3,4-dihydro-2,2-dioxo<1,3,4>thiadiazolo<3,2-c><1,2,4>thiadiazine-7-sulfonamide | 93745-72-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3,4-dihydro-2,2-dioxo<1,3,4>thiadiazolo<3,2-c><1,2,4>thiadiazine-7-sulfonamide
• 英文别名: 2,2-Dioxo-3,4-dihydro-[1,3,4]thiadiazolo[2,3-c][1,2,4]thiadiazine-7-sulfonamide
• CAS: 93745-72-3
• 化学式: C₄H₆N₄O₄S₃
• 分子量: 270.314
• InChiKey: QTABXPUWSGNKCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 乙烯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以60%的产率得到3,4-dihydro-2,2-dioxo<1,3,4>thiadiazolo<3,2-c><1,2,4>thiadiazine-7-sulfonamide
  参考文献：
  名称：

  Synthesis and physicochemical properties of thiadiazolo[3,2-a]pyrimidinesulfonamides and thiadiazolo[3,2-a]triazinesulfonamides as candidates for topically effective carbonic anhydrase inhibitors

  摘要：

  A series of bicyclic 1,3,4-thiadiazolo[3,2-a]pyrimidine- and 1,3,4-thiadiazolo[3,2-a]triazine-7-sulfonamides were synthesized from 5-amino-1,3,4-thiadiazole-2-sulfonamide and evaluated for topical efficacy as ocular hypotensive agents. The compounds were tested for the physicochemical properties of sulfonamide pKa, free acid water solubility, CHCl3/buffer partition, and transcorneal penetration (kin), as well as for activity against carbonic anhydrase (I50). A number of these compounds exhibited lower sulfonamide pKa and higher water solubility than those of acetazolamide (1) and methazolamide (2), and one, 12, brought about a small reduction in IOP in the normal rabbit eye.

  DOI：

  10.1021/jm00394a021

文献信息

• KATRITZKY, ALAN R.;CASTER, KENNETH C.;MAREN, THOMAS H.;CONROY, CURTIS W.;+, J. MED. CHEM., 30,(1987) N 11, 2058-2062
  作者：KATRITZKY, ALAN R.、CASTER, KENNETH C.、MAREN, THOMAS H.、CONROY, CURTIS W.、+

  DOI：——

  日期：——
• Synthesis and physicochemical properties of thiadiazolo[3,2-a]pyrimidinesulfonamides and thiadiazolo[3,2-a]triazinesulfonamides as candidates for topically effective carbonic anhydrase inhibitors
  作者：Alan R. Katritzky、Kenneth C. Caster、Thomas H. Maren、Curtis W. Conroy、Amir Bar-Ilan

  DOI：10.1021/jm00394a021

  日期：1987.11

  A series of bicyclic 1,3,4-thiadiazolo[3,2-a]pyrimidine- and 1,3,4-thiadiazolo[3,2-a]triazine-7-sulfonamides were synthesized from 5-amino-1,3,4-thiadiazole-2-sulfonamide and evaluated for topical efficacy as ocular hypotensive agents. The compounds were tested for the physicochemical properties of sulfonamide pKa, free acid water solubility, CHCl3/buffer partition, and transcorneal penetration (kin), as well as for activity against carbonic anhydrase (I50). A number of these compounds exhibited lower sulfonamide pKa and higher water solubility than those of acetazolamide (1) and methazolamide (2), and one, 12, brought about a small reduction in IOP in the normal rabbit eye.