α-bromo-4-(3-chloropropoxy)propiophenone | 114604-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-bromo-4-(3-chloropropoxy)propiophenone
• 英文别名: 2-Bromo-4'-(3-chloropropoxy)propiophenone；2-bromo-1-[4-(3-chloropropoxy)phenyl]propan-1-one
• CAS: 114604-75-0
• 化学式: C₁₂H₁₄BrClO₂
• 分子量: 305.599
• InChiKey: KQNUUKRTVDFCPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  α-bromo-4-(3-chloropropoxy)propiophenone 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以65%的产率得到1-[4-(3-Chloro-propoxy)-phenyl]-2-hydroxy-propan-1-one
  参考文献：
  名称：

  Synthesis of (aryloxy)alkylamines. 2. Novel imidazo-fused heterocycles with calcium channel blocking and local anesthetic activity

  摘要：

  A series of imidazo-fused heterocycles substituted with an aryloxy)alkylamine side chain were prepared as modifications to butoprozine (I) and found to possess calcium channel blocking activity similar in potency to that of bepridil in trachea smooth muscle and similar to that of verapamil in nitrendipine binding affinity in rabbit cardiac muscle. Of the various imidazo-fused heterocycles prepared, the imidazo[1,2-a]pyridines were also found to be potent local anesthetic agents. While most compounds in this series were equipotent to lidocaine in our initial screen, compounds 2 and 35 showed local anesthetic activity approximately 100 times more potent than lidocaine in our preliminary assays. These compounds represent a novel structural class of local anesthetic agents, and compound 2 is under further investigation.

  DOI：

  10.1021/jm00119a026
• 作为产物：
  描述：

  1-(p-Propionylphenoxy)-3-chloropropane 在 溴 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 α-bromo-4-(3-chloropropoxy)propiophenone
  参考文献：
  名称：

  （芳氧基）烷基胺的合成。1.具有H + K + -ATPase抑制活性的新型抗分泌剂。

  摘要：

  制备了一系列结构Ⅱ和Ⅲ的杂环（芳氧基）烷基胺，发现它们具有胃的抗分泌活性。在制备的各种取代的噻唑，苯并恶唑和苯并噻唑中，噻唑18，苯并恶唑32和苯并噻唑47在幽门结扎的大鼠模型中表现出与雷尼替丁体内相当的胃抗分泌能力。在分离的兔壁系统中，一系列噻唑，苯并恶唑和苯并噻唑在抑制组胺刺激和dcAMP刺激的氨基[14C]嘌呤摄取方面也表现出与雷尼替丁相似的效价。这些化合物抑制了分离的胃微粒体中的H + K +敏感ATPase。抑制14C摄取与体内抗分泌活性之间存在直接关系，和抑制H + K + -ATPase。更有效的抗分泌化合物18、32和47也是更有效的酶抑制剂。这些数据表明，在这些系列化合物中，负责观察到的体外和体内胃抗分泌活性的机制是抑制H + K +-敏感性ATPase的结果。

  DOI：

  10.1021/jm00117a018

文献信息

• Phenyl-substituted indolizines and tetrahydroindolizines
  申请人：——

  公开号：US20010051632A1

  公开（公告）日：2001-12-13

  The invention features pharmaceutically-active indolizines and tetrahydroindolizines that are each substituted with phenyl, methods of making them, and methods of using them.

  本发明涉及具有药用活性的苯基取代的吲哚啉和四氢吲哚啉，其制备方法和使用方法。
• Novel morpholine ketone analogs as potent histamine H3 receptor inverse agonists with wake activity
  作者：Babu G. Sundar、Thomas R. Bailey、Derek Dunn、Greg A. Hostetler、Sankar Chatterjee、Edward R. Bacon、Christoph Yue、Dominique Schweizer、Lisa D. Aimone、John A. Gruner、Jacquelyn Lyons、Rita Raddatz、Brigitte Lesur

  DOI：10.1016/j.bmcl.2012.01.004

  日期：2012.2

  Structure-activity relationship on a novel ketone class of H3R antagonists/inverse agonists is disclosed. Compound 4 showed excellent target potency, selectivity and brain penetration. Evaluation of antagonist 4 in the rat EEG/EMG model demonstrated robust wake activity thereby establishing preclinical proof of concept. (C) 2012 Elsevier Ltd. All rights reserved.
• PRESS, JEFFERY B.
  作者：PRESS, JEFFERY B.

  DOI：——

  日期：——
• SANFILIPPO, PAULINE J.;URBANSKI, MAUD;PRESS, JEFFERY B.;HAJOS, ZOLTAN G.;+, J. MED. CHEM., 31,(1988) N 9, C. 1778-1785
  作者：SANFILIPPO, PAULINE J.、URBANSKI, MAUD、PRESS, JEFFERY B.、HAJOS, ZOLTAN G.、+

  DOI：——

  日期：——
• SANFILIPPO, PAULINE J.;URBANSKI, MAUD;PRESS, JEFFERY B.;DUBINSKY, BARRY;M+, J. MED. CHEM., 31,(1988) N 11, C. 2201-2227
  作者：SANFILIPPO, PAULINE J.、URBANSKI, MAUD、PRESS, JEFFERY B.、DUBINSKY, BARRY、M+

  DOI：——

  日期：——