UMB108 | 859233-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: UMB108
• 英文别名: 3-hydroxyphenylacetic acid phenethyl ether；(3-Phenethyloxy-phenyl)-acetic acid；2-[3-(2-phenylethoxy)phenyl]acetic acid
• CAS: 859233-66-2
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: OALSRRFAECYMBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  UMB108 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  钴催化芳基乙酸等价物与分子氧的 α-羟基化

  摘要：

  钴催化剂在氧化条件下促进N-吡啶基芳基乙酰胺中的单电子转移过程，形成易于与分子氧反应的 α-碳中心自由基，从而获得扁桃酸衍生物。与已知的苄基羟基化方法相比，该方法能够在与( N-吡啶基)酰胺相邻的苄基位置处进行化学和区域选择性羟基化。条件温和、适用范围广、选择性好、合成实用性广，奠定了该反应的优点。

  DOI：

  10.1021/acs.joc.4c00708
• 作为产物：
  描述：

  3-羟基苯乙酸甲酯 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 UMB108
  参考文献：
  名称：

  Novel, potent, selective, and orally bioavailable human βII-tryptase inhibitors

  摘要：

  The synthesis of novel [1,2,4]oxadiazoles and their structure-activity relationship (SAR) for the inhibition of tryptase and related serine proteases is presented. Elaboration of the P'-side afforded potent, selective, and orally bioavailable tryptase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.088

文献信息

• Synthesis and Aldose Reductase Inhibitory Activities of NovelO-Substituted Hydroxyphenylacetic Acid Derivatives
  作者：Dietmar Rakowitz、Helga Angerer、Barbara Matuszczak

  DOI：10.1002/ardp.200600024

  日期：2006.10

  novel aldose reductase inhibitors, several O‐substituted hydroxyphenylacetic acid derivatives were investigated. The highest inhibitory activity was found for compounds 7b and 7c bearing a cyclohexylmethyl substituent. This result demonstrates that within these series, this moiety is a useful surrogate for the 4‐bromo‐2‐fluorobenzyl residue which can be often found in potent aldose reductase inhibitors

  为了继续我们旨在制备新型醛糖还原酶抑制剂的工作，研究了几种 O 取代的羟基苯乙酸衍生物。发现带有环己基甲基取代基的化合物 7b 和 7c 的抑制活性最高。该结果表明，在这些系列中，该部分是 4-溴-2-氟苄基残基的有用替代物，该残基通常可在有效的醛糖还原酶抑制剂中找到。
• Ethers of 3-hydroxyphenylacetic acid as selective gamma-hydroxybutyric acid receptor ligands
  作者：Weibin Chen、Huifang Wu、R. Jason Hernandez、Ashok K. Mehta、Maharaj K. Ticku、Charles P. France、Andrew Coop

  DOI：10.1016/j.bmcl.2005.05.011

  日期：2005.7

  Gamma-hydroxybutyric acid (GHB) is a drug of abuse, a therapeutic, and purportedly a neurotransmitter with a complex mechanism of action in vivo due to direct actions at GABA(B) as well as GHB receptors and because of its metabolism to GABA. Herein, we describe 3-ethers of 3-hydroxyphenylacetic acid, which have relatively high affinity at GHB sites, no significant affinity at GABA receptors, and would not be expected to be rapidly metabolized to GABAergic ligands. The selectivity of these compounds (UMB108, UMB109, and UMB 119) could prove to be useful for studying the biology of GHB receptors, free from GABAergic effects. (c) 2005 Elsevier Ltd. All rights reserved.
• SUBSTITUTED MONOCYCLIC ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B 4? ANTAGONIST ACTIVITY
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0538416A1

  公开（公告）日：1993-04-28
• EP0538416A4
  申请人：——

  公开号：EP0538416A4

  公开（公告）日：1994-05-18
• Novel, potent, selective, and orally bioavailable human βII-tryptase inhibitors
  作者：David Sperandio、Vincent W.-F. Tai、Julia Lohman、Bernie Hirschbein、Rohan Mendonca、Chang-Sun Lee、Jeffrey R. Spencer、James Janc、Margaret Nguyen、Jerlyn Beltman、Paul Sprengeler、Heleen Scheerens、Tong Lin、Liang Liu、Ashwini Gadre、Alisha Kellogg、Michael J. Green、Mary E. McGrath

  DOI：10.1016/j.bmcl.2006.04.088

  日期：2006.8

  The synthesis of novel [1,2,4]oxadiazoles and their structure-activity relationship (SAR) for the inhibition of tryptase and related serine proteases is presented. Elaboration of the P'-side afforded potent, selective, and orally bioavailable tryptase inhibitors. (c) 2006 Elsevier Ltd. All rights reserved.