[(3R,5S)-5-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamoyl]-1-[(2S)-2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)carbamoylamino]-3,3-dimethyl-butanoyl]pyrrolidin-3-yl] 4-fluoroisoindoline-2-carboxylate | 1285533-22-3

• 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: [(3R,5S)-5-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamoyl]-1-[(2S)-2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)carbamoylamino]-3,3-dimethyl-butanoyl]pyrrolidin-3-yl] 4-fluoroisoindoline-2-carboxylate
• 英文别名: [(3R,5S)-5-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-1-[(2S)-2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)carbamoylamino]-3,3-dimethylbutanoyl]pyrrolidin-3-yl] 4-fluoro-1,3-dihydroisoindole-2-carboxylate
• CAS: 1285533-22-3
• 化学式: C₃₇H₄₃BF₂N₆O₁₀S
• 分子量: 812.656
• InChiKey: IPEGMHPWNUADCU-OOHWABCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  57
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  221
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  (3R,5S)-1-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-5-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)pyrrolidin-3-yl 4-fluoroisoindoline-2-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 [(3R,5S)-5-[[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-vinyl-cyclopropyl]carbamoyl]-1-[(2S)-2-[(5-fluoro-1-hydroxy-3H-2,1-benzoxaborol-6-yl)carbamoylamino]-3,3-dimethyl-butanoyl]pyrrolidin-3-yl] 4-fluoroisoindoline-2-carboxylate
  参考文献：
  名称：

  Synthesis and SAR of acyclic HCV NS3 protease inhibitors with novel P4-benzoxaborole moieties

  摘要：

  We have synthesized and evaluated a new series of acyclic P4-benzoxaborole-based HCV NS3 protease inhibitors. Structure-activity relationships were investigated, leading to the identification of compounds 5g and 17 with low nanomolar potency in the enzymatic and cell-based replicon assay. The linker-truncated compound 5j was found to exhibit improved absorption and oral bioavailability in rats, suggesting that further reduction of molecular weight and polar surface area could result in improved drug-like properties of this novel series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.006