4-{3-[4-(2-Methyl-imidazol-1-ylmethyl)-phenylsulfanyl]-phenyl}-tetrahydro-pyran-4-carboxylic acid methyl ester | 854750-61-1

• 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: 4-{3-[4-(2-Methyl-imidazol-1-ylmethyl)-phenylsulfanyl]-phenyl}-tetrahydro-pyran-4-carboxylic acid methyl ester
• CAS: 854750-61-1
• 化学式: C₂₄H₂₆N₂O₃S
• 分子量: 422.548
• InChiKey: LVWUZVHBSOYXQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.35
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-{3-[4-(2-Methyl-imidazol-1-ylmethyl)-phenylsulfanyl]-phenyl}-tetrahydro-pyran-4-carboxylic acid methyl ester 在 lithium hydroxide 、 ammonium bicarbonate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 4-[3-[4-(2-Methylimidazol-1-ylmethyl)phenylthio]phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041
• 作为产物：
  描述：

  4-碘苄基溴 在 四(三苯基膦)钯 、 potassium carbonate 、 sodium t-butanolate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 15.0h， 生成 4-{3-[4-(2-Methyl-imidazol-1-ylmethyl)-phenylsulfanyl]-phenyl}-tetrahydro-pyran-4-carboxylic acid methyl ester
  参考文献：
  名称：

  5-Lipoxygenase inhibitors: convenient synthesis of 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-carboxamide analogues

  摘要：

  A convenient synthetic route to 4-[3-(4-heterocyclylphenylthio)phenyl]-3,4,5,6-tetrahydro-2H-pyran-4-earboxamide analogues as 5-LO inhibitors is described. This methodology enabled rapid development of structure-activity relationships (SARs) leading to improvement of pharmacological properties. Thus, new compounds with higher 5-LO inhibitory potency were discovered. The stereo-chemistry requirements of the tetrahydropyran ring are also discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.041