(4S)-1-BOC-4-叠氮-D-脯氨酸乙酯,(4S)-1-BOC-4-AZIDO-D-PROLINEETHYLESTER | 132623-06-4

• 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
• 中文名称: (4S)-1-BOC-4-叠氮-D-脯氨酸乙酯,(4S)-1-BOC-4-AZIDO-D-PROLINEETHYLESTER
• 英文名称: (4S)-1-(tert-butoxycarbonyl)-4-azido-D-proline ethyl ester
• 英文别名: (4S)-1-Boc-4-azido-D-proline ethyl ester；1-O-tert-butyl 2-O-ethyl (2R,4S)-4-azidopyrrolidine-1,2-dicarboxylate
• CAS: 132623-06-4
• 化学式: C₁₂H₂₀N₄O₄
• 分子量: 284.315
• InChiKey: JXABBHUZBQZPLX-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S)-1-BOC-4-叠氮-D-脯氨酸乙酯,(4S)-1-BOC-4-AZIDO-D-PROLINEETHYLESTER 在 palladium on activated charcoal sodium hydroxide 、 氨 、 氢气 、 silver nitrate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 22.0 ℃ 、689.48 kPa 条件下， 反应 30.0h， 生成 (4S)-1-(tert-butoxycarbonyl)-4-<<<(p-toluenesulfonyl)imino>aminomethyl>amino>-D-proline
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016
• 作为产物：
  描述：

  N-α-tert-butyloxycarbonyl-cis-4-hydroxy-D-proline ethyl ester 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (4S)-1-BOC-4-叠氮-D-脯氨酸乙酯,(4S)-1-BOC-4-AZIDO-D-PROLINEETHYLESTER
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016

文献信息

• The relationship between physicochemical properties, In vitro activity and pharmacokinetic profiles of analogues of diamine-Containing efflux pump inhibitors
  作者：William J. Watkins、Yakira Landaverry、Roger Léger、Renée Litman、Thomas E. Renau、Nicole Williams、Rose Yen、Jason Z. Zhang、Suzanne Chamberland、Deidre Madsen、David Griffith、Vrushali Tembe、Keith Huie、Michael N. Dudley

  DOI：10.1016/j.bmcl.2003.07.030

  日期：2003.12

  diamine-containing efflux pump inhibitors with respect to in vitro potentiation activity, in vivo stability and acute toxicity, we addressed the question of how to control the pharmacokinetic properties of the series. Upon intravenous administration in the rat, tissue levels of MC-04,124 (the lead compound) were high and prolonged compared to those in the serum. The lipophilicity and basicity of analogues of this

  在体外增强活性，体内稳定性和急性毒性方面优化含二胺的外排泵抑制剂后，我们解决了如何控制该系列药代动力学特性的问题。在大鼠中静脉内给药后，与血清中的组织水平相比，MC-04,124（先导化合物）的组织水平较高且持续时间较长。系统地改变了该化合物类似物的亲脂性和碱性，并探讨了其对药效和药代动力学的影响。在任何检查的活性类似物中，组织与血清中药物水平的比率均未显着降低。
• WEBB, THOMAS R.;EIGENBROT, CHARLES, J. ORG. CHEM., 56,(1991) N, C. 3009-3016
  作者：WEBB, THOMAS R.、EIGENBROT, CHARLES

  DOI：——

  日期：——
• US5120859A
  申请人：——

  公开号：US5120859A

  公开（公告）日：1992-06-09