2-hydroxyphenothiazine | 24316-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-hydroxyphenothiazine
• 英文别名: 10H-phenothiazin-2-ol；phenothiazin-2-ol；2-hydroxy-10H-phenothiazine；10H-phenothiazin-2-ol
• CAS: 24316-35-6
• 化学式: C₁₂H₉NOS
• 分子量: 215.276
• InChiKey: OJQOKLSLPLGDBX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 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：
  57.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxyphenothiazine 在 sodium hydroxide 作用下， 以 二甲基亚砜 、 异丙醇 为溶剂， 生成 1-{[2-(2-methoxyphenoxy)ethyl]amino}-1-(10H-phenothiazin-2-yloxy)-2-propanol
  参考文献：
  名称：

  Novel Carvedilol Analogues That Suppress Store-Overload-Induced Ca²⁺ Release

  摘要：

  Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the beta-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

  DOI：

  10.1021/jm401090a
• 作为产物：
  描述：

  2-甲氧基酚噻嗪 在 吡啶盐酸盐 作用下， 反应 12.0h， 以69%的产率得到2-hydroxyphenothiazine
  参考文献：
  名称：

  吩噻嗪类作为脂质过氧化抑制剂和细胞保护剂。

  摘要：

  合成了一系列吩噻嗪，并将其作为铁依赖性脂质过氧化的体外抑制剂进行评估。2-（10H-吩噻嗪-2-基氧基）-N，N-二甲基乙醇胺甲磺酸盐（6）的MIC（给出大于或等于50％抑制作用的最低测试浓度）为0.26 microM。尽管在N-10处的甲基取代使活性降低了近100倍，但其他结构修饰（例如改变胺基，将胺取代基与吩噻嗪核之间的距离以及连接基团）影响很小。通过竞争性清道夫受体介导的小鼠腹膜巨噬细胞体外降解125I标记的乙酰基LDL，化合物6在抑制低密度脂蛋白（LDL）的Cu2 +催化的氧化中比普罗布考更有效。

  DOI：

  10.1021/jm00082a012

文献信息

• Antioxidant Activities of Phenothiazines and Related Compounds: Correlation between the Antioxidant Activities and Dissociation Energies of O–H or N–H Bonds
  作者：Tatsuo Yamamura、Kyouichi Suzuki、Tatsuya Yamaguchi、Tomihiro Nishiyama

  DOI：10.1246/bcsj.70.413

  日期：1997.2

  The antioxidant activities of phenothiazines, carbazoles, and related diphenylamines were evaluated in the oxidation of tetralin at 60 °C and linoleic acid micelles in aqueous dispersion at 37 °C induced by an azo initiator. Phenothiazines were highly antioxidant in both systems. Although diphenylamine and carbazole were not good antioxidants, those having a hydroxy group as a substituent at the ortho

  吩噻嗪、咔唑和相关二苯胺的抗氧化活性在由偶氮引发剂诱导的 60°C 萘满和 37°C 水分散体中的亚油酸胶束氧化中进行评估。吩噻嗪在两个系统中都具有很强的抗氧化性。尽管二苯胺和咔唑不是很好的抗氧化剂，但那些在氨基的邻位或对位具有羟基取代基的化合物是有效的抗氧化剂。由于苯氧基自由基的稳定性，邻羟基二苯胺的抗氧化活性比两个系统中的其他化合物都要大得多，这是因为未配对电子离域到氨基的 p 型孤对电子。应用半经验MNDO-AM1计算来研究自氧化链式过程中抗氧化剂的夺氢。
• Phenothiazine Derivatives. IV. Reactions of Thionyl Chloride with Some Substituted Diphenylamines and with NaphthylphenyIamines
  作者：Manabu Fujimoto

  DOI：10.1246/bcsj.32.296

  日期：1959.3

  Reactions of thionyl chloride with some substituted diphenylamines and with naphthylphenylamines were studied. N-Acetyldiphenylamine gave the known 1,3,7,9-tetrachlorophenothiazine. Methyldiphenylamine gave a small yield of the known 3,7-dichloro-10-methylphenothiazine besides the same tetrachlorophenothiazine as the main product. The following new compounds were obtained from respective starting materials

  研究了亚硫酰氯与一些取代的二苯胺和萘基苯胺的反应。N-乙酰二苯胺得到已知的 1,3,7,9-四氯吩噻嗪。除了与主要产物相同的四氯吩噻嗪之外，甲基二苯胺产生少量已知的 3,7-二氯-10-甲基吩噻嗪。从各自的起始材料中获得了以下新化合物并推导了它们的结构：来自三苯胺的 3,7-二氯-10-(4'-氯苯基)-吩噻嗪，来自 3 的 1,3,7,9-四氯-2-羟基吩噻嗪-羟基二苯胺，2,4,7,9-四氯-3-吩噻酮来自4-羟基二苯胺，3-氨基-2,4,7,9-四氯吩噻吩氯化物来自4-氨基二苯胺，3,7-二氨基-2,4，来自 4,4'-二氨基二苯胺、3-氨基 2,4,6 的 6,8-四氯吩硫鎓氯化物，
• N-(iminomethyl)amines derivatives, their preparation, their use as medicines and compositions containing them
  申请人：Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.)

