methyl 2-(3-(tert-butyldimethylsilyloxy)benzylamino)acetate

• 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: methyl 2-(3-(tert-butyldimethylsilyloxy)benzylamino)acetate
• 英文别名: 2-(3-(tert-butyldimethylsilyloxy)-benzylamino)acetat；Methyl 2-[[3-[tert-butyl(dimethyl)silyl]oxyphenyl]methylamino]acetate
• 化学式: C₁₆H₂₇NO₃Si
• 分子量: 309.481
• InChiKey: MCTPDJYXXIPKNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-(tert-butyldimethylsilyloxy)benzylamino)acetate 在 盐酸 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 64.0h， 生成 3-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)-1-(3-hydroxybenzyl)imidazolidine-2,4-dione
  参考文献：
  名称：

  Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists

  摘要：

  In humans, bitter taste is mediated by 25 TAS2Rs. Many compounds, including certain active pharmaceutical ingredients, excipients, and nutraceuticals, impart their bitter taste (or in part) through TAS2R8 activation. However, effective TAS2R8 blockers that can either suppress or reduce the bitterness of these compounds have not been described. We are hereby reporting a series of novel 3-(pyrazol-4-yl) imidazolidine-2,4-diones as potent and selective TAS2R8 antagonists. In human sensory tests, S6821 and S7958, two of the most potent analogues from the series, demonstrated efficacy in blocking TAS2R8-mediated bitterness and were selected for development. Following data evaluation by expert panels of a number of national and multinational regulatory bodies, including the US, the EU, and Japan, S6821 and S7958 were approved as safe under conditions of intended use as bitter taste blockers.

  DOI：

  10.1021/acs.jmedchem.0c00388
• 作为产物：
  描述：

  间羟基苯甲醛 在 咪唑 、 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 methyl 2-(3-(tert-butyldimethylsilyloxy)benzylamino)acetate
  参考文献：
  名称：

  Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists

  摘要：

  In humans, bitter taste is mediated by 25 TAS2Rs. Many compounds, including certain active pharmaceutical ingredients, excipients, and nutraceuticals, impart their bitter taste (or in part) through TAS2R8 activation. However, effective TAS2R8 blockers that can either suppress or reduce the bitterness of these compounds have not been described. We are hereby reporting a series of novel 3-(pyrazol-4-yl) imidazolidine-2,4-diones as potent and selective TAS2R8 antagonists. In human sensory tests, S6821 and S7958, two of the most potent analogues from the series, demonstrated efficacy in blocking TAS2R8-mediated bitterness and were selected for development. Following data evaluation by expert panels of a number of national and multinational regulatory bodies, including the US, the EU, and Japan, S6821 and S7958 were approved as safe under conditions of intended use as bitter taste blockers.

  DOI：

  10.1021/acs.jmedchem.0c00388

文献信息

• Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions, and the use thereof in assays to identify compounds that inhibit (block) bitter taste in compositions and use thereof
  申请人：SENOMYX, INC.

  公开号：US09247759B2

  公开（公告）日：2016-02-02

  The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

  本发明涉及发现，T2R味觉受体家族中的特定人类味觉受体对存在于咖啡等物质中的特定苦味化合物产生反应。此外，本发明涉及发现特定化合物和含有该化合物的组合物，其作为苦味阻断剂的功能，以及将其用作苦味阻断剂或调味剂，例如在咖啡和咖啡味食品、饮料和药品中。此外，本发明涉及发现一种对多种不同人类T2R产生拮抗作用的化合物，以及将其用于检测中和作为人类和动物摄入的组合物中的苦味阻断剂。
• [EN] IDENTIFICATION OF HUMAN T2R RECEPTORS AND THE USE THEREOF TO IDENTIFY INHIBITORS (BLOCKERS) OF BITTER TASTE<br/>[FR] IDENTIFICATION DE RÉCEPTEURS T2R HUMAINS ET LEUR UTILISATION POUR IDENTIFIER DES INHIBITEURS (BLOQUEURS) DU GOÛT AMER
  申请人：SENOMYX INC

  公开号：WO2011106114A1

  公开（公告）日：2011-09-01

  The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.
• Discovery and Development of S6821 and S7958 as Potent TAS2R8 Antagonists
  作者：Joseph R. Fotsing、Vincent Darmohusodo、Andrew P. Patron、Brett W. Ching、Thomas Brady、Melissa Arellano、Qing Chen、Timothy J. Davis、Hanghui Liu、Guy Servant、Lan Zhang、Mark Williams、Michael Saganich、Tanya Ditschun、Catherine Tachdjian、Donald S. Karanewsky

  DOI：10.1021/acs.jmedchem.0c00388

  日期：2020.5.14

  In humans, bitter taste is mediated by 25 TAS2Rs. Many compounds, including certain active pharmaceutical ingredients, excipients, and nutraceuticals, impart their bitter taste (or in part) through TAS2R8 activation. However, effective TAS2R8 blockers that can either suppress or reduce the bitterness of these compounds have not been described. We are hereby reporting a series of novel 3-(pyrazol-4-yl) imidazolidine-2,4-diones as potent and selective TAS2R8 antagonists. In human sensory tests, S6821 and S7958, two of the most potent analogues from the series, demonstrated efficacy in blocking TAS2R8-mediated bitterness and were selected for development. Following data evaluation by expert panels of a number of national and multinational regulatory bodies, including the US, the EU, and Japan, S6821 and S7958 were approved as safe under conditions of intended use as bitter taste blockers.