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。
• Reaction of quinones with thiourea. Novel route to 2-amino-6-hydroxybenzothiazoles and 2-amino-5-hydroxynaphtho[1,2-d] thiazoles
  作者：Philip T. S. Lau、T. E. Compf

  DOI：10.1021/jo00837a003

  日期：1970.12
• 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