2-nitro-5-(phenylsulfanyl)phenol | 219765-64-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-nitro-5-(phenylsulfanyl)phenol
• 英文别名: (3-hydroxy-4-nitrophenyl)phenylthioether；2-Nitro-5-phenylsulfanylphenol
• CAS: 219765-64-7
• 化学式: C₁₂H₉NO₃S
• 分子量: 247.274
• InChiKey: FRTOEASNXKEWDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitro-5-(phenylsulfanyl)phenol 在 铁粉 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 47.0h， 生成 tert-butyl 4-(4-phenylsulfonyl-2-hydroxyphenylamino)-3-fluoropiperidin-1-carboxylate
  参考文献：
  名称：

  [EN] FLUOROPIPERIDINE COMPOUNDS AS PURE 5-HT6 RECEPTOR ANTAGONISTS
  [FR] COMPOSÉS DE FLUOROPIPÉRIDINE UTILISÉS EN TANT QU'ANTAGONISTES PURS DU RÉCEPTEUR 5-HT 6

  摘要：

  本发明涉及式(I)的氟哌啶化合物，其立体异构体、同位素形式或药学上可接受的盐作为5-HT6受体拮抗剂。特别是，本发明公开了氟哌啶化合物、其立体异构体、同位素形式或药学上可接受的盐的制备方法、药物组合物、组合及其用途。在式(I)中，R1代表苯基或吡啶基；其中苯基或吡啶基任选地被一个或多个选自卤素、(C1-6)-烷基或卤代(C1-6)-烷基的基团取代；R2代表氢或(C1-6)-烷基；R3代表氢或(C1-6)-烷基；或者R2和R3可以结合在一起形成(C3-6)-环烷基；R4代表氢、(C1-6)-烷基或卤代(C1-6)-烷基；R5代表氢、(C1-6)-烷基、卤代(C1-6)-烷基或-(CH2)0-3-(C3-6)-环烷基。这些化合物可用于治疗由5-羟色胺6受体介导的认知障碍，其中所述认知障碍选自阿尔茨海默病中的痴呆、帕金森病中的痴呆、亨廷顿病中的痴呆、唐氏综合症相关的痴呆、图雷特综合症相关的痴呆、绝经后痴呆、额颞叶痴呆、路易体痴呆、血管性痴呆、HIV中的痴呆、克雅氏病中的痴呆、物质诱发的持续性痴呆、皮克病中的痴呆、精神分裂症中的痴呆、一般医疗条件下的痴呆和老年性痴呆。

  公开号：

  WO2019030641A1
• 作为产物：
  描述：

  3-Methoxy-4-nitro-diphenylsulfid 生成 2-nitro-5-(phenylsulfanyl)phenol
  参考文献：
  名称：

  XASIMOTO, KINDZI;GOTO, KIEXITO;KANOI, KEHNITI;TSUDA, IOSIAKI

  摘要：

  DOI：

文献信息

• Microwave-Promoted TBAF-Catalyzed SNAr Reaction of Aryl Fluorides and ArSTMS: An Efficient Synthesis of Unsymmetrical Diaryl Thioethers
  作者：Xiaochun Yu、Qing Xu、Chuanzhi Liu、Xufeng Zang、Baohua Yu

  DOI：10.1055/s-0030-1259959

  日期：2011.5

  Microwave irradiation was found to promote tetrabutylammonium fluoride catalyzed nucleophilic aromatic substitution of aryl fluorides and arylthiotrimethylsilanes, affording high yields of unsymmetrical diaryl thioethers efficiently under mild, transition-metal- and base-free conditions. Microwave showed unusual improvement on the reaction in not only the conditions and reaction rate, but also in selectivity

  发现微波辐射促进四丁基氟化铵催化芳基氟化物和芳硫基三甲基硅烷的亲核芳香取代，在温和、无过渡金属和无碱的条件下有效地提供高产率的不对称二芳基硫醚。微波不仅在反应条件和反应速率方面，而且在选择性和底物范围方面都表现出异常的改善。
• TBAF-Catalysed Facile Synthesis of Unsymmetrical Diaryl Thioethers via Mild S_NAr Reactions
  作者：Baohua Yu、Xufeng Zang、Xiaochun Yu、Qing Xu

  DOI：10.3184/030823410x12766133486958

  日期：2010.6

  By using tetrabutylammonium fluoride as the catalyst, the synthesis of unsymmetrical diaryl thioethers could be easily achieved in high yields via a mild nucleopilic aromatic substitution reaction of aryl fluorides and phenylthiotrimethylsilane.

