6-methoxy-7-(2-mesyloxyethoxy)indole | 1448661-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-methoxy-7-(2-mesyloxyethoxy)indole
• 英文别名: 2-[(6-methoxy-1H-indol-7-yl)oxy]ethyl methanesulfonate
• CAS: 1448661-52-6
• 化学式: C₁₂H₁₅NO₅S
• 分子量: 285.321
• InChiKey: GHRSEJCWURPONJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-(2-mesyloxyethoxy)indole 在 吡啶 、 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丁醇 、 二甲基亚砜 为溶剂， 反应 35.25h， 生成
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 三氯化硼 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 14.5h， 生成 6-methoxy-7-(2-mesyloxyethoxy)indole
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d

文献信息

• 6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist
  作者：Laura Fumagalli、Marco Pallavicini、Roberta Budriesi、Cristiano Bolchi、Mara Canovi、Alberto Chiarini、Giuseppe Chiodini、Marco Gobbi、Paola Laurino、Matteo Micucci、Valentina Straniero、Ermanno Valoti

  DOI：10.1021/jm400867d

  日期：2013.8.22

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.