4-(4-hydroxybenzoyl)thiophene-2-sulfonamide | 118993-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-hydroxybenzoyl)thiophene-2-sulfonamide
• 英文别名: 4-(4-Hydroxybenzoyl)-2-thiophenesulfonamide
• CAS: 118993-57-0
• 化学式: C₁₁H₉NO₄S₂
• 分子量: 283.329
• InChiKey: OJXOXNIZNJIMLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-甲基异丁基胺 、 4-(4-hydroxybenzoyl)thiophene-2-sulfonamide 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 4-<3-<(N-isobutyl-N-methylamino)methyl>-4-hydroxybenzoyl>thiophene-2-sulfonamide
  参考文献：
  名称：

  4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors

  摘要：

  A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potential to act as topically effective ocular hypotensive agents in the ocular normotensive albino rabbit and the ocular alpha-chymotrypsinized rabbit. Solubility studies in water and pH 7.4 buffer were carried out to estimate the ability of compounds to be formulated in solution. The sensitization potential of key representative structures was determined by in vitro glutathione reactivity studies and guinea pig maximization testing.

  DOI：

  10.1021/jm00099a010
• 作为产物：
  描述：

  4-(4-甲氧基苯甲酰基)-2-噻吩磺酰胺 在 氢溴酸 作用下， 反应 8.0h， 以74%的产率得到4-(4-hydroxybenzoyl)thiophene-2-sulfonamide
  参考文献：
  名称：

  新型4-芳基噻吩和呋喃-2-磺酰胺的合成与衍生

  摘要：

  在乙酸酐中区域选择性地用硫酸磺化3-芳基噻吩和呋喃，得到相应的2,4-二取代的杂环。母体磺酰胺的苄胺衍生物可通过芳基酚的曼尼希反应，或通过采用自由基溴化后进行选择性氨解的顺序获得。该方法学提供了对各种区域选择性取代的杂环的容易获得的途径。

  DOI：

  10.1002/jhet.5570260648

文献信息

• Synthesis and derivatization of novel 4-aroylthiophene-and furan-2-sulfonamides
  作者：George D. Hartman、Wasyl Halczenko

  DOI：10.1002/jhet.5570260648

  日期：——

  Sulfonation of 3-aroylthiophenes and furans with sulfuric acid in acetic anhydride regioselectively affords the corresponding 2,4-disubstituted heterocycle. Benzylamine derivatives of the parent sulfonamides are obtained either by Mannich reaction of aryl phenols, or via a sequence employing free radical bromination followed by selective ammonolysis. This methodology provides ready access to a wide

  在乙酸酐中区域选择性地用硫酸磺化3-芳基噻吩和呋喃，得到相应的2,4-二取代的杂环。母体磺酰胺的苄胺衍生物可通过芳基酚的曼尼希反应，或通过采用自由基溴化后进行选择性氨解的顺序获得。该方法学提供了对各种区域选择性取代的杂环的容易获得的途径。
• 4-(benzoyl)thiophene(or furan)-sulfonamide and derivatives thereof for the topical treatment of elevated intraocular pressures
  申请人：Merck & Co., Inc.

  公开号：EP0268396B1

  公开（公告）日：1990-11-28
• HARTMAN, GEORGE D.;HALCZENKO, WASYL, J. HETEROCYCL. CHEM., 26,(1989) N, C. 1793-1798
  作者：HARTMAN, GEORGE D.、HALCZENKO, WASYL

  DOI：——

  日期：——
• Hartman George D., Halczenko Wasyl, Smith Robert L., Sugrue Michael F., M+, J. Med. Chem., 35 (1992) N 21, S 3822-3831
  作者：Hartman George D., Halczenko Wasyl, Smith Robert L., Sugrue Michael F., M+

  DOI：——

  日期：——
• 4-Substituted thiophene- and furan-2-sulfonamides as topical carbonic anhydrase inhibitors
  作者：George D. Hartman、Wasyl Halczenko、Robert L. Smith、Michael F. Sugrue、Pierre J. Mallorga、Stuart R. Michelson、William C. Randall、Harvey Schwam、John M. Sondey

  DOI：10.1021/jm00099a010

  日期：1992.10

  A series of 4-substituted thiophene- and furan-2-sulfonamides was prepared and was found to possess nanomolar-level potency for inhibition of human carbonic anhydrase II in vitro. Selected examples from this group were further evaluated for their potential to act as topically effective ocular hypotensive agents in the ocular normotensive albino rabbit and the ocular alpha-chymotrypsinized rabbit. Solubility studies in water and pH 7.4 buffer were carried out to estimate the ability of compounds to be formulated in solution. The sensitization potential of key representative structures was determined by in vitro glutathione reactivity studies and guinea pig maximization testing.