6-甲氧基-4,5,7-三甲基-2-<(3-吡啶基甲基)氨基>苯并噻唑 | 145096-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 6-甲氧基-4,5,7-三甲基-2-<(3-吡啶基甲基)氨基>苯并噻唑
• 英文名称: 6-methoxy-4,5,7-trimethyl-2-<(3-pyridylmethyl)amino>benzothiazole
• 英文别名: 6-Methoxy-4,5,7-trimethyl-2-(pyridin-3-ylmethyl)aminobenzothiazole；6-Methoxy-4,5,7-trimethyl-2-(3-pyridylmethyl)aminobenzothiazole；2-Benzothiazolamine, 6-methoxy-4,5,7-trimethyl-N-(3-pyridinylmethyl)-；6-methoxy-4,5,7-trimethyl-N-(pyridin-3-ylmethyl)-1,3-benzothiazol-2-amine
• CAS: 145096-22-6
• 化学式: C₁₇H₁₉N₃OS
• 分子量: 313.423
• InChiKey: NXVVAGCCKWWDAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-甲氧基-4,5,7-三甲基-2-<(3-吡啶基甲基)氨基>苯并噻唑 在 三溴化硼 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 生成 6-Hydroxy-4,5,7-trimethyl-2-(pyridin-3-ylmethyl)aminobenzothiazole
  参考文献：
  名称：

  Pyridyl substituted benzothiazole compounds which have useful

  摘要：

  一种苯并噻唑衍生物或其药学上可接受的盐，可用作预防或治疗抑制白三烯和血栓素产生功能有效的疾病的药物。一种由以下通式（I）表示的苯并噻唑衍生物：##STR1## 其中R.sup.1和R.sup.3相同或不同，表示氢原子，低级烷基或低级烷氧基; R.sup.4表示由式--(CH.sub.x)--.sub.q表示的基团，其中q为1至4的整数; R.sup.2表示氢原子; R.sup.5和R.sup.6相同或不同，每个表示氢原子或低级烷基; 或其药学上可接受的盐。

  公开号：

  US05300518A1
• 作为产物：
  描述：

  氯化烟碱盐酸盐 在 吡啶 、 盐酸 、 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成 6-甲氧基-4,5,7-三甲基-2-<(3-吡啶基甲基)氨基>苯并噻唑
  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

文献信息

• Pyridyl substituted benzothiazole compounds which have useful
  申请人：Eisai Co., Ltd.

  公开号：US05300518A1

  公开（公告）日：1994-04-05

  A benzothiazole derivative or a pharmacologically acceptable salt thereof which is useful as a preventive or therapeutic agent for diseases on which functions of suppressing leukotrienes and thromboxanes production are effective. A benzothiazole derivative represented by the following general formula (I): ##STR1## wherein R.sup.1 and R.sup.3 are either the same or different and represents a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.4 represents a group represented by the formula --(CH.sub.x)--.sub.q wherein q is a integer of from 1 to 4; R.sup.2 represents a hydrogen atom and; R.sup.5 and R.sup.6 are the same or different and each represent a hydrogen atom or a lower alkyl group; or a pharmacologically acceptable salt thereof.

  一种苯并噻唑衍生物或其药学上可接受的盐，可用作预防或治疗抑制白三烯和血栓素产生功能有效的疾病的药物。一种由以下通式（I）表示的苯并噻唑衍生物：##STR1## 其中R.sup.1和R.sup.3相同或不同，表示氢原子，低级烷基或低级烷氧基; R.sup.4表示由式--(CH.sub.x)--.sub.q表示的基团，其中q为1至4的整数; R.sup.2表示氢原子; R.sup.5和R.sup.6相同或不同，每个表示氢原子或低级烷基; 或其药学上可接受的盐。
• Benzothiazole derivative
  申请人：Eisai Co., Ltd.

  公开号：EP0507318B1

  公开（公告）日：1997-09-10
• US5300518A
  申请人：——

  公开号：US5300518A

  公开（公告）日：1994-04-05
• US5420144A
  申请人：——

  公开号：US5420144A

  公开（公告）日：1995-05-30
• US5635519A
  申请人：——

  公开号：US5635519A

  公开（公告）日：1997-06-03