  公开号：US06482822B1

  公开（公告）日：2002-11-19

  The invention concerns novel N-(iminomethyl)amine derivatives comprising in their skeleton the aminophenylamine, oxodiphenylamine, carbazole, phenazine, phenoxazine or oxodiphenyl motif, their use as medicines and pharmaceutical compositions containing them. The invention concerns in particular the following compounds: -4-{[2-thienyl(imino)methyl]amino}-N-[2-(phenylamino)phenyl]-benzenebutanamide; -4-{[2-thienyl(imino)methyl]amino}-N-[4-(phenylamino)phenyl]-benzenebutanamide; -N-′[4-(10H-phenothiazin-2-yloxy)phenyl]-2-thiophenecarboximidamide; -4-(4-{[amino(2-thienyl)methylidene]amino}phenyl)-N-(10H-phenothiazin-3-ylH)butanamide; -3-[(3-{[amino(2-thienyl)methylidene]amino}-benzyl)amino]-N-(4-anilinophenyl)propanamide; -N′-(4-{2-[(10H-phenothiazin-3-ylmethyl)amino]ethyl}phenyl-2-thiophene carboximidamide.

  该发明涉及新颖的N-(亚甲基亚胺)胺衍生物，其骨架中包含氨基苯胺、氧代二苯胺、咔唑、苯并嗪、苯氧嗪或氧代二苯基团，以及它们作为药物的用途和含有它们的药物组合物。该发明特别涉及以下化合物：-4-【2-噻吩基(亚甲基)氨基】-N-[2-(苯胺基)苯基]苯丁酰胺；-4-【2-噻吩基(亚甲基)氨基】-N-[4-(苯胺基)苯基]苯丁酰胺；-N-′[4-(10H-苯并噻嗪-2-氧基)苯基]-2-噻吩羧酰亚胺；-4-(4-【氨基(2-噻吩基)甲基亚胺】苯基)-N-(10H-苯并噻嗪-3-基)丁酰胺；-3-[(3-【氨基(2-噻吩基)甲基亚胺】苯基)-N-(4-苯胺基苯基)丙酰胺；-N′-(4-[2-(10H-苯并噻嗪-3-基甲基)氨基]乙基苯基-2-噻吩羧酰亚胺。
• PROCESS FOR THE PREPARATION OF IMIDES AND DERIVATIVES THEREOF AND USES
  申请人：Jacquot Roland

  公开号：US20130327988A1

  公开（公告）日：2013-12-12

  A process for the preparation of imides and also the uses thereof, especially as intermediates for the preparation of solvents, in particular of diester solvents, is described. Further described is a process for preparing cyclic imides and derivatives thereof, especially the corresponding carboxylic acids.

  一种制备亚酰胺及其用途的方法，特别是作为溶剂制备的中间体，特别是二酯溶剂的制备中间体的方法被描述。进一步描述了一种制备环状亚酰胺及其衍生物的方法，特别是相应的羧酸。
• Microwave-Assisted Phenothiazines Preparation by Thionation of Diphenylamines
  作者：Sorin V. FILIP、Ioan A. SILBERG、Emanoil SURDUCAN、Mircea VLASSA、Vasile SURDUCAN

  DOI：10.1080/00397919808005727

  日期：1998.1

  Abstract A preparation in ‘dry media’ of phenothiazine derivatives by thionation of diphenylamines using microwave-activation is presented. This method allowed the preparation of 2,4,6,8-tetra-tert-butyl-10H-phenothiazine 2e, the first 2,4,6,8-tetra-substituted derivative of this heterocycle, practically inaccessible by other thionation procedure.

  摘要 介绍了一种在“干燥介质”中通过使用微波活化二苯胺硫化作用制备吩噻嗪衍生物的方法。该方法允许制备 2,4,6,8-四-叔丁基-10H-吩噻嗪 2e，这是该杂环的第一个 2,4,6,8-四取代衍生物，其他硫化过程几乎无法获得。