2-(2-Hydroxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1, 2-thiazine-6-sulfonamide 1,1-dioxide | 171273-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻嗪类
• 英文名称: 2-(2-Hydroxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1, 2-thiazine-6-sulfonamide 1,1-dioxide
• 英文别名: 2-(2-Hydroxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide；2-(2-hydroxyethyl)-3-(morpholin-4-ylmethyl)-1,1-dioxothieno[3,2-e]thiazine-6-sulfonamide
• CAS: 171273-06-6
• 化学式: C₁₃H₁₉N₃O₆S₃
• 分子量: 409.508
• InChiKey: JHTLZMXVNYOKAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(2-Hydroxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1, 2-thiazine-6-sulfonamide 1,1-dioxide 在 氯化亚砜 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2',2'-Dioxospiro[1,4-oxazinan-4-ium-4,11'-2lambda6,4-dithia-1-aza-11-azoniatricyclo[7.4.0.03,7]trideca-3(7),5,8-triene]-5'-sulfonamide;chloride
  参考文献：
  名称：

  Quaternary ammonium substituted thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase

  摘要：

  Thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quatemary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as 15 and 16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as 14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.054
• 作为产物：
  描述：

  2-(2-Methoxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxide 在 氢溴酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 以56%的产率得到2-(2-Hydroxyethyl)-3-(4-morpholinylmethyl)-2H-thieno[3,2-e]-1, 2-thiazine-6-sulfonamide 1,1-dioxide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors

  摘要：

  披露了具有以下公式的化合物：本发明涉及公式I的化合物：##STR1## 其中G，J以及它们所连接的噻吩环上的两个原子形成一个六元环，选自##STR2## 这些化合物作为碳酸酐酶抑制剂是有用的。

  公开号：

  US05538966A1

文献信息

• US5538966A
  申请人：——

  公开号：US5538966A

  公开（公告）日：1996-07-23
• Quaternary ammonium substituted thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides: Potential membrane-impermeable inhibitors of carbonic anhydrase
  作者：Jesse A. May、Abdelmoula Namil、Hwang-Hsing Chen、Anura P. Dantanarayana、Brian Dupré、John C. Liao

  DOI：10.1016/j.bmc.2005.10.054

  日期：2006.3

  Thieno[3,2-e]-1,2-thiazine-6-sulfonamide 1,1-dioxides, which have a quaternary ammonium moiety incorporated into their structures, were synthesized. All of the quaternary ammonium salts prepared in the present study are potent inhibitors of both human carbonic anhydrase-II and recombinant human carbonic anhydrase-IV; they are significantly more potent as inhibitors of these carbonic anhydrase isozymes than the previously reported inhibitor quatemary ammonium homosulfanilamide. By virtue of the permanent cationic charge on these compounds they are anticipated to be membrane-impermeable inhibitors of carbonic anhydrase. Spiro quaternary ammonium compounds, such as 15 and 16, when formed by intracellular cyclization following transport of a suitable precursor molecule, such as 14, may be selective prolonged inhibitors of cytosolic carbonic anhydrase due to intracellular entrapment. (c) 2005 Elsevier Ltd. All rights reserved.
• Carbonic anhydrase inhibitors
  申请人：Alcon Laboratories, Inc.

  公开号：US05538966A1

  公开（公告）日：1996-07-23

  Compounds of the following formula are disclosed: Compounds of Formula I are the topic of this invention: ##STR1## Wherein G, J and the two atoms of the thiophene ring to which they are attached form a six-membered ring chosen from ##STR2## The compounds are useful as carbonic anhydrase inhibitors.

  披露了具有以下公式的化合物：本发明涉及公式I的化合物：##STR1## 其中G，J以及它们所连接的噻吩环上的两个原子形成一个六元环，选自##STR2## 这些化合物作为碳酸酐酶抑制剂是有用的。