a catechol derivative to form the terminal adhesive groups.