3,5-dibromothiophene-2-sulfonamide | 77893-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3,5-dibromothiophene-2-sulfonamide
• CAS: 77893-71-1
• 化学式: C₄H₃Br₂NO₂S₂
• 分子量: 321.013
• InChiKey: OPOWYTIWJCWPSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-dibromo-thiophene-2-sulphonyl chloride 在 ammonium hydroxide 作用下， 以 丙酮 为溶剂， 生成 3,5-dibromothiophene-2-sulfonamide
  参考文献：
  名称：

  Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides

  摘要：

  A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the highest activity, and one analogue, 5-[(4-fluorophenyl)sulfonyl]thiophene-2-sulfonamide (51, UK-17022), had an anticonvulsant ED50 fo 2 mg/kg when administered orally to mice. Compound 51 selectively increased cerebral blood flow in animals without an unacceptable level of diuresis.

  DOI：

  10.1021/jm00140a009

文献信息

• 2,5-dihalothiophenes in the reaction with chlorosulfonic acid
  作者：I. B. Rozentsveig、Yu. A. Aizina、K. A. Chernyshev、L. V. Klyba、E. R. Zhanchipova、E. N. Sukhomazova、L. B. Krivdin、G. G. Levkovskaya

  DOI：10.1134/s1070363207050192

  日期：2007.5

  The mixtures of mono- and dihalothiophenesulfonyl chlorides, formed in the sulfochlorination reaction of 2,5-dichlorothiophene and 2,5-dibromothiophene, were treated with aqueous ammonia and thus converted into mixtures of the corresponding stable thiophenesulfonamides. The structure and composition of C the latter were studied by physicochemical methods: GC-MS and H-1, C-13, H-1-C-13 HSQC, H-1-C-13 HMBC, and NOESY NMR spectroscopy. As a result of the above chemical transformations, 2,5-dichlorothiophene afforded a mixture of 5-chlorothiophene-2-suli'onamide and 4,5-dichlorothiophene-3-sulfonamide in a roughly 70: 30 ratio. In the case of 2,5 -dibromothiophene, a mixture of 5-bromothiophene-2-sulfonamide, 4,5-dibromothiophene-3-sulfonamide, and 3,5-dibromothiophene-2-sulfonamide (3:54:43) was formed.
• Cerebrovasodilatation through selective inhibition of the enzyme carbonic anhydrase. 3. 5-(Arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides
  作者：Ian T. Barnish、Peter E. Cross、Roger P. Dickinson、Michael J. Parry、Michael J. Randall

  DOI：10.1021/jm00140a009

  日期：1981.8

  A series of 5-(arylthio)-, 5-(arylsulfinyl)-, and 5-(arylsulfonyl)thiophene-2-sulfonamides is described and anticonvulsant activities are listed for the compounds. In most cases, the sulfones had the highest activity and the sulfides the least. Sulfones with 3- or 4-halo substituents generally had the highest activity, and one analogue, 5-[(4-fluorophenyl)sulfonyl]thiophene-2-sulfonamide (51, UK-17022), had an anticonvulsant ED50 fo 2 mg/kg when administered orally to mice. Compound 51 selectively increased cerebral blood flow in animals without an unacceptable level of diuresis.