1-(2,3-二甲基苯氧基)-3-(甲基氨基)-2-丙醇 | 802287-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(2,3-二甲基苯氧基)-3-(甲基氨基)-2-丙醇
• 中文别名: 2-(1-乙基戊基)-1,3-二噁戊环-4-甲醇
• 英文名称: 1-(2,3-dimethyl-phenoxy)-3-methylamino-propan-2-ol
• 英文别名: 1-(2,3-dimethylphenoxy)-3-methylaminopropan-2-ol；1-(2,3-Dimethylphenoxy)-3-(methylamino)propan-2-ol
• CAS: 802287-59-8
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: AJXANSSMVBQVSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,3-二甲基苯氧基)-3-(甲基氨基)-2-丙醇 、 N,N'-羰基二咪唑 在 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 5-(2,3-dimethylphenoxymethyl)-3-methyloxazolidin-2-one
  参考文献：
  名称：

  WO2008/51763

  摘要：

  公开号：
• 作为产物：
  描述：

  二甲酚 在 potassium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 14.0h， 生成 1-(2,3-二甲基苯氧基)-3-(甲基氨基)-2-丙醇
  参考文献：
  名称：

  Bicyclic carbamates as inhibitors of papain-like cathepsin proteases

  摘要：

  A 6-oxa-1-aza-bicyclo[3.2.1]octan-7-one system inhibits the proteolytic activity of several cysteine proteases belonging to the papain family. In vitro mechanistic studies and in silico calculations suggest that the minimal pi-overlap between the bridgehead nitrogen and the carbonyl leads to a considerable weakening of the urethane system, making it susceptible to nucleophilic attack from the active site thiol group. The resulting covalent adduct is slowly hydrolyzed, releasing the hydroxypiperidine product of the inhibitor. Synthesis and testing of a set of analogs led to variable protease subtype selectivities ranging from micromolar to nanomolar potencies. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.014

文献信息

• WO2008/51763
  申请人：——

  公开号：——

  公开（公告）日：——
• CATHEPSIN PROTEASES INHIBITORS
  申请人：IRM LLC

  公开号：EP2078027A1

  公开（公告）日：2009-07-15
• [EN] CATHEPSIN PROTEASES INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉASES DE TYPE CATHEPSINES
  申请人：IRM LLC

  公开号：WO2008051763A1

  公开（公告）日：2008-05-02

  [EN] The invention provides compounds (I) and pharmaceutical compositions thereof, and more particularly, bicyclic carbamates, which are useful as cathepsin inhibitors, and methods for using such compounds or pharmaceutically acceptable salts thereof, wherein X is 0 or S; R¹ is OR², halo, (CR₂)_nR³, nitro, cyano, amino, aniido, sulfonamide, or an optionally substituted C_1-6 alkyl, C_2-6 alkenyl, or C_3-6 alkynyl;R² is H, (CR²)nR³, or an optionally substituted C_1-6alkyl, C_2-6 alkenyl or C_3-6 alkynyl; R³ is an optionally substituted aryl, heteroaryl, carbocyciic ring or heterocyclic ring; m is 1-3; and n is 0-4.
  [FR] L'invention concerne des composés (I) et des compositions pharmaceutiques de ceux-ci et plus particulièrement des carbamates bicycliques, lesquels sont utiles en tant qu'inhibiteurs des cathepsines ; et des procédés d'utilisation de tels composés ou de sels acceptables du point de vue pharmaceutique de ceux-ci. [Dans la formule (I), X est O ou S ; R¹ est OR², un halogéno, (CR²)_nR³, un nitro, un cyano, un amino, un amido, un sulfonamide ou un alkyle en C_1-6, alcényle en C_2-6 ou alcynyle en C_3-6 éventuellement substitué ; R² est H, (CR²)_nR³ ou un alkyle en C_1-6, alcényle en C_2-6 ou alcynyle en C_3-6 éventuellement substitué ; R³ est un aryle, hétéroaryle, cycle carbocyclique ou hétérocycle éventuellement substitué; m vaut 1-3 ; et n vaut 0-4.]
• Bicyclic carbamates as inhibitors of papain-like cathepsin proteases
  作者：Robert Epple、Hugo D. Urbina、Ross Russo、Hong Liu、Daniel Mason、Badry Bursulaya、Christine Tumanut、Jun Li、Jennifer L. Harris

  DOI：10.1016/j.bmcl.2006.12.014

  日期：2007.3

  A 6-oxa-1-aza-bicyclo[3.2.1]octan-7-one system inhibits the proteolytic activity of several cysteine proteases belonging to the papain family. In vitro mechanistic studies and in silico calculations suggest that the minimal pi-overlap between the bridgehead nitrogen and the carbonyl leads to a considerable weakening of the urethane system, making it susceptible to nucleophilic attack from the active site thiol group. The resulting covalent adduct is slowly hydrolyzed, releasing the hydroxypiperidine product of the inhibitor. Synthesis and testing of a set of analogs led to variable protease subtype selectivities ranging from micromolar to nanomolar potencies. (c) 2006 Elsevier Ltd. All rights reserved.