4,5-二溴噻吩-2-磺酰胺 | 77893-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 4,5-二溴噻吩-2-磺酰胺
• 英文名称: 2,3-dibromo-5-thiophenesulfonamide
• 英文别名: 4,5-dibromothiophene-2-sulfonamide
• CAS: 77893-69-7
• 化学式: C₄H₃Br₂NO₂S₂
• mdl: MFCD00208579
• 分子量: 321.013
• InChiKey: XBUBKAHZGMXJBC-UHFFFAOYSA-N

物化性质

• 熔点：
  181-184 °C(Solv: methanol (67-56-1); N,N-dimethylformamide (68-12-2))
• 沸点：
  438.6±55.0 °C(Predicted)
• 密度：
  2.289±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  4,5-二溴噻吩-2-磺酰胺 在 溶剂黄146 、 锌 作用下， 生成 4-bromothiophene-2-sulfonamide
  参考文献：
  名称：

  Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives

  摘要：

  The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.041
• 作为产物：
  描述：

  4,5-二溴噻吩-2-磺酰氯 在 ammonium hydroxide 作用下， 以 丙酮 为溶剂， 生成 4,5-二溴噻吩-2-磺酰胺
  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

• 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.
• Novel inhibitors of prolyl 4-hydroxylase
  作者：Robert I. Dowell、Elizabeth M. Hadley

  DOI：10.1021/jm00083a001

  日期：1992.3

  A series of 5-acyl sulfonamides derived from pyridine-2,5-dicarboxylic acid (15) has been prepared and several members of this series have been shown to be more potent, in vitro, as inhibitors of prolyl 4-hydroxylase than 15. Several chain-extended pyridinedicarboxylic acids have also been prepared and shown to be potent inhibitors of prolyl 4-hydroxylase. The structure-activity in both these series is discussed. The results indicate that the 5-carboxylic acid binding site, in the enzyme, can accept a carboxylic acid or an acyl sulfonamide equally well. This indicates a much greater degree of freedom in this distal carboxylic acid binding site than is predicted by the current theorical model of the active site.
• Sulfonylureas: a new class of cancer chemotherapeutic agents
  作者：Fariborz Mohamadi、Michael M. Spees、Gerald B. Grindey

  DOI：10.1021/jm00094a013

  日期：1992.8

  This study summarizes the antitumor properties of a number of sulofenur thiophene analogs against subcutaneously implanted 6C3HED lymphosarcoma with structural modification of the aryl moiety of the sulfonamide portion of the diarylsulfonylureas. The spectrum of activity of N-(p-chlorophenyl)-N'-[(5-methoxy-2-thienyl)sulfonyl]urea in the HXGC3, VRC5, CX-1, and LX-1 cell lines is also presented.
• BARNISH, I. T.;CROSS, P. E.;DICKINSON, R. P.;PARRY, M. J.;RANDALL, M. J., J. MED. CHEM., 1981, 24, N 8, 959-964
  作者：BARNISH, I. T.、CROSS, P. E.、DICKINSON, R. P.、PARRY, M. J.、RANDALL, M. J.

  DOI：——

  日期：——
• Acyl sulfonamide anti-proliferatives. Part 2: Activity of heterocyclic sulfonamide derivatives
  作者：Mary M. Mader、Chuan Shih、Eileen Considine、Alfonso De Dios、Cora Sue Grossman、Philip A. Hipskind、Ho-Shen Lin、Karen L. Lobb、Beatriz Lopez、José E. Lopez、Luisa M. Martin Cabrejas、Michael E. Richett、Wesley T. White、Yiu-Yin Cheung、Zhongping Huang、John E. Reilly、Sean R. Dinn

  DOI：10.1016/j.bmcl.2004.11.041

  日期：2005.2

  The anti-proliferative activity of acylated heterocyclic sulfonamides is described in Vascular Endothelial Growth Factor-dependent Human Umbilical Vascular Endothelial Cells (VEGF-HUVEC) and in HCT116 tumor cells in a soft agar diffusion assay. (C) 2004 Elsevier Ltd. All rights reserved.