吩噻嗪离子 | 261-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 中文名称: 吩噻嗪离子
• 英文名称: phenothiazinium ion
• 英文别名: 10H-phenothiazine; radical cation；phenothiazinylium；Phenothiazinylkationradikal；Phenothiazinkationradikal；Phenazothionium；phenazthionium；Phenothiazin-5-ium
• CAS: 261-89-2
• 化学式: C₁₂H₈NS
• 分子量: 198.268
• InChiKey: LTOOVISGEYEBFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.73
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吩噻嗪 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 生成 吩噻嗪离子
  参考文献：
  名称：

  Kemp, Terence J.; Moore, Peter; Quick, Geoffrey R., Journal of the Chemical Society. Perkin transactions II, 1980, p. 291 - 295

  摘要：

  DOI：

文献信息

• [EN] METHODS OF CHEMICAL SYNTHESIS OF SUBSTITUTED 10H-PHENOTHIAZINE-3,7-DIAMINE COMPOUNDS<br/>[FR] PROCÉDÉS DE SYNTHÈSE CHIMIQUE DE COMPOSÉS SUBSTITUÉS DE 10H-PHÉNOTHIAZINE-3,7-DIAMINE
  申请人：WISTA LAB LTD

  公开号：WO2017013174A1

  公开（公告）日：2017-01-26

  The present invention pertains generally to the field of chemical synthesis, and more particularly to methods of chemical synthesis which include the step of preparing a substituted 10H-phenothiazine-3,7-diamine compound of Formula (1) by a step of selective alkylation by reductive amination, in which the corresponding unsubstituted diamine of Formula (4) is reacted with aldehyde/ketone, under reductive amination conditions. The present invention also relates to such methods which incorporate additional subsequent and/or preceding steps, for example, to prepare compounds of Formulae (2) and (3) from compounds of Formula (1), and to prepare compounds of Formula (4) from, for example, compounds of Formulae (5), (6), (7), (8), and (9). Compounds of Formula (1), Formula (2), and Formula (3) are useful, for example, in the treatment of diseases of protein aggregation, such as Alzheimer's disease.

  本发明通常涉及化学合成领域，更具体地涉及包括通过还原胺基烷基化步骤来制备配位替代的10H-苯并噻嗪-3,7-二胺化合物的化学合成方法，其中将配位未替代的Formula（4）的二胺与醛/酮在还原胺基化条件下反应。本发明还涉及这种方法，其中包括额外的后续和/或先前步骤，例如，从Formula（1）的化合物制备Formulae（2）和（3）的化合物，以及从Formulae（5）、（6）、（7）、（8）和（9）的化合物制备Formula（4）的化合物。例如，Formula（1）、Formula（2）和Formula（3）的化合物在蛋白质聚集性疾病的治疗中是有用的，例如阿尔茨海默病。
• [EN] METHODS OF CHEMICAL SYNTHESIS OF DIAMINOPHENOTHIAZINIUM COMPOUNDS INCLUDING METHYLTHIONINIUM CHLORIDE (MTC)<br/>[FR] PROCÉDÉS DE SYNTHÈSE CHIMIQUE DE COMPOSÉS DE DIAMINOPHÉNOTHIAZINIUM RENFERMANT DU CHLORURE DE MÉTHYLTHIONINIUM (MTC)
  申请人：WISTA LAB LTD

  公开号：WO2015052496A1

  公开（公告）日：2015-04-16

  Methods of synthesizing and purifying certain 3,7-diamino-phenothiazin-5-ium compounds (referred to herein as "diaminophenothiazinium compounds") including Methythioninium Chloride (MTC) (also known as Methylene Blue) are provided.

  提供了合成和纯化特定的3,7-二氨基苯并噻嗪-5-ium化合物（以下简称为“二氨基苯并噻嗪化合物”）的方法，包括氯甲基噻嗪盐（MTC）（也称为亚甲蓝）。
• [EN] METHODS OF CHEMICAL SYNTHESIS OF DIAMINOPHENOTHIAZINIUM COMPOUNDS INVOLVING THE USE OF PERSULFATE OXIDANTS<br/>[FR] PROCÉDÉS DE SYNTHÈSE CHIMIQUE ET DE COMPOSÉS DE DIAMINOPHÉNOTHIAZINIUM IMPLIQUANT L'UTILISATION D'OXYDANTS DE PERSULFATE
  申请人：WISTA LAB LTD

