Thiocarbonic acid O-[6-chloro-2-(3-methoxy-propyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl] ester O-phenyl ester | 880162-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Thiocarbonic acid O-[6-chloro-2-(3-methoxy-propyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl] ester O-phenyl ester
• CAS: 880162-02-7
• 化学式: C₁₇H₁₈ClNO₅S₃
• 分子量: 447.985
• InChiKey: IKWQEVCECWICPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Thiocarbonic acid O-[6-chloro-2-(3-methoxy-propyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl] ester O-phenyl ester 在 正丁基锂 、 Amberlyst-A₂₇ 、 三溴化硼 、 三溴化磷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， -78.0~200.0 ℃ 、66.66 Pa 条件下， 反应 12.83h， 生成 [3-(1,1-Dioxo-6-sulfamoyl-1H-1λ⁶-thieno[3,2-e][1,2]thiazin-2-yl)-propyl]-trimethyl-ammonium; 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：

  6-氯-4-羟基-3,4-二氢-2H-噻吩并[3,2-e][1,2]噻嗪1,1-二氧化物 在 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 Thiocarbonic acid O-[6-chloro-2-(3-methoxy-propyl)-1,1-dioxo-1,2,3,4-tetrahydro-1λ⁶-thieno[3,2-e][1,2]thiazin-4-yl] ester O-phenyl ester
  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