2,3-dihydro-benzo[1,4]dioxine-6-sulfonic acid trans-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-amide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2,3-dihydro-benzo[1,4]dioxine-6-sulfonic acid trans-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-amide
• 化学式: C₂₇H₃₃F₃N₂O₅S
• 分子量: 554.631
• InChiKey: PPAIEDLGYFCKEB-MEMLXQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.1
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-N-Boc-氨基环己酮 在 三乙酰氧基硼氢化钠 、 sodium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 2,3-dihydro-benzo[1,4]dioxine-6-sulfonic acid trans-(4-{4-[2-(2,2,2-trifluoro-ethoxy)-phenyl]-piperidin-1-yl}-cyclohexyl)-amide
  参考文献：
  名称：

  (Phenylpiperidinyl)cyclohexylsulfonamides: Development of α1a/1d-selective adrenergic receptor antagonists for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS)

  摘要：

  Although alpha(1), adrenergic receptor blockers can be very effective for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS), their usage is limited by CV-related side-effects that are caused by the subtype non-selective nature of the current drugs. To overcome this problem, it was hypothesized that a alpha(1a/1d) subtype selective antagonist would bring more benefit for the therapy of BPH/LUTS. In developing such selective alpha(1a/1d) ligands, a series of (phenylpiperidinyl)cyclohexylsulfonamides has been synthesized and evaluated for binding to three cloned human alpha(1)-adrenergic receptor subtypes. Many compounds showed equal affinity for both alpha(1a) and alpha(1d) subtypes with good selectivity versus the alpha(1b) subtype. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.098

文献信息

• US7470711B2
  申请人：——

  公开号：US7470711B2

  公开（公告）日：2008-12-30
• (Phenylpiperidinyl)cyclohexylsulfonamides: Development of α1a/1d-selective adrenergic receptor antagonists for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS)
  作者：George Chiu、Shengjian Li、Peter J. Connolly、Virginia Pulito、Jingchun Liu、Steven A. Middleton

  DOI：10.1016/j.bmcl.2007.04.098

  日期：2007.7

  Although alpha(1), adrenergic receptor blockers can be very effective for the treatment of benign prostatic hyperplasia/lower urinary tract symptoms (BPH/LUTS), their usage is limited by CV-related side-effects that are caused by the subtype non-selective nature of the current drugs. To overcome this problem, it was hypothesized that a alpha(1a/1d) subtype selective antagonist would bring more benefit for the therapy of BPH/LUTS. In developing such selective alpha(1a/1d) ligands, a series of (phenylpiperidinyl)cyclohexylsulfonamides has been synthesized and evaluated for binding to three cloned human alpha(1)-adrenergic receptor subtypes. Many compounds showed equal affinity for both alpha(1a) and alpha(1d) subtypes with good selectivity versus the alpha(1b) subtype. (C) 2007 Elsevier Ltd. All rights reserved.