5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide | 32873-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide
• 英文别名: 5-(3-methyl-ureido)-[1,3,4]thiadiazole-2-sulfonic acid amide；3-Methyl-1-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)urea；1-methyl-3-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)urea
• CAS: 32873-77-1
• 化学式: C₄H₇N₅O₃S₂
• 分子量: 237.263
• InChiKey: XCLKHLHNDAHFJT-UHFFFAOYSA-N

物化性质

• 熔点：
  243-245 °C(Solv: ethanol (64-17-5))
• 密度：
  1.741±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  光气 、 5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide 以 乙酸乙酯 为溶剂， 反应 0.5h， 以72%的产率得到2,3-dihydro-3-methyl-2,4-dioxo-4H-<1,3,4>thiadiazolo<3,2-a><1,3,5>triazine-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
• 作为产物：
  描述：

  1-methyl-3-(5-chlorosulfonyl-1,3,4-thiadiazol-2-yl)urea 在 氨 作用下， 以 水 为溶剂， 反应 2.5h， 以98%的产率得到5-(N'-methylureido)-1,3,4-thiadiazole-2-sulfonamide
  参考文献：
  名称：

  Dixon, D. D.; Ford, M. E., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1311 - 1312

  摘要：

  DOI：

文献信息

• DIXON D. D.; FORD M. E., J. HETEROCYCL. CHEM., 1980, 17, NO 6, 1311-1312
  作者：DIXON D. D.、 FORD M. E.

  DOI：——

  日期：——
• 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.
• Dixon, D. D.; Ford, M. E., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1311 - 1312
  作者：Dixon, D. D.、Ford, M. E.

  DOI：——

  日期：——