2-amino-6-hydroxy-4,7-dimethylbenzothiazole | 26278-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-amino-6-hydroxy-4,7-dimethylbenzothiazole
• 英文别名: 2-Amino-4,7-dimethyl-6-hydroxybenzothiazole；2-amino-4,7-dimethyl-benzothiazol-6-ol；2-amino-4,7-dimethyl-1,3-benzothiazol-6-ol
• CAS: 26278-83-1
• 化学式: C₉H₁₀N₂OS
• mdl: MFCD04038467
• 分子量: 194.257
• InChiKey: RUTNKAMSWIPHJW-UHFFFAOYSA-N

物化性质

• 沸点：
  399.5±34.0 °C(Predicted)
• 密度：
  1.392±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：7 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  87.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-amino-6-hydroxy-4,7-dimethylbenzothiazole 在 乙酸铵 、 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 6-Hydroxy-4,7-dimethyl-2-(pyridin-3-ylmethyl)aminobenzothiazole
  参考文献：
  名称：

  Novel Dual Inhibitors of 5-Lipoxygenase and Thromboxane A2 Synthetase: Synthesis and Structure-Activity Relationships of 3-Pyridylmethyl-Substituted 2-Amino-6-hydroxybenzothiazole Derivatives

  摘要：

  As part of our search for novel antiinflammatory drug candidates, we have designed and synthesized a series of 3-pyridylmethyl-substituted 2-amino-6-hydroxybenzothiazoles. Introduction of a 3-pyridylmethyl group into the 2-amino group (type-A) or the benzene ring (type-B) of 2-amino-6-hydroxybenzothiazoles imparted dual inhibitory activity against the production by glycogen-induced peritoneal cells of rat (in vitro) of leukotriene B-4 (LTB(4)) and thromboxane A(2) (TXA(2)), while not significantly inhibiting that of prostaglandin E(2) (PGE(2)). The observed inhibition of the former two arachidonic acid metabolites was indicated to be the result of a direct action on 5-Lipoxygenase and TXA(2) synthetase by a cell-free in vitro assay. On the other hand, the inhibitory activities against PGE(2) production were for most compounds very weak, indicating that they did not inhibit cyclooxygenase. Structure-activity relationship studies concerning the position of the 3-pyridylmethyl group revealed that type-B compounds generally showed about 10-fold stronger inhibitory activity against TXA(2) synthetase than type-A compounds. The position of the 3-pyridylmethyl group played an important role in TXA(2) synthetase inhibition. When some of these compounds (8, 13a, 26a (E3040), 26b, 27b, and 28b) were orally administered in the rat TNB/ethanol-induced chronic colitis model (100 mg/ kg), the production of both LTB(4) and TXB(2) in the rat colon was reduced (ex vivo). In addition, one type-B compound, 6-hydroxy-5,7-dimethyl-2-(methylamino)-4 zole (26a), demonstrated a therapeutic effect at treatments of 100 mg/kg po once daily for 11 days and showed almost comparable activity to sulfasalazine at a dose of 500 mg/kg, the reference drug for inflammatory bowel diseases, in this in vivo model.

  DOI：

  10.1021/jm00045a011
• 作为产物：
  描述：

  2,5-二甲基-对苯醌 、 硫脲 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 2-amino-6-hydroxy-4,7-dimethylbenzothiazole
  参考文献：
  名称：

  Reaction of quinones with thiourea. Novel route to 2-amino-6-hydroxybenzothiazoles and 2-amino-5-hydroxynaphtho[1,2-d] thiazoles

  摘要：

  DOI：

  10.1021/jo00837a003
• 作为试剂：
  描述：

  Butyric acid (3aR,4S,7R,7aS)-7-butyryloxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester 在 palladium on activated charcoal sodium hydroxide 、 正丁基锂 、 2-amino-6-hydroxy-4,7-dimethylbenzothiazole 、 硼烷四氢呋喃络合物 、 camphor-10-sulfonic acid 、 氢气 、 双氧水 、 potassium hydride 、 potassium carbonate 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 三苯基膦 、 苯甲酸 、 偶氮二甲酸二乙酯 作用下， 以 水 为溶剂， 反应 87.5h， 生成 5a-carba-α-D-mannopyranose
  参考文献：
  名称：

  Cyclohexane polyols: Enantioselective synthesis of (+)-fortamine and of pseudosugars

  摘要：

  DOI：

  10.1016/s0040-4020(01)85234-0

文献信息

• Inhibitors of polyq-aggregation
  申请人：Bottcher Henning

  公开号：US20050124631A1

  公开（公告）日：2005-06-09

  Compounds of formula I, wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meanings as given in claim 1, and their pharmaceutically tolerable derivatives, solvates and stereoisomers and their use for the preparation of a pharmaceutical for inhibiting the formation of polyQ-aggregation.

  公式I的化合物，其中R1，R2，R3，R4和R5具有声明1中所给定的含义，以及它们的药物可耐受衍生物，溶剂合物和立体异构体，并用于制备用于抑制聚Q聚集物形成的药物。
• INHIBITORS OF POLYQ-AGGREGATION
  申请人：BOTTCHER HENNING

  公开号：US20070259887A1

  公开（公告）日：2007-11-08

  Compounds of formula I, wherein R 1 , R 2 , R 3 , R 4 and R 5 have the meanings as given in claim 1 , and their pharmaceutically tolerable derivatives, solvates and stereoisomers and their use for the preparation of a pharmaceutical for inhibiting the formation of polyQ-aggregation.

  公式I的化合物，其中R1、R2、R3、R4和R5的含义如权利要求1所述，并且它们的药学可耐受衍生物、溶剂合物和立体异构体以及它们的用途用于制备用于抑制聚Q聚集体形成的制药品。
• TREATMENT OF MACROPHAGE-RELATED DISORDERS
  申请人：Neuraltus Pharmaceuticals, Inc.

  公开号：EP2461694A2

  公开（公告）日：2012-06-13
• US9579346B2
  申请人：——

  公开号：US9579346B2

  公开（公告）日：2017-02-28
• [EN] INHIBITORS OF POLYQ-AGGREGATION<br/>[FR] INHIBITEURS DE POLYQ-AGREGATION
  申请人：MAX PLANCK GESELLSCHAFT

  公开号：WO2003015772A1

  公开（公告）日：2003-02-27

  Compounds of formula I, wherein R?1, R2, R3, R4 and R5¿ have the meanings as given in claim 1, and their pharmaceutically tolerable derivatives, solvates and stereoisomers and their use for the preparation of a pharmaceutical for inhibiting the formation of polyQ-aggregation.