5-(3-Methoxypropylaminomethyl)thieno[2,3-b]furan-2-sulfonamide

• 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: 5-(3-Methoxypropylaminomethyl)thieno[2,3-b]furan-2-sulfonamide
• 英文别名: 5-[(3-Methoxypropylamino)methyl]thieno[2,3-b]furan-2-sulfonamide
• 化学式: C₁₁H₁₆N₂O₄S₂
• 分子量: 304.391
• InChiKey: ADYFZNUQNYFYCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-Formylthieno<2,3-b>furan-2-sulfonamide 在 sodium tetrahydroborate 、 3 A molecular sieve 作用下， 以 乙醇 为溶剂， 反应 19.0h， 生成 5-(3-Methoxypropylaminomethyl)thieno[2,3-b]furan-2-sulfonamide
  参考文献：
  名称：

  Thieno[2,3-b]furan-2-sulfonamides as topical carbonic anhydrase inhibitors

  摘要：

  Novel 5-[(alkylamino)methyl]thieno[2,3-b]furan-2-sulfonamides were prepared and evaluated in vitro for inhibition of human carbonic anhydrase II (CA II) and ex vivo for their ability to inhibit CA H in the albino rabbit eye after topical administration. Compound 11a was found to lower intraocular pressure (IOP) in both the alpha-CT ocular hypertensive albino rabbit and the normal albino rabbit, but was ineffective at lowering IOP in a hypertensive, pigmented monkey model Since 11a was highly bound to ocular pigment, a series of less basic analogs was prepared. Examples in this series were both less extensively bound to ocular pigment and more active at reducing IOP in pigmented rabbits after topical dosing. Key examples displayed moderate reactivity toward glutathione.

  DOI：

  10.1021/jm00094a016

文献信息

• Substituted thieno(2,3-B)furan-2-sulfonamides as antiglaucoma agents
  申请人：Merck & Co., Inc.

  公开号：EP0309028A2

  公开（公告）日：1989-03-29

  Thieno[2,3-b]furan-2-sulfonamides are carbonic anhydrase inhibitors useful in the treatment of elevated intraocular pressure and glaucoma.

  噻吩并[2,3-b]呋喃-2-磺酰胺类药物是一种碳酸酐酶抑制剂，可用于治疗眼压升高和青光眼。
• US4798831A
  申请人：——

  公开号：US4798831A

  公开（公告）日：1989-01-17
• Thieno[2,3-b]furan-2-sulfonamides as topical carbonic anhydrase inhibitors
  作者：George D. Hartman、Wasyl Halczenko、John D. Prugh、Robert L. Smith、Michael F. Sugrue、Pierre Mallorga、Stuart R. Michelson、William C. Randall、Harvey Schwam、John M. Sondey

  DOI：10.1021/jm00094a016

  日期：1992.8

  Novel 5-[(alkylamino)methyl]thieno[2,3-b]furan-2-sulfonamides were prepared and evaluated in vitro for inhibition of human carbonic anhydrase II (CA II) and ex vivo for their ability to inhibit CA H in the albino rabbit eye after topical administration. Compound 11a was found to lower intraocular pressure (IOP) in both the alpha-CT ocular hypertensive albino rabbit and the normal albino rabbit, but was ineffective at lowering IOP in a hypertensive, pigmented monkey model Since 11a was highly bound to ocular pigment, a series of less basic analogs was prepared. Examples in this series were both less extensively bound to ocular pigment and more active at reducing IOP in pigmented rabbits after topical dosing. Key examples displayed moderate reactivity toward glutathione.