4-bromo-2,5-dichloro-thiophene-3-sulfonamide | 256525-69-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-bromo-2,5-dichloro-thiophene-3-sulfonamide
• 英文别名: 4-bromo-2,5-dichlorothiophene-3-sulfonamide
• CAS: 256525-69-6
• 化学式: C₄H₂BrCl₂NO₂S₂
• 分子量: 311.007
• InChiKey: UAMKYJOZSURAIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 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：

  1-Boc-4-哌啶甲酸 、 4-bromo-2,5-dichloro-thiophene-3-sulfonamide 在 4-二甲氨基吡啶 、 propylphosphonic anhydride 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 4-(4-bromo-2,5-dichloro-thiophene-3-sulfonylaminocarbonyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase

  摘要：

  Steroid sulfatase (STS) is an attractive target for a range of oestrogen- and androgen-dependent diseases. In search of novel chemotypes of STS inhibitors, we had previously identified nortropinyl-arylsulfonylureas 1; however, while these compounds were good inhibitors of purified STS (lowest K-i = 76 nM), they showed only weak inhibition of STS activity in cells (lowest IC50 around 2 muM). Extended structure-activity relationship studies involving modification of the phenylacetyl side chain and replacement of the nortropine element by simpler scaffolds led to the discovery of N-acyl arylsulfonamides, more specifically N-(Boc-piperidine-4-carbonyl)-benzenesulfonamides, as STS inhibitors, some of which exhibit improved cellular potency (best IC50 = 270 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.069
• 作为产物：
  描述：

  4-溴-2,5-二氯噻酚-3-磺酰氯 在 ammonium hydroxide 、 乙酸乙酯 作用下， 反应 16.0h， 生成 4-bromo-2,5-dichloro-thiophene-3-sulfonamide
  参考文献：
  名称：

  N-Acyl arylsulfonamides as novel, reversible inhibitors of human steroid sulfatase

  摘要：

  Steroid sulfatase (STS) is an attractive target for a range of oestrogen- and androgen-dependent diseases. In search of novel chemotypes of STS inhibitors, we had previously identified nortropinyl-arylsulfonylureas 1; however, while these compounds were good inhibitors of purified STS (lowest K-i = 76 nM), they showed only weak inhibition of STS activity in cells (lowest IC50 around 2 muM). Extended structure-activity relationship studies involving modification of the phenylacetyl side chain and replacement of the nortropine element by simpler scaffolds led to the discovery of N-acyl arylsulfonamides, more specifically N-(Boc-piperidine-4-carbonyl)-benzenesulfonamides, as STS inhibitors, some of which exhibit improved cellular potency (best IC50 = 270 nM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.11.069

文献信息

• Acylsulfonamides as inhibitors of steroid sulfatase
  申请人：Horvath Amarylla

  公开号：US20050059712A1

  公开（公告）日：2005-03-17

  A compound of formula wherein R 1 is haloalkyl, alkenyl, phenyl, thienyl, pyridine, benzthiazolyl, chromanyl (1,2-dihydrobenzopyranyl) or (C 6-18 )aryl, and R 1 or R 2 independently of each other are substituted (C 4-8 )cycloalkyl, a substituted bridged cycloalkyl system, substituted piperidine, substituted tetrahydropyridine, or a substituted bridged heterocyclic system, useful as a pharmaceutical.

  化合物的化学式为其中R1为卤代烷基，烯基，苯基，噻吩基，吡啶基，苯并噻唑基，色基（1,2-二氢苯并吡喃基）或（C6-18）芳基，且R1或R2独立地被取代为（C4-8）环烷基，取代的桥式环烷基系统，取代的哌啶，取代的四氢吡啶或取代的桥式杂环系统，可用作药物。
• ANTI-INFLAMMATORY COMPOUNDS
  申请人：Meingassner Josef Gottfried

  公开号：US20090227620A1

  公开（公告）日：2009-09-10

  The use of a steroid sulfatase inhibitor in the preparation of a medicament for the treatment of inflammatory diseases.

  使用类固醇硫酸酯酶抑制剂制备治疗炎症性疾病的药物。
• Combination of a Steroid Sulfatase Inhibitor and an Ascomycin
  申请人：Meingassner Josef Gottfried

  公开号：US20080293758A1

  公开（公告）日：2008-11-27

  A combination of a steroid sulfatase inhibitor and an ascomycin, which combination is useful as a pharmaceutical.

  一种类固醇硫酸酯酶抑制剂和曲霉素的组合物，该组合物可用作药物。
• WO2006/97293
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  公开号：——

  公开（公告）日：——
• WO2006/97292
  申请人：——

  公开号：——

  公开（公告）日：——