2,6-dimethyl-3-methoxyphenylacetonitrile | 91131-93-0

• 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: 2,6-dimethyl-3-methoxyphenylacetonitrile
• 英文别名: 3-Methoxy-2,6-dimethylbenzeneacetonitrile；2-(3-methoxy-2,6-dimethylphenyl)acetonitrile
• CAS: 91131-93-0
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: CTMVZWFCBXPJRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3-methoxyphenylacetonitrile 在 盐酸 、 三溴化硼 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.33h， 生成 3-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-2,4-dimethyl-phenol; hydrobromide
  参考文献：
  名称：

  Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation

  摘要：

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.

  DOI：

  10.1021/jm970513p
• 作为产物：
  描述：

  3-methoxy-2,6-dimethylaniline 在 甲醇 、 sodium tetrahydroborate 、 硫酸 、 四丁基氟化铵 、 叔丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙腈 、 正戊烷 为溶剂， 反应 6.58h， 生成 2,6-dimethyl-3-methoxyphenylacetonitrile
  参考文献：
  名称：

  COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF PREPARING COMPOUNDS AND OF THEIR USE

  摘要：

  Disclosed are compounds and pharmaceutically acceptable salts thereof that may be used in the treatment of subjects in need thereof. The compounds disclosed herein may be inhibitors of tyrosine and threonine-specific cdc2-inhibitory kinase (Myt1). Also disclosed are pharmaceutical compositions containing the compounds or pharmaceutically acceptable salts thereof and methods of their preparation and use.

  公开号：

  US20230122909A1

文献信息

• US3979444A
  申请人：——

  公开号：US3979444A

  公开（公告）日：1976-09-07
• Benzylimidazolines as h5-HT_1B/1D Serotonin Receptor Ligands: A Structure−Affinity Investigation
  作者：Ho Law、Malgorzata Dukat、Milt Teitler、David K. H. Lee、Lucia Mazzocco、Raj Kamboj、Vik Rampersad、Thomas Prisinzano、Richard A. Glennon

  DOI：10.1021/jm970513p

  日期：1998.6.1

  Benzylimidazolines may represent a class of 5-HT1D ligands that has yet to be exploited. On the basis of a previous report that the 2-(substituted-benzyl)imidazoline alpha-adrenergic agonist oxymetazoline (8) binds with high affinity at calf brain 5-HT1D receptors, we explored the structure-affinity relationships of a series of related derivatives. Each of the aromatic substituents was removed and then reinstated in a systematic manner to determine the influence of the individual substituents on binding. It was found that all of the aromatic substituents of 8 act in concert to impart high affinity. However, although the 3-hydroxy group could be removed without significantly reducing affinity for h5-HT1D (i.e., human 5-HT1D alpha) receptors, this modification reduced h5-HT1B (i.e., human 5-HT1D beta) receptor affinity by nearly 50-fold. The 2,6-dimethyl groups also contribute to binding but seem to play a greater role for h5-HT1B binding than h5-HT1D binding.With the appropriate structural modifications, several compounds were identified that display 20- to >100-fold selectivity for h5-HT1D versus h5-HT1B receptors. Preliminary functional data suggest that these compounds behave as agonists. Given that 5-HT1D agonists are currently being explored for their antimigraine action and that activation of h5-HT1B receptors might be associated with cardiovascular side effects, h5-HT1D-selective agents may offer a new lead for the development of therapeutically efficacious agents.
• COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF PREPARING COMPOUNDS AND OF THEIR USE
  申请人：Repare Therapeutics Inc.

  公开号：US20230122909A1

  公开（公告）日：2023-04-20

  Disclosed are compounds and pharmaceutically acceptable salts thereof that may be used in the treatment of subjects in need thereof. The compounds disclosed herein may be inhibitors of tyrosine and threonine-specific cdc2-inhibitory kinase (Myt1). Also disclosed are pharmaceutical compositions containing the compounds or pharmaceutically acceptable salts thereof and methods of their preparation and use.