4-溴-N-(4-甲氧基苯基)-N-甲基苯磺酰胺 | 1022868-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-溴-N-(4-甲氧基苯基)-N-甲基苯磺酰胺
• 英文名称: 4-bromo-N-(4-methoxyphenyl)-N-methylbenzenesulfonamide
• 英文别名: 4-bromo-benzenesulfonic acid-(N-methyl-p-anisidide)；4-Brom-benzolsulfonsaeure-(N-methyl-p-anisidid)
• CAS: 1022868-47-8
• 化学式: C₁₄H₁₄BrNO₃S
• 分子量: 356.24
• InChiKey: QAFYSJLHVLOFCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲氧基苯硼酸 、 4-溴-N-(4-甲氧基苯基)-N-甲基苯磺酰胺 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 0.33h， 以80%的产率得到3'-methoxy-N-(4-methoxyphenyl)-N-methyl[1,1'-biphenyl]-4-sulfonamide
  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：

  4-溴苯磺酰氯 在 吡啶 、 氢氧化钾 、 乙醚 作用下， 生成 4-溴-N-(4-甲氧基苯基)-N-甲基苯磺酰胺
  参考文献：
  名称：

  Identification of Alkyl Halides: N-Alkyl-p-bromobenzenesulfon-p-anisidides

  摘要：

  DOI：

  10.1021/ja01327a066

文献信息

• Mysyk,D.D.; Burmistrov,S.I., Journal of Organic Chemistry USSR (English Translation), 1967, vol. 3, p. 1621 - 1622
  作者：Mysyk,D.D.、Burmistrov,S.I.

  DOI：——

  日期：——
• Novel N-methylsulfonamide and retro-N-methylsulfonamide derivatives as 17β-hydroxysteroid dehydrogenase type 2 (17β-HSD2) inhibitors with good ADME-related physicochemical parameters
  作者：Enrico Perspicace、Annalaura Giorgio、Angelo Carotti、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2013.08.026

  日期：2013.11

  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.
• Identification of Alkyl Halides: N-Alkyl-p-bromobenzenesulfon-p-anisidides
  作者：H. B. Gillespie

  DOI：10.1021/ja01327a066

  日期：1934.12