2-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide | 1262059-04-0

• 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-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide
• 英文别名: 2-methoxy-5-[(2R)-2-[[(2S,3R)-2-methyl-2,3-dihydro-1,4-benzodioxin-3-yl]methylamino]propyl]benzenesulfonamide
• CAS: 1262059-04-0
• 化学式: C₂₀H₂₆N₂O₅S
• 分子量: 406.503
• InChiKey: QXNTWXQFMCUIBK-BIENJYKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+/-)-cis-3-methyl-2,3-dihydro-1,4-benzodioxin-2-carbaldehyde 、 R-(-)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺 在 盐酸 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 2-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide 、 2-methoxy-5-((2R)-2-cis-{[(3-methyl-2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-amino}propyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and α1-adrenoceptor antagonist activity of tamsulosin analogues

  摘要：

  Tamsulosin (-)-1 is the most utilized alpha(1)-adrenoceptor antagonist in the benign prostatic hyperplasia therapy owing to its uroselective antagonism and capability in relieving both obstructive and irritative lower urinary tract symptoms. Here we report the synthesis and pharmacological study of the homochiral (-)-1 analogues (-)-2-(-)-5, bearing definite modifications in the 2-substituted phenoxyethylamino group in order to evaluate their influence on the affinity profile for alpha(1)-adrenoceptor subtypes. The benzyl analogue (-)-3, displaying a preferential antagonist profile for alpha(1A)-than alpha(1D)-and alpha(1B)-adrenoceptors, and a 12-fold higher potency at alpha(1A)-adrenoceptors with respect to the alpha(1B) subtype, may have improved uroselectivity compared to (-)-1. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.042

文献信息

• Synthesis and α1-adrenoceptor antagonist activity of tamsulosin analogues
  作者：Gianni Sagratini、Piero Angeli、Michela Buccioni、Ugo Gulini、Gabriella Marucci、Carlo Melchiorre、Elena Poggesi、Dario Giardinà

  DOI：10.1016/j.ejmech.2010.09.042

  日期：2010.12

  Tamsulosin (-)-1 is the most utilized alpha(1)-adrenoceptor antagonist in the benign prostatic hyperplasia therapy owing to its uroselective antagonism and capability in relieving both obstructive and irritative lower urinary tract symptoms. Here we report the synthesis and pharmacological study of the homochiral (-)-1 analogues (-)-2-(-)-5, bearing definite modifications in the 2-substituted phenoxyethylamino group in order to evaluate their influence on the affinity profile for alpha(1)-adrenoceptor subtypes. The benzyl analogue (-)-3, displaying a preferential antagonist profile for alpha(1A)-than alpha(1D)-and alpha(1B)-adrenoceptors, and a 12-fold higher potency at alpha(1A)-adrenoceptors with respect to the alpha(1B) subtype, may have improved uroselectivity compared to (-)-1. (C) 2010 Elsevier Masson SAS. All rights reserved.