  以四丁基氟化铵为催化剂，通过芳基氟化物与苯基硫代三甲基硅烷的温和亲核芳香取代反应，可以轻松地高产率合成不对称的二芳基硫醚。
• Fluoropiperidine compounds as pure 5-HT 6 receptor antagonists
  申请人：SUVEN LIFE SCIENCES LIMITED

  公开号：US10973831B2

  公开（公告）日：2021-04-13

  The present invention relates to fluoropiperidine compounds of formula (I), their stereoisomers, isotopic forms or pharmaceutically acceptable salts thereof as 5-HT6 receptor antagonists. In particular the present invention discloses the methods of preparation, pharmaceutical composition, combinations and use of fluoropiperidine compounds, their stereoisomers, isotopic forms or pharmaceutically acceptable salts thereof.

  本发明涉及作为 5-HT6 受体拮抗剂的式 (I) 氟哌啶化合物、其立体异构体、同位素形式或其药学上可接受的盐。特别是本发明公开了氟哌啶化合物、其立体异构体、同位素形式或其药学上可接受的盐的制备方法、药物组合、组合物和用途。
• NH‐sulfoximine: A novel pharmacological inhibitor of the mitochondrial F ₁ F _o ‐ATPase, which suppresses viability of cancerous cells
  作者：Daniela Strobbe、Rosalba Pecorari、Oriana Conte、Antonella Minutolo、Christine M. M. Hendriks、Stefan Wiezorek、Danilo Faccenda、Rosella Abeti、Carla Montesano、Carsten Bolm、Michelangelo Campanella

  DOI：10.1111/bph.15279

  日期：2021.1

  Background and PurposeThe mitochondrial F1Fo‐ATPsynthase is pivotal for cellular homeostasis. When respiration is perturbed, its mode of action everts becoming an F1Fo‐ATPase and therefore consuming rather producing ATP. Such a reversion is an obvious target for pharmacological intervention to counteract pathologies. Despite this, tools to selectively inhibit the phases of ATP hydrolysis without affecting the production of ATP remain scarce. Here, we report on a newly synthesised chemical, the NH‐sulfoximine (NHS), which achieves such a selectivity.Experimental ApproachThe chemical structure of the F1Fo‐ATPase inhibitor BTB‐06584 was used as a template to synthesise NHS. We assessed its pharmacology in human neuroblastoma SH‐SY5Y cells in which we profiled ATP levels, redox signalling, autophagy pathways and cellular viability. NHS was given alone or in combination with either the glucose analogue 2‐deoxyglucose (2‐DG) or the chemotherapeutic agent etoposide.Key ResultsNHS selectively blocks the consumption of ATP by mitochondria leading a subtle cytotoxicity associated via the concomitant engagement of autophagy which impairs cell viability. NHS achieves such a function independently of the F1Fo‐ATPase inhibitory factor 1 (IF1).Conclusion and ImplicationsThe novel sulfoximine analogue of BTB‐06584, NHS, acts as a selective pharmacological inhibitor of the mitochondrial F1Fo‐ATPase. NHS, by blocking the hydrolysis of ATP perturbs the bioenergetic homoeostasis of cancer cells, leading to a non‐apoptotic type of cell death.
• FLUOROPIPERIDINE COMPOUNDS AS PURE 5-HT6 RECEPTOR ANTAGONISTS
  申请人：Suven Life Sciences Limited

  公开号：EP3649124A1

  公开（公告）日：2020-05-13