N-(4-bromophenyl)-3-methoxy-N-methylbenzenesulfonamide | 1492050-28-8

• 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: N-(4-bromophenyl)-3-methoxy-N-methylbenzenesulfonamide
• CAS: 1492050-28-8
• 化学式: C₁₄H₁₄BrNO₃S
• 分子量: 356.24
• InChiKey: WRYQOMDVVFZOIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-3-methoxy-N-methylbenzenesulfonamide 在 四(三苯基膦)钯 、 三氟二甲基硫醚络合物 、 caesium carbonate 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.33h， 生成 3-hydroxy-N-(3'-hydroxy[1,1'-biphenyl]-4-yl)-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors with good ADME-related physicochemical parameters

  摘要：

  Under physiological conditions healthy bones are maintained by a well tightened balance between osteoclast (OCs) and osteoblast (OBs) activity. Disruption of this balance leads to osteoporosis characterized by decline in bone function and skeletal rigidity. Inhibition of 17 beta-hydroxysteroid dehydrogenase type 2 (17 beta-HSD2) could help maintaining the appropriate bone mass density by increasing the level of estradiol and testosterone in bone. Herein, we described the synthesis, the physicochemical properties and the biological evaluation of novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17 beta-HSD2 inhibitors showing high potency (compound 10f, IC50 = 23 n M), with a good selectivity toward 17 beta-HSD1 (the isoenzyme responsible of the reverse reaction), and a likely good in vitro ADME profile. It was also shown that the acidity of the phenolic hydroxy correlates with the inhibitory potency, suggesting pKa as a predictive parameter for the activity of this class of inhibitors. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.026
• 作为产物：
  描述：

  3-甲氧基苯磺酰氯 、 4-溴-N-甲基苯胺 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到N-(4-bromophenyl)-3-methoxy-N-methylbenzenesulfonamide
  参考文献：
  名称：

  Potent 11β-Hydroxylase Inhibitors with Inverse Metabolic Stability in Human Plasma and Hepatic S9 Fractions To Promote Wound Healing

  摘要：

  Topical application of CYP11B1 inhibitors to reduce cutaneous cortisol is a novel strategy to promote healing of chronic wounds. Pyridyl substituted arylsulfonyltetrahydroquinolines were designed and synthesized resulting in a strong inhibitor 34 (IC50 = S nM). It showed no inhibition of CYP17 and CYP19 and no mutagenic effects. It exhibited inverse metabolic stability in plasma (t(1/2) >> 150 mm), which is similar to wound fluid in composition, and in liver S9 fractions (t(1/2) = 16 mm).

  DOI：

  10.1021/jm501004t