8-Bromo-10,11-dihydrodibenzothiepin-10-on | 13420-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 英文名称: 8-Bromo-10,11-dihydrodibenzothiepin-10-on
• 英文别名: 8-bromodibenzo[b,f]thiepin-10(11H)-one；8-bromo-11H-dibenzo[b,f]thiepin-10-one；8-bromo-10,11-dihydro-dibenz[b.f]thiepin-10-one；3-bromo-6H-benzo[b][1]benzothiepin-5-one
• CAS: 13420-88-7
• 化学式: C₁₄H₉BrOS
• 分子量: 305.195
• InChiKey: OSQAFEGAAZRJSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 8-Bromo-10,11-dihydrodibenzothiepin-10-on 在 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到1-(8-bromodibenzo-[b,f]thiepin-10-yl)-4-methylpiperazine
  参考文献：
  名称：

  Exploring the Neuroleptic Substituent in Octoclothepin: Potential Ligands for Positron Emission Tomography with Subnanomolar Affinity for α₁-Adrenoceptors

  摘要：

  A series of 1-(10.11-dihydrodthenzo[b,f]thiepin-(10-y-l)-4-methylpiperazine analogues substituted in the 8-position of the 10,11-dihydrodibenzo[b,f]thiepine scaffold with aryl, heteroaryl. amine, and amide substituents are described. The compounds were: designed using the previously reported Liljefors-Bogeso pharmacophore model for dopamine 1)2 and alpha(1)-adrenocetor antagonists. with the aim of obtaining selective alpha(1)-adrenoceptors antagonists suitable for development as radioligands for imaging of central alpha(1)-adrenoceptors by positron emission tomography. Sixteen aryl and heteroaryl substituted octoclothepin analogues were prepared by a convergent synthesis via coupling of 1-methyl-4-(8-(4,4.5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10,11-dihydrodibenzo[b,f]thiepin-10yl-piperazine with aryl and heteroaryl halides under palladium catalysis. The most selective compound obtained, (S)-N-(11-(4-methylpiperazin- -yl)-10,11-dihydrodibenzo[b,f]thiepin-2-yl)methyl)isobutyramide (S)-35, showed a similar subnanomolar affinity compared to alpha(1a), alpha(1b,) and alpha(1d)-adrenoceptors and a selectivity ratio of 20, 440, and 20 with respect to D-2, 5-HT2C, and H-1 receptors. respectively.

  DOI：

  10.1021/jm100652h
• 作为产物：
  描述：

  2-(2-(4-bromophenylthio)phenyl)acetic acid 在 polyphosphoric acid 作用下， 反应 1.5h， 以73%的产率得到8-Bromo-10,11-dihydrodibenzothiepin-10-on
  参考文献：
  名称：

  Exploring the Neuroleptic Substituent in Octoclothepin: Potential Ligands for Positron Emission Tomography with Subnanomolar Affinity for α₁-Adrenoceptors

  摘要：

  A series of 1-(10.11-dihydrodthenzo[b,f]thiepin-(10-y-l)-4-methylpiperazine analogues substituted in the 8-position of the 10,11-dihydrodibenzo[b,f]thiepine scaffold with aryl, heteroaryl. amine, and amide substituents are described. The compounds were: designed using the previously reported Liljefors-Bogeso pharmacophore model for dopamine 1)2 and alpha(1)-adrenocetor antagonists. with the aim of obtaining selective alpha(1)-adrenoceptors antagonists suitable for development as radioligands for imaging of central alpha(1)-adrenoceptors by positron emission tomography. Sixteen aryl and heteroaryl substituted octoclothepin analogues were prepared by a convergent synthesis via coupling of 1-methyl-4-(8-(4,4.5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10,11-dihydrodibenzo[b,f]thiepin-10yl-piperazine with aryl and heteroaryl halides under palladium catalysis. The most selective compound obtained, (S)-N-(11-(4-methylpiperazin- -yl)-10,11-dihydrodibenzo[b,f]thiepin-2-yl)methyl)isobutyramide (S)-35, showed a similar subnanomolar affinity compared to alpha(1a), alpha(1b,) and alpha(1d)-adrenoceptors and a selectivity ratio of 20, 440, and 20 with respect to D-2, 5-HT2C, and H-1 receptors. respectively.

  DOI：

  10.1021/jm100652h

文献信息

• 1-thia-3-aza-dibenzoazulenes as inhibitors of tumour necrosis factor production and intermediates for the preparation thereof
  申请人：Mercep Mladen

  公开号：US20060111340A1

  公开（公告）日：2006-05-25

  The present invention relates to derivatives of 1-thia-3-aza-dibenzoazulene class, to their pharmacologically acceptable salts and solvates, to processes and intermediates for the preparation thereof as well as to their antiinflammatory effects, especially to the inhibition of tumour necrosis factor-α (TNF-α) production and the inhibition of interleukin-1 (IL-1) production as well as to their analgetic action.

  本发明涉及1-硫-3-氮杂双苯并吖啶类的衍生物，其药理学上可接受的盐和溶剂，以及其制备过程和中间体，以及它们的抗炎作用，特别是抑制肿瘤坏死因子-α（TNF-α）的产生和抑制白细胞介素-1（IL-1）的产生，以及它们的镇痛作用。
• Azatetracyclische Carbonitrile, ihre Herstellung, pharmazeutische Präparate, die diese enthalten und deren Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0007450A1

  公开（公告）日：1980-02-06

  Azatetracyclische Carbonitrile der Formel 1 in welcher R, Wasserstoff, Niederalkyl, Cycloalkylniederalkyl, Niederalkenyl, freies, veräthertes oder verestertes Hydroxyniederalkyl ist, und X Epoxy, Epithio, Methylen, oder einen zweiwertigen Rest der Teilformel bedeutet, in der Ra Wasserstoff oder Niederalkyl darstellt, und Salze von solchen Verbindungen, ihre Herstellung, pharmazeutische Präparate, die diese enthalten und deren Verwendung.

  式 1 的乙酰四环腈 其中 R 是氢、低级烷基、环烷基-低级烷基、低级烯基、游离的、醚化的或酯化的羟基-低级烷基，X 是环氧基、表硫基、亚甲基或偏式二价基，其中 Ra 是氢或低级烷基。 其中 Ra 是氢或低级烷基，以及这类化合物的盐、其制备方法、含有这类化合物的药物组合物及其用途。
• US4045570A
  申请人：——

  公开号：US4045570A

  公开（公告）日：1977-08-30
• US4263315A
  申请人：——

  公开号：US4263315A

  公开（公告）日：1981-04-21
• US7262302B2
  申请人：——

  公开号：US7262302B2

  公开（公告）日：2007-08-28