(R)-2-(3-bromopropyl)-4-(ethylamino)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide | 187722-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻嗪类
• 英文名称: (R)-2-(3-bromopropyl)-4-(ethylamino)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide
• 英文别名: (4R)-2-(3-bromopropyl)-4-(ethylamino)-3,4-dihydro-2H-thieno[3,2-e][1,2]thiazine-6-sulfonamide-1,1-dioxide；(4R)-2-(3-bromopropyl)-4-(ethylamino)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide
• CAS: 187722-04-9
• 化学式: C₁₁H₁₈BrN₃O₄S₃
• 分子量: 432.384
• InChiKey: SXKKWDJTPYUNCE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  155
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-(3-bromopropyl)-4-(ethylamino)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide 在 硝酸 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以28%的产率得到(R)-3-(4-(ethylamino)-1,1-dioxido-6-sulfamoyl-3,4-dihydro-2Hthieno[3,2-e][1,2]thiazin-2-yl)propyl nitrate
  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
• 作为产物：
  描述：

  布林佐胺杂质C 在 氢溴酸 作用下， 以 水 为溶剂， 反应 18.0h， 以54%的产率得到(R)-2-(3-bromopropyl)-4-(ethylamino)-3,4-dihydro-2H-thieno-[3,2-e][1,2]thiazine-6-sulfonamide 1,1-dioxide
  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

• WO2008/120099
  申请人：——

  公开号：——

  公开（公告）日：——