2-(2-methoxy-6-methylphenoxy)acetic acid | 38206-99-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-methoxy-6-methylphenoxy)acetic acid
• 英文别名: 2-methoxyl-6-methyl-phenoxyacetic acid
• CAS: 38206-99-4
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: SCGBULDXHWGNBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methoxy-6-methylphenoxy)acetic acid 、 2-(2-苄基氧基苯氧基)乙胺 在 氯甲酸乙酯 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.5h， 以76%的产率得到N-(2-(2-(benzyloxy)phenoxy)ethyl)-2-(2-methoxy-6-methylphenoxy)acetamide
  参考文献：
  名称：

  Structure–activity relationships in 1,4-benzodioxan-related compounds. 10. Novel α1-adrenoreceptor antagonists related to openphendioxan: Synthesis, biological evaluation, and α1d computational study

  摘要：

  A series of novel openphendioxan analogues were synthesized and tested at alpha(1)-adrenoreceptor (AR) subtypes by binding and functional assays. The alpha(1d)-AR binding profile was also examined by means of 2D, 3D-QSAR together with docking studies. Multiple regression analysis suggested the relevance of adequate number of heteroatoms in the whole molecule and of passive membrane diffusion to enhance alpha(1d)-AR affinity. Docking simulations against a computational structural model of the biological target further proved this evidence and furnished support for chemiometric analysis, where polar, electrostatic, hydrophobic and shape effects of the ortho substituents in the phenoxy terminal, most likely governing ligand binding, helped the depiction of pharmacophore hypothesis for the examined ligands data set. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.002
• 作为产物：
  描述：

  ethyl 2-methoxyl-6-methyl-phenoxyacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以4.4 g (90%)的产率得到2-(2-methoxy-6-methylphenoxy)acetic acid
  参考文献：
  名称：

  Retroviral protease inhibiting compounds

  摘要：

  一种化合物的化学式为：##STR1##，被披露为一种逆转录病毒蛋白酶抑制剂化合物。还披露了用于抑制HIV感染的方法和组合物。

  公开号：

  US05905068A1

文献信息

• Synthesis and SAR studies of potent HIV protease inhibitors containing novel dimethylphenoxyl acetates as P 2 ligands
  作者：Xiaoqi Chen、Dale J. Kempf、Lin Li、Hing L. Sham、Sudthida Vasavanonda、Norman E. Wideburg、Ayda Saldivar、Kennan C. Marsh、Edith McDonald、Daniel W. Norbeck

  DOI：10.1016/j.bmcl.2003.08.043

  日期：2003.11

  combination of ligands were investigated. Preliminary pharmacokinetic studies in rats indicated rapid elimination of the inhibitors from the blood, and the plasma levels were not significantly enhanced by coadministration with ritonavir. However, the novel structural features and the high intrinsic antiviral potency of this series provides potential for the future exploration of prodrug strategies.

  异丙基取代的4-thioazolyl缬氨酸侧链是高度优化的P（2）-P（3）配体，用于基于C2对称性的HIV蛋白酶抑制剂，如药物利托那韦的例子。用构象约束的六氢呋喃呋喃基氧基P（2）配体与利托那韦核心二胺另一端的二甲基苯氧基乙酸酯结合，取代侧链，产生了高效的HIV蛋白酶抑制剂。与利托那韦相比，在不存在和存在50％人血清的情况下，MT4细胞中的体外抗病毒活性分别提高了10倍和20倍。研究了抑制剂系列与这种配体组合的构效关系。在大鼠中进行的初步药代动力学研究表明，该抑制剂可从血液中快速清除，与利托那韦合用不会显着提高血浆水平。然而，该系列的新颖结构特征和高内在抗病毒效力为前药策略的未来探索提供了潜力。
• Alpha-hydroxyarylbutanamine inhibitors of aspartyl protease
  申请人：——

  公开号：US20030207934A1

  公开（公告）日：2003-11-06

  Acylated &agr;-hydroxyarylbutanamines and related sulfonamides, ureas and carbamates that inhibit aspartyl protease are disclosed, as are methods of treating diseases, particularly HIV, using these compounds. The compounds have the formula: 1 A representative example is: 2

  本发明公开了一种酰化的α-羟基芳基丁胺和相关的磺酰胺、脲和氨基甲酸酯，它们能够抑制天冬氨酸蛋白酶，同时也公开了使用这些化合物治疗疾病，特别是HIV的方法。这些化合物的化学式为：1，其中一种代表性的示例为：2。
• US5905068A
  申请人：——

  公开号：US5905068A

  公开（公告）日：1999-05-18
• US6696494B2
  申请人：——

  公开号：US6696494B2

  公开（公告）日：2004-02-24
• [EN] alpha -HYDROXYARYLBUTANAMINE INHIBITORS OF ASPARTYL PROTEASE<br/>[FR] INHIBITEURS D'ASPARTYL PROTEASE A BASE DE DOLLAR G(A)-HYDROXYARYLBUTANAMINE
  申请人：ENANTA PHARM INC

  公开号：WO2003034989A2

  公开（公告）日：2003-05-01

  Acylated α-hydroxyarylbutanamines and related sulfonamides, ureas and carbamates that inhibit aspartyl protease are disclosed, as are methods of treating diseases, particularly HIV, using these compounds. The compounds have the formula (I). A representative example is formula (II).