3,4-dihydro-6-(2-thienyl)naphthalen-1(2H)-one | 169192-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3,4-dihydro-6-(2-thienyl)naphthalen-1(2H)-one
• 英文别名: 3,4-Dihydro-6-(2-thienyl)-1(2H)-naphthalenone；3,4-Dihydro-6-(thien-2-yl)-1(2H)-naphthalenone；6-thiophen-2-yl-3,4-dihydro-2H-naphthalen-1-one
• CAS: 169192-58-9
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: SPJQUTMWLJNXRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-6-(2-thienyl)naphthalen-1(2H)-one 在 sodium azide 作用下， 以 甲烷磺酸 、 二氯甲烷 为溶剂， 以35%的产率得到2,3,4,5-tetrahydro-7-(2-thienyl)benzo[c]azepin-1-one
  参考文献：
  名称：

  Aromatic ring functionalization of benzolactam derivatives: New potent dopamine D3 receptor ligands

  摘要：

  Since the discovery of the dopamine D-3 receptor, an intensive effort has been directed toward the development of potent and selective ligands in order to elucidate the function and potential therapeutic advantages of targeting D-3 receptors. As a part of our efforts, a novel series of substituted benzolactams derivatives was synthesized mostly through palladium-catalyzed reactions. Their affinities on D-1-D-4 receptors were evaluated and the data led us to highly potent D-3 ligands, some of them highly selective for D-3 receptor, compared to the related dopamine receptor subtypes. Functional D-3 activity assays of the most relevant compounds have been carried out revealing antagonist as well as partial agonist activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.083
• 作为产物：
  描述：

  6-羟基-1-四氢萘酮 在 吡啶 、 四丁基溴化铵 、 palladium diacetate 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 2.5h， 生成 3,4-dihydro-6-(2-thienyl)naphthalen-1(2H)-one
  参考文献：
  名称：

  Aromatic ring functionalization of benzolactam derivatives: New potent dopamine D3 receptor ligands

  摘要：

  Since the discovery of the dopamine D-3 receptor, an intensive effort has been directed toward the development of potent and selective ligands in order to elucidate the function and potential therapeutic advantages of targeting D-3 receptors. As a part of our efforts, a novel series of substituted benzolactams derivatives was synthesized mostly through palladium-catalyzed reactions. Their affinities on D-1-D-4 receptors were evaluated and the data led us to highly potent D-3 ligands, some of them highly selective for D-3 receptor, compared to the related dopamine receptor subtypes. Functional D-3 activity assays of the most relevant compounds have been carried out revealing antagonist as well as partial agonist activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.083

文献信息

• Tetracyclic compound
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US05646283A1

  公开（公告）日：1997-07-08

  This invention relates to a novel tetracyclic compound represented by formula (I): ##STR1## or its pharmacologically-acceptable salt. The compound of this invention has strong immunosuppressive activity, and is useful as an immunosuppressive agent and as an agent for treating autoimmune disease.

  本发明涉及一种新型四环化合物，其化学式为(I): ##STR1## 或其药学上可接受的盐。该化合物具有强烈的免疫抑制活性，可作为免疫抑制剂和治疗自身免疫性疾病的药物。
• NOVEL TETRACYCLIC COMPOUND
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0721942A1

  公开（公告）日：1996-07-17

  A novel tetracyclic compound represented by general formula (I) or a pharmacologically acceptable salt thereof. It has a potent immunosuppressive activity and is useful as an immunosuppressant and a remedy for autoimmune diseases.

  一种由通式（I）代表的新型四环化合物或其药理学上可接受的盐。 它具有强效的免疫抑制活性，可用作免疫抑制剂和自身免疫性疾病的治疗药物。
• TETRACYCLIC COMPOUND
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP0721942B1

  公开（公告）日：2002-06-05
• US5646283A
  申请人：——

  公开号：US5646283A

  公开（公告）日：1997-07-08
• Aromatic ring functionalization of benzolactam derivatives: New potent dopamine D3 receptor ligands
  作者：Raquel Ortega、Harald Hübner、Peter Gmeiner、Christian F. Masaguer

  DOI：10.1016/j.bmcl.2010.12.083

  日期：2011.5

  Since the discovery of the dopamine D-3 receptor, an intensive effort has been directed toward the development of potent and selective ligands in order to elucidate the function and potential therapeutic advantages of targeting D-3 receptors. As a part of our efforts, a novel series of substituted benzolactams derivatives was synthesized mostly through palladium-catalyzed reactions. Their affinities on D-1-D-4 receptors were evaluated and the data led us to highly potent D-3 ligands, some of them highly selective for D-3 receptor, compared to the related dopamine receptor subtypes. Functional D-3 activity assays of the most relevant compounds have been carried out revealing antagonist as well as partial agonist activity. (C) 2010 Elsevier Ltd. All rights reserved.