1'-Cyclobutyl-6-(thian-4-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine] | 1174724-61-8

• 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: 1'-Cyclobutyl-6-(thian-4-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine]
• CAS: 1174724-61-8
• 化学式: C₂₂H₃₁NO₂S
• 分子量: 373.56
• InChiKey: XXNVFNZAABJZOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1'-Cyclobutyl-6-(thian-4-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine] 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 以83%的产率得到4-(1'-Cyclobutylspiro[3,4-dihydrochromene-2,4'-piperidine]-6-yl)oxythiane 1,1-dioxide
  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
• 作为产物：
  描述：

  四氢噻喃-4-醇 、 1'-cyclobutyl-6-hydroxy-3,4-dihydrospiro-[2H-benzopyran-2,4'-piperidine] 在 偶氮二甲酸二叔丁酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 以55%的产率得到1'-Cyclobutyl-6-(thian-4-yloxy)spiro[3,4-dihydrochromene-2,4'-piperidine]
  参考文献：
  名称：

  [EN] SUBSTITUTED SPIROCYCLIC PIPERIDINE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS
  [FR] DÉRIVÉS DE PIPÉRIDINE SPIROCYCLIQUE SUBSTITUÉS EN TANT QUE LIGANDS DE RÉCEPTEUR D'HISTAMINE-3 (H3)

  摘要：

  公开号：

  WO2009097567A4

文献信息

• SUBSTITUTED SPIROCYCLIC PIPERIDINE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS
  申请人：Cephalon, Inc.

  公开号：EP2250176B1

  公开（公告）日：2012-08-01
• Substituted Spirocyclic Piperidine Derivatives as Histamine-3 (H3) Receptor Ligands
  申请人：Bacon Edward R.

  公开号：US20110071131A1

  公开（公告）日：2011-03-24

  The present invention provides compounds of Formula (I): their use as H 3 antagonists/inverse agonists, processes for their preparation, and pharmaceuticals compositions thereof.
• US8513232B2
  申请人：——

  公开号：US8513232B2

  公开（公告）日：2013-08-20
• [EN] SUBSTITUTED SPIROCYCLIC PIPERIDINE DERIVATIVES AS HISTAMINE-3 (H3) RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE PIPÉRIDINE SPIROCYCLIQUE SUBSTITUÉS EN TANT QUE LIGANDS DE RÉCEPTEUR D'HISTAMINE-3 (H3)
  申请人：CEPHALON INC

  公开号：WO2009097567A4

  公开（公告）日：2009-10-29
• 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.