4-(ethylamino)-6-(methoxymethyl)-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-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: 4-(ethylamino)-6-(methoxymethyl)-7,7-dioxo-5,6-dihydro-4H-thieno[2,3-b]thiopyran-2-sulfonamide
• 化学式: C₁₁H₁₈N₂O₅S₃
• 分子量: 354.472
• InChiKey: QOFNQPHYXWSVBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  161
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以99%的产率得到
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of NO-Donor Containing Carbonic Anhydrase Inhibitors To Lower Intraocular Pressure

  摘要：

  The antiglaucoma drugs dorzolamide (1) and brinzolamide (2) lower intraocular pressure (TOP) by inhibiting the carbonic anhydrase (CA) enzyme to reduce aqueous humor production. The introduction of a nitric oxide (NO) donor into the alkyl side chain of dorzolamide (1) and brinzolamide (2) has led to the discovery of NO-dorzolamide 3a and NO-brinzolamide 4a, which could lower TOP through two mechanisms: CA inhibition to decrease aqueous humor secretion (reduce inflow) and NO release to increase aqueous humor drainage (increase outflow). Compounds 3a and 4a have shown improved efficacy of lowering IOP in both rabbits and monkeys compared to brinzolamide (2).

  DOI：

  10.1021/acs.jmedchem.5b00043

文献信息

• Design, Synthesis, and Evaluation of NO-Donor Containing Carbonic Anhydrase Inhibitors To Lower Intraocular Pressure
  作者：Qinhua Huang、Eugene Y. Rui、Morena Cobbs、Dac M. Dinh、Hovhannes J. Gukasyan、Jennifer A. Lafontaine、Saurabh Mehta、Brian D. Patterson、David A. Rewolinski、Paul F. Richardson、Martin P. Edwards

  DOI：10.1021/acs.jmedchem.5b00043

  日期：2015.3.26

  The antiglaucoma drugs dorzolamide (1) and brinzolamide (2) lower intraocular pressure (TOP) by inhibiting the carbonic anhydrase (CA) enzyme to reduce aqueous humor production. The introduction of a nitric oxide (NO) donor into the alkyl side chain of dorzolamide (1) and brinzolamide (2) has led to the discovery of NO-dorzolamide 3a and NO-brinzolamide 4a, which could lower TOP through two mechanisms: CA inhibition to decrease aqueous humor secretion (reduce inflow) and NO release to increase aqueous humor drainage (increase outflow). Compounds 3a and 4a have shown improved efficacy of lowering IOP in both rabbits and monkeys compared to brinzolamide (2).