5-(Dimethylsulfamoylamino)-1,3,4-thiadiazole-2-sulfonamide

• 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-(Dimethylsulfamoylamino)-1,3,4-thiadiazole-2-sulfonamide
• 化学式: C₄H₉N₅O₄S₃
• 分子量: 287.345
• InChiKey: OXCKOUMFAKPIEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-氨基-1,3,4-噻二唑-2-磺酰胺 、 二甲胺基磺酰氯 在 sodium hydroxide 作用下， 生成 5-(Dimethylsulfamoylamino)-1,3,4-thiadiazole-2-sulfonamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors — Part 29 1: Interaction of isozymes I, II and IV with benzolamide-like derivatives

  摘要：

  Reaction of 5-amino-1,3,4-thiadiazole-2-sulfonamide and 5-imino-4-methyl-2-sulfonamido-delta(2)-1,3,4-thiadiazoline with sulfonyl halides/sulfonic acid anhydrides afforded benzolamide-like derivatives possessing very strong inhibitory effects towards three isozymes of carbonic anhydrase (CA), CA I, II and IV. Some of the compounds were designed in such a way to possess good leaving groups (such as nitro-; 2,4,6-triphenyl-pyridinium, etc.) for aromatic nucleophilic substitution reactions with fluoride, in order to introduce positron-emitting isotopes in their molecule, such as F-18. Reactions done initially with the stable isotope of fluorine were not very effective, as the yields in the desired fluoro-derivatives were low, and a complex reaction mixture was obtained. By using this type of approach, and optimizing the synthetic procedure, CA inhibitors for positron emission tomography (PET) applications might be obtained (in the case of utilizing a carrier, which is the non-radioactive derivative itself, since the affinities of such derivatives for the receptor an in the nanomolar range). Further improving of such synthetic procedures might lead to better yields and the respective compounds should be used as selective ligands (also in carrier-free systems) in assessing the role of membrane bound CA isozymes or for new diagnostic tools based on PET. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80042-1