2-amino-5-dimethylaminophenyl thiosulfonic acid | 65517-31-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-amino-5-dimethylaminophenyl thiosulfonic acid
• 英文别名: 2-Amino-5-dimethylaminophenylthiosulfonic acid；2-hydroxysulfonothioyl-4-N,4-N-dimethylbenzene-1,4-diamine
• CAS: 65517-31-9
• 化学式: C₈H₁₂N₂O₂S₂
• 分子量: 232.327
• InChiKey: WHLSUYBVBOSJOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-5-dimethylaminophenyl thiosulfonic acid 在 盐酸 、 potassium dichromate 、 manganese(IV) oxide 、 copper(II) sulfate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 73.5h， 生成 3-Dimethylamino-7-{[4-(2,5-dioxo-pyrrolidin-1-yloxycarbonyl)-butyl]-methyl-amino}-phenothiazin-5-ylium; chloride
  参考文献：
  名称：

  Covalent Attachment of Methylene Blue to Oligonucleotides

  摘要：

  The synthesis and application of oligonucleotides derivatized by methylene blue are described. For that, a carboxylated methylene blue derivative was synthesized and transformed into an activated N-hydroxysuccinimidoester. The activated ester was reacted with 5'-aminoalkylated oligonucleotides. The labelled oligonucleotides were isolated and characterized both by reversed phase HPLC and MALDI mass spectrometry. Initial studies on analytical application of these oligonucleotide conjugates are discussed.

  DOI：

  10.1080/15257779508010703
• 作为产物：
  描述：

  N,N-二甲基对苯二胺硫酸盐 在 potassium dichromate 、 aluminum(III) sulfate 、 sodium thiosulfate 、 zinc(II) chloride 作用下， 以 正庚烷 为溶剂， 反应 2.5h， 以49%的产率得到2-amino-5-dimethylaminophenyl thiosulfonic acid
  参考文献：
  名称：

  [EN] FUSED PHENOTHIAZINIUM COMPOUNDS, PREPARATION METHOD THEREOF AND USE AS PHOTOANTIMICROBIALS
  [FR] COMPOSÉS, PROCÉDÉ ET UTILISATION

  摘要：

  公开号：

  WO2009047534A3

文献信息

• [EN] TOLUIDINE BLUE DERIVATIVES AS PHOTOSENSITISING COMPOUNDS<br/>[FR] DÉRIVÉS DE BLEU DE TOLUIDINE UTILISÉS EN TANT QUE COMPOSÉS DE PHOTOSENSIBILISATION
  申请人：PHARMALUCIA LTD

  公开号：WO2011114137A1

  公开（公告）日：2011-09-22

  A compound of formula (III), or a pharmaceutically acceptable derivative thereof for use in a method of combating and/or detecting a pathogen and/or tumour cells; wherein X is selected from O, S and Se; each of R2, R3 and R4 is independently selected from hydrogen or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; and R1 is selected from halogen, sulfo, acyl, sulfoxy, mercapto, nitro, amino, hydroxy or an optionally substituted alkyl, alkenyl, alkynyl, aryl, amine or alkoxy group; wherein R1 is not methyl or hydrogen when each of R3 and R4 is methyl or hydrogen.

  一种化合物的化学式（III），或其药学上可接受的衍生物，用于抗击和/或检测病原体和/或肿瘤细胞的方法；其中X从O、S和Se中选择；R2、R3和R4中的每一个独立地从氢或可选择取代的烷基、烯基、炔基或芳基中选择；R1从卤素、磺酰、酰基、磺氧基、巯基、硝基、氨基、羟基或可选择取代的烷基、烯基、炔基、芳基、胺基或烷氧基中选择；其中当R3和R4中的每一个是甲基或氢时，R1不是甲基或氢。
• TOLUIDINE BLUE DERIVATIVES AS PHOTOSENSITISING COMPOUNDS
  申请人：Wainwright Mark

  公开号：US20120328530A1

  公开（公告）日：2012-12-27

  A compound of formula (III), or a pharmaceutically acceptable derivative thereof for use in a method of combating and/or detecting a pathogen and/or tumour cells; wherein X is selected from O, S and Se; each of R 2 , R 3 and R 4 is independently selected from hydrogen or an optionally substituted alkyl, alkenyl, alkynyl or aryl group; and R 1 is selected from halogen, sulfo, acyl, sulfoxy, mercapto, nitro, amino, hydroxy or an optionally substituted alkyl, alkenyl, alkynyl, aryl, amine or alkoxy group; wherein R 1 is not methyl or hydrogen when each of R 3 and R 4 is methyl or hydrogen.

  公式（III）的化合物，或其药学上可接受的衍生物，用于对抗和/或检测病原体和/或肿瘤细胞的方法；其中X从O、S和Se中选择；R2、R3和R4中的每一个独立地选择自氢或一个可选择地取代的烷基、烯基、炔基或芳基；R1从卤素、磺酰、酰基、磺氧基、巯基、硝基、氨基、羟基或一个可选择地取代的烷基、烯基、炔基、芳基、胺基或烷氧基中选择；其中当R3和R4中的每一个是甲基或氢时，R1不是甲基或氢。
• [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）。
• [EN] NOVEL IMPROVED METHOD FOR SYNTHESIZING DIAMINOPHENOTHIAZINE COMPOUNDS<br/>[FR] NOUVEAU PROCÉDÉ AMÉLIORÉ POUR SYNTHÈSE DE COMPOSÉS DE DIAMINOPHÉNOTHIAZINE
  申请人：AGRAWAL ACHAL NARENDRAKUMAR

  公开号：WO2020250186A1

  公开（公告）日：2020-12-17

  The present invention relates to chemical synthesis and purification. Specifically, the present invention relates to a novel and improved method of synthesizing high purity diaminophenothiazine compounds of Formula I, specifically Methylene Blue and its pharmaceutically acceptable salt or hydrates thereof. The present invention relates to an improved method of synthesizing Methylene Blue compound of higher purities than those achievable by using known methods of synthesis as per the requirements of the international pharmacopoeias like USP and EP.

  本发明涉及化学合成和纯化。具体来说，本发明涉及一种新颖且改进的方法，用于合成高纯度的二氨基苯噻嗪化合物（化学式I），特别是亚甲蓝及其药用可接受盐或水合物。本发明涉及一种改进的方法，用于合成比使用已知合成方法更高纯度的亚甲蓝化合物，以满足国际药典如美国药典和欧洲药典的要求。
• METHODS OF CHEMICAL SYNTHESIS OF DIAMINOPHENOTHIAZINIUM COMPOUNDS INVOLVING THE USE OF PERSULFATE OXIDANTS
  申请人：Larch Christopher Paul

  公开号：US20120058995A1

  公开（公告）日：2012-03-08

  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 e//i 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 thio sulfate 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).

  本发明涉及化学合成和纯化领域，更具体地涉及合成和纯化某些3,7-二氨基苯并噻吩-5-ium化合物（以下简称“二氨基苯并噻吩化合物”），包括氯化甲基硫菲尼（MTC）（也称为亚甲蓝）。在一种实施例中，e//i方法包括以下步骤：首先进行硫代磺酸形成（TSAF），反应在硫代硫酸盐和氧化剂（或包含过硫酸盐）的存在下进行；然后进行氧化偶联（OC）；最后进行环闭合（RC）。所得化合物及其组合物（例如，片剂、胶囊）在医疗治疗和诊断等方面有用，例如用于治疗tau蛋白病或阿尔茨海默病（AD）。