N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester | 742102-95-0

• 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: N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester
• 英文别名: methyl (2S)-4-methyl-2-[[(2S,3S,6R)-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-phenylmethoxyoxane-2-carbonyl]amino]pentanoate
• CAS: 742102-95-0
• 化学式: C₂₆H₄₀N₂O₇
• 分子量: 492.613
• InChiKey: KXMQVBRVMYRQIY-MLNNCEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 异丙硫醇 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[(1R)-1-{(N-(S-(tert-butyl)sulfanyl)-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-cysteinyl)aminomethyl}-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q
• 作为产物：
  描述：

  2,3-dideoxy-4-O-benzyl-6-O-triphenylmethyl-1-{N-[(tert-butyloxycarbonyl)amino]methyl}-β-D-glucopyranose 在 ruthenium trichloride 、 氢氧化钾 、 dipotassium peroxodisulfate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 N-[(1R)-1-({N-[(tert-butoxy)carbonyl]amino}methyl)-1,2,3-trideoxy-4-benzyloxy-6-oxo-D-arabino-hexopyranos-6-yl]-L-leucine methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Su- gar Amino Acid Based Inhibitors of Pro- tein Prenyl Transferases PFT and PGGT-1

  摘要：

  Eleven analogues of the C-terminal Ca(1)a(2)X Motif found in natural substrates of the prenyl transferases PFT and PGGT-1 were synthesized and evaluated for their inhibition potency and selectivity against PFT and PGGT-1. Replacement of the central dipeptide part a(1)a(2) by a benzylated sugar amino acid resulted in a good and highly selective PFT inhibitor (8, IC50 = 250 +/- 20 nM). The methyl ester of 8 (13) selectively inhibited protein farnesylation in cultured cells.

  DOI：

  10.1021/jm049927q