  公开号：WO2010130977A1

  公开（公告）日：2010-11-18

  This invention pertains generally to the field of chemical synthesis and purification, and more specifically to methods of synthesizing and purifying certain 3,7-diamino- phenothiazin-5-ium compounds (referred to herein as "diaminophenothiazinium compounds") including Methylthioninium Chloride (MTC) (also known as Methylene Blue). In one embodiment, the method comprises the steps of, in order: a thiosulfonic acid formation (TSAF) as illustrated below, wherein the reaction is carried out in the presence of a thiosulfate and an oxidizing agent that is or comprises persulfate an oxidative coupling (OC); and a ring closure (RC). The resulting compounds and compositions comprising them (e.g., tablets, capsules) are useful in methods of medical treatment and diagnosis, etc., for example, tauopathies, or Alzheimer's disease (AD).

  这项发明通常涉及化学合成和纯化领域，更具体地涉及合成和纯化某些3,7-二氨基苯并噻嗪-5-ium化合物（以下简称为"二氨基苯并噻嗪化合物"），包括氯化甲硫蓝（MTC）（又称亚甲蓝）。在一种实施例中，该方法包括按顺序进行以下步骤：如下图所示的硫代磺酸形成（TSAF）步骤，其中在硫代硫酸盐和氧化剂的存在下进行反应，该氧化剂是或包含过硫酸盐；氧化偶联（OC）；和环闭合（RC）。所得的化合物和包含它们的组合物（例如，片剂、胶囊）在医疗治疗和诊断等方法中具有用途，例如对于tau病变或阿尔茨海默病（AD）。
• Antiviral Compounds
  申请人：Hurt Clarence

  公开号：US20120238543A1

  公开（公告）日：2012-09-20

  Novel compounds, methods, and compositions for treating various viral infections are described. In some embodiments the novel compounds of the invention are 3-oxo-phenothiazine derivatives; more specific embodiments include 3-oxo-phenothiazine derivatives having substituents at the 1-, 7-, and 9-positions of the phenothiazine parent ring. In other embodiments, the invention provides compositions and methods for treating viral infections, especially HIV.

  描述了用于治疗各种病毒感染的新型化合物、方法和组合物。在某些实施例中，本发明的新型化合物是3-氧代苯并噻嗪衍生物；更具体的实施例包括在苯并噻嗪母环的1-、7-和9-位置具有取代基的3-氧代苯并噻嗪衍生物。在其他实施例中，本发明提供了用于治疗病毒感染，特别是HIV的组合物和方法。
• 3,7-DIAMINO-10H-PHENOTHIAZINE SALTS AND THEIR USE
  申请人：Wischik Claude Michel

  公开号：US20090054419A1

  公开（公告）日：2009-02-26

  This invention pertains generally to the field of phenothiazine compounds, and more particularly to certain stably reduced phenothiazine compounds, specifically, certain 3,7 diamino-10H-phenothiazine (DAPTZ) compounds of the following formula wherein: each of R 1 and R 9 is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of R 3NA and R 3NB is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of R 7NA and R 7NB is independently selected from: —H; C 1-4 alkyl; C 2-4 alkenyl; and halogenated C 1-4 alkyl; each of HX 1 and HX 2 is independently a protic acid; and pharmaceutically acceptable salts, solvates, and hydrates thereof. These compounds are useful as drugs, for example, in the treatment of tauopathies, such as Alzheimer's disease, and also as prodrugs for the corresponding oxidized thioninium drugs (for example, methythioninium chloride, MTC).

  本发明涉及苯并噻嗪化合物领域，更具体地涉及某些稳定还原的苯并噻嗪化合物，具体而言，涉及以下式子的某些3,7-二氨基-10H-苯并噻嗪(DAPTZ)化合物：其中：R1和R9各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R3NA和R3NB各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；R7NA和R7NB各自独立地选自：—H；C1-4烷基；C2-4烯基；和卤代C1-4烷基；HX1和HX2各自独立地为质子酸；以及其药学上可接受的盐、溶剂化合物和水合物。这些化合物在药物方面具有用途，例如在治疗tau蛋白病中，如阿尔茨海默病，并且作为相应氧化噻唑铵药物（例如甲基噻唑铵盐，MTC）的前药。