4-甲氧基二苯并噻吩 | 24444-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 4-甲氧基二苯并噻吩
• 英文名称: 4-methoxydibenzothiophene
• 英文别名: 4-methoxy-dibenzothiophene；4-Methoxy-dibenzothiophen；4-Methoxydibenzothiophen
• CAS: 24444-74-4
• 化学式: C₁₃H₁₀OS
• 分子量: 214.288
• InChiKey: XISNFPLKXUIFRL-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  371.6±15.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基二苯并噻吩 在 1,1'-双(二苯基膦)二茂铁 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 硝酸 、 potassium acetate 、 吡啶盐酸盐 、 caesium carbonate 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 36.0h， 生成 2-chloro-N-[4-(2-morpholin-4-yl-4-oxo-4H-chromen-8-yl)-dibenzothiophen-1-yl]-acetamide
  参考文献：
  名称：

  1-Substituted (Dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-ones Endowed with Dual DNA-PK/PI3-K Inhibitory Activity

  摘要：

  Analogues of (dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H-chromen-4-one (NU7441), a potent inhibitor of DNA-dependent protein kinase (DNA-PK; IC50 = 42 +/- 2 nM), have been synthesized in which water-solubilizing groups [NHCO(CH2)(n)(NRR2)-R-1, where n = 1 or 2 and the moiety (RRN)-R-1-N-2 was derived from a library of primary and secondary amines, e.g., morpholine] were placed at the 1-position. Several of the newly synthesized compounds exhibited high potency against DNA-PK and potentiated the cytotoxicity of ionizing radiation (IR) in vitro 10-fold or more (e.g., 2-(4-ethyl-piperazin-1-yl)-N-(4-(2-morpholino-4-oxo-4H-chromen-8-yl)-dibenzo[b,d]thio-phen-1-yl)acetamide, 39; DNA-PK IC50 = 5.0 +/- 1 nM, IR dose modification ratio = 13). Furthermore, 39 was shown to potentiate not only IR in vitro but also DNA-inducing cytotoxic anticancer agents, both in vitro and in vivo. Counter-screening against other members of the phosphatidylinositol 3-kinase (PI-3K) related kinase (PIKK) family unexpectedly revealed that some of the compounds were potent mixed DNA-PK and PI-3K inhibitors.

  DOI：

  10.1021/jm400915j
• 作为产物：
  描述：

  二苯并噻吩 在 正丁基锂 、 乙基溴化镁 、 氧气 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 4-甲氧基二苯并噻吩
  参考文献：
  名称：

  [EN] INHIBITORS OF TRKA KINASE
  [FR] INHIBITEURS DE TRKA KINASE

  摘要：

  本发明涉及式I的化合物，该化合物是Tropomyosin-related kinase A（TrkA）的抑制剂：式（I）或其立体异构体、互变异构体或药学上可接受的盐、代谢物、同位素、溶剂合物或前药，其中，Ra、Rb、Rc、Rd、R1、R2、L和Het-Ar如本文所定义。这些化合物可用于预防和/或治疗与神经生长因子（NGF）受体TrkA的异常活动相关的疾病或障碍，如疼痛、炎症或炎症性疾病、癌症、动脉粥样硬化、再狭窄、血栓形成、神经退行性疾病、勃起功能障碍（ED）、皮肤疾病、多发性硬化、干燥综合征、子宫内膜异位症、糖尿病周围神经病变、前列腺炎、传染病、与骨重塑调节失衡相关的疾病、子宫内膜异位症、盆腔疼痛综合征以及由异常组织重塑和纤维化疾病引起的疾病；或与失髓鞘形成或脱髓鞘相关的疾病、障碍、损伤或功能障碍。

  公开号：

  WO2016116900A1

文献信息

• [EN] NOVEL TRICYCLIC COMPOUNDS USEFUL FOR THE TREATMENT OF INFLAMMATORY AND ALLERGIC DISORDERS: PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] NOUVEAUX COMPOSES TRICYCLIQUES UTILES POUR TRAITER LES TROUBLES INFLAMMATOIRES ET ALLERGIQUES, PROCEDE DE PREPARATION DE CES COMPOSES ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：GLENMARK PHARMACEUTICALS LTD

  公开号：WO2004037805A1

  公开（公告）日：2004-05-06

  The present invention relates to novel tricyclic compounds useful for the treatment of inflammatory conditions, diseases of the central nervous and insulin resistant diabetes.

  本发明涉及用于治疗炎症性疾病、中枢神经系统疾病和胰岛素抵抗性糖尿病的新型三环化合物。
• [EN] DNA PK INHIBITORS<br/>[FR] INHIBITEURS DE L'ADN-PK
  申请人：KUDOS PHARM LTD

  公开号：WO2009010761A1

  公开（公告）日：2009-01-22

  A compound of formula (I): wherein: R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, C3-20 heterocydyl group, or C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; X is CH or N; n is 1 or 2; RC1 and RC2 are independently selected from H and methyl; when X is N, Rx is selected from the group consisting of H, and optionally substituted C1-7 alkyl, C3-20 heterocydyl, C5-20 aryl, acyl, ester, amido and sulfonyl; and when X is CH, Rx is selected from the group consisting of H, and optionally substituted C1-7 alkyl, C3-2O heterocyclyl, C5-20 aryl, acyl, ester, amido, sulfonyl, amino and ether. The compounds according to formula (I) are DNA-PK inhibitors, useful in the treatment of tumours and retroviral mediated diseases.

