(R)-tert-butyl 2-(4-(2-fluoroethoxy)-N-(prop-2-yn-1-yl)phenylsulfonamido)-3-methylbutanoic acid | 1449846-62-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-tert-butyl 2-(4-(2-fluoroethoxy)-N-(prop-2-yn-1-yl)phenylsulfonamido)-3-methylbutanoic acid
• 英文别名: (2R)-2-[[4-(2-fluoroethoxy)phenyl]sulfonyl-prop-2-ynylamino]-3-methylbutanoic acid
• CAS: 1449846-62-1
• 化学式: C₁₆H₂₀FNO₅S
• 分子量: 357.403
• InChiKey: NITRKDKKLTUJLU-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-(4-(2-fluoroethoxy)-N-(prop-2-yn-1-yl)phenylsulfonamido)-3-methylbutanoic acid 在 N-甲基吗啉 、 盐酸 、 copper(ll) sulfate pentahydrate 、 1-羟基苯并三唑 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (R)-2-(4-(2-fluoroethoxy)-N-((1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl)methyl)phenylsulfonamido)-N-hydroxy-3-methylbutanamide
  参考文献：
  名称：

  Inverse 1,2,3-Triazole-1-yl-ethyl Substituted Hydroxamates as Highly Potent Matrix Metalloproteinase Inhibitors: (Radio)synthesis, in Vitro and First in Vivo Evaluation

  摘要：

  Noninvasive imaging and quantification of matrix metalloproteinase (MMP) activity in vivo are of great (pre)clinical interest. This can potentially be realized by using radiolabeled MMP inhibitors (MMPIs) as positron emission tomography (PET) imaging agents. Triazole-substituted MMPIs, discovered by our group, are highly potent inhibitors of MMP-2, -8, -9, and -13. The triazole ring and its position contribute significantly to the potency of the MMP inhibitor. To evaluate structure activity relationships (SARs) of the initially discovered triazole-substituted MMPIs, an additional CH2-group between the backbone of the molecule and the triazole core was inserted, and the triazole ring was "inversed" by switching the alkyne and azide groups. Similar to the original triazole-substituted hydroxamates, the inverse triazole MMPIs are excellent inhibitors with promising in vivo properties. Pharmacokinetic properties and metabolic stability of an F-18-labeled candidate in mice were investigated.

  DOI：

  10.1021/jm4006753
• 作为产物：
  描述：

  (R)-tert-butyl 2-(4-(2-fluoroethoxy)-N-(prop-2-yn-1-yl)phenylsulfonamido)-3-methylbutanoate 在 montmorillonite KSF clay 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以78%的产率得到(R)-tert-butyl 2-(4-(2-fluoroethoxy)-N-(prop-2-yn-1-yl)phenylsulfonamido)-3-methylbutanoic acid
  参考文献：
  名称：

  Inverse 1,2,3-Triazole-1-yl-ethyl Substituted Hydroxamates as Highly Potent Matrix Metalloproteinase Inhibitors: (Radio)synthesis, in Vitro and First in Vivo Evaluation

  摘要：

  Noninvasive imaging and quantification of matrix metalloproteinase (MMP) activity in vivo are of great (pre)clinical interest. This can potentially be realized by using radiolabeled MMP inhibitors (MMPIs) as positron emission tomography (PET) imaging agents. Triazole-substituted MMPIs, discovered by our group, are highly potent inhibitors of MMP-2, -8, -9, and -13. The triazole ring and its position contribute significantly to the potency of the MMP inhibitor. To evaluate structure activity relationships (SARs) of the initially discovered triazole-substituted MMPIs, an additional CH2-group between the backbone of the molecule and the triazole core was inserted, and the triazole ring was "inversed" by switching the alkyne and azide groups. Similar to the original triazole-substituted hydroxamates, the inverse triazole MMPIs are excellent inhibitors with promising in vivo properties. Pharmacokinetic properties and metabolic stability of an F-18-labeled candidate in mice were investigated.

  DOI：

  10.1021/jm4006753