2-(1'-Cyclobutylspiro[3,4-dihydrochromene-2,4'-piperidine]-6-yl)oxyethanol | 1354927-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(1'-Cyclobutylspiro[3,4-dihydrochromene-2,4'-piperidine]-6-yl)oxyethanol
• CAS: 1354927-47-1
• 化学式: C₁₉H₂₇NO₃
• 分子量: 317.428
• InChiKey: ZXCTUMANKFYHJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Tert-butyl 4,6-dihydroxyspiro[chromane-2,4'-piperidine]-1'-carboxylate 在 盐酸 、 三乙基硅烷 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~65.0 ℃ 、310.27 kPa 条件下， 反应 37.0h， 生成 2-(1'-Cyclobutylspiro[3,4-dihydrochromene-2,4'-piperidine]-6-yl)oxyethanol
  参考文献：
  名称：

  Synthesis and evaluation of 4-alkoxy-[1′-cyclobutyl-spiro(3,4-dihydrobenzopyran-2,4′-piperidine)] analogues as histamine-3 receptor antagonists

  摘要：

  A novel class of 4-alkoxy-[1'-cyclobutyl-spiro(3,4-dihydrobenzopyran-2,4'-piperidine)] analogues were designed and synthesized as H3R antagonists. Structure-activity relationship identified sulfone 27 with excellent H3R affinities in both humans and rats, and acceptable pharmacokinetic properties. Further, compound 28 achieved single digit nanomolar H3R affinities in both species with minimum hERG activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.038

文献信息

• Synthesis and evaluation of 4-alkoxy-[1′-cyclobutyl-spiro(3,4-dihydrobenzopyran-2,4′-piperidine)] analogues as histamine-3 receptor antagonists
  作者：Nadine C. Becknell、Reddeppa Reddy Dandu、Jacquelyn A. Lyons、Lisa D. Aimone、Rita Raddatz、Robert L. Hudkins

  DOI：10.1016/j.bmcl.2011.11.038

  日期：2012.1

  A novel class of 4-alkoxy-[1'-cyclobutyl-spiro(3,4-dihydrobenzopyran-2,4'-piperidine)] analogues were designed and synthesized as H3R antagonists. Structure-activity relationship identified sulfone 27 with excellent H3R affinities in both humans and rats, and acceptable pharmacokinetic properties. Further, compound 28 achieved single digit nanomolar H3R affinities in both species with minimum hERG activity. (C) 2011 Elsevier Ltd. All rights reserved.