  公式(I)的化合物：其中：R1和R2独立地选自氢、一个可选地取代的C1-7烷基团、C3-20杂环烷基团或C5-20芳基团，或者可以共同形成，连同它们所连接的氮原子，一个从4到8个环原子组成的可选地取代的杂环；X是CH或N；n是1或2；RC1和RC2独立地选自H和甲基；当X是N时，Rx选自由H、和可选地取代的C1-7烷基、C3-20杂环烷基、C5-20芳基、酰基、酯、酰胺和磺酰基组成的组；当X是CH时，Rx选自由H、和可选地取代的C1-7烷基、C3-20杂环烷基、C5-20芳基、酰基、酯、酰胺、磺酰基、氨基和醚组成的组。根据公式(I)的化合物是DNA-PK抑制剂，在治疗肿瘤和逆转录病毒介导的疾病中有效。
• Synthesis of Functionalized Dibenzothiophenes - An Efficient Three-Step Approach Based on Pd-Catalyzed C-C and C-S Bond Formations
  作者：Tue Heesgaard Jepsen、Mogens Larsen、Morten Jørgensen、Katarzyna A. Solanko、Andrew D. Bond、Anders Kadziola、Mogens Brøndsted Nielsen

  DOI：10.1002/ejoc.201001393

  日期：2011.1

  A novel and efficient three-step protocol for synthesizing functionalized dibenzothiophenes (DBTs) from common starting materials and by using palladium-catalyzed carbon-carbon and carbon-sulfur bond formations is presented. The reaction conditions offer significantly improved functional-group tolerance and regioselectivity as compared to previously reported methods.

  提出了一种新颖有效的三步法，用于从常见的起始材料和使用钯催化的碳-碳和碳-硫键形成合成功能化二苯并噻吩 (DBT)。与先前报道的方法相比，反应条件提供了显着改善的官能团耐受性和区域选择性。
• Green Preparation of Dibenzothiophene Derivatives Using 2-Biphenylyl Disulfides in the Presence of Molecular Iodine and Its Application to Dibenzoselenophene Synthesis
  作者：Kota Nishino、Yohei Ogiwara、Norio Sakai

  DOI：10.1002/ejoc.201701155

  日期：2017.10.25

  One-pot preparation of dibenzothiophene derivatives by a green method: Dibenzothiophenes are prepared from 2-biphenylyl disulfides by using molecular iodine as an oxidant. This protocol can lead to the direct preparation of dibenzoselenophene.

  通过绿色方法一锅法制备二苯并噻吩衍生物：用分子碘作为氧化剂由2-联苯基二硫化物制备二苯并噻吩。该方案可导致直接制备二苯并硒基苯。
• [EN] DNA-PK INHIBITORS<br/>[FR] INHIBITEURS D'ADN-PK
  申请人：KUDOS PHARM LTD

  公开号：WO2006032869A1

  公开（公告）日：2006-03-30

  A compound of formula I: and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, wherein: R1 and R2 are independently selected from hydrogen, an optionally substituted C1-7 alkyl group, C3-20 heterocyclyl group, or C5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; Q is -NH-C(=O)- or -O-; Y is an optionally substituted C1-5 alkylene group; X is selected from SR3 or NR4R5, wherein, R3, or R4 and R5 are independently selected from hydrogen, optionally substituted C1-7 alkyl, C5-20 aryl, or C3-20 heterocyclyl groups, or R4 and R5 may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; if Q is -O-, X is additionally selected from -C(=O)-NR6R7, wherein R6 and R7 are independently selected from hydrogen, optionally substituted C1-7 alkyl, C5-20 aryl, or C3-20 heterocyclyl groups, or R6 and R7 may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; and if Q is -NH-C(=O)-, -Y-X may additionally be selected from C1-7 alkyl.

  化合物I的分子式为：及其异构体、盐、溶剂和化学保护形式、以及其前药，其中：R1和R2独立选择氢、可选取代的C1-7烷基、C3-20杂环基或C5-20芳基，或者与它们连接的氮原子一起形成一个可选取代的杂环环，其具有4至8个环原子；Q为-NH-C（=O）-或-O-；Y为可选取代的C1-5烷基；X选自SR3或NR4R5，其中R3，或R4和R5独立选择氢、可选取代的C1-7烷基、C5-20芳基或C3-20杂环基，或者R4和R5可以与它们连接的氮原子一起形成一个可选取代的杂环环，其具有4至8个环原子；如果Q为-O-，X还被选自-C（=O）-NR6R7，其中R6和R7独立选择氢、可选取代的C1-7烷基、C5-20芳基或C3-20杂环基，或者R6和R7可以与它们连接的氮原子一起形成一个可选取代的杂环环，其具有4至8个环原子；如果Q为-NH-C（=O）-，-Y-X还可以被选自C1-7烷基。

表征谱图