(9H-fluoren-9-yl)methyl (2S,3S)-1-((R)-1-hydroxy-3-phenylpropan-2-ylamino)-3-methyl-1-oxopentan-2-ylcarbamate | 851539-19-0

• 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: (9H-fluoren-9-yl)methyl (2S,3S)-1-((R)-1-hydroxy-3-phenylpropan-2-ylamino)-3-methyl-1-oxopentan-2-ylcarbamate
• 英文别名: Fmoc-NH-L-Ile-D-Phe-CH2OH；9H-fluoren-9-ylmethyl N-[(2S,3S)-1-[[(2R)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]carbamate
• CAS: 851539-19-0
• 化学式: C₃₀H₃₄N₂O₄
• 分子量: 486.611
• InChiKey: FZGWXAYQJDULNU-PGKWVRKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (9H-fluoren-9-yl)methyl (2S,3S)-1-((R)-1-hydroxy-3-phenylpropan-2-ylamino)-3-methyl-1-oxopentan-2-ylcarbamate 、 乙酸酐 在 吡啶 作用下， 反应 1.0h， 生成 [(2R)-2-[[(2S,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylpentanoyl]amino]-3-phenylpropyl] acetate
  参考文献：
  名称：

  Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

  摘要：

  Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9,12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8+/-0.1 and 1.7+/-0.6 mu M, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead antiinflammatory agents. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.008
• 作为产物：
  描述：

  D-苯丙氨醇 、 Fmoc-L-异亮氨酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (9H-fluoren-9-yl)methyl (2S,3S)-1-((R)-1-hydroxy-3-phenylpropan-2-ylamino)-3-methyl-1-oxopentan-2-ylcarbamate
  参考文献：
  名称：

  Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

  摘要：

  Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9,12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8+/-0.1 and 1.7+/-0.6 mu M, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead antiinflammatory agents. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.11.008

文献信息

• Rapamycin peptides conjugates: synthesis and uses thereof
  申请人：Sharma K. Sanjay

  公开号：US20070129394A1

  公开（公告）日：2007-06-07

  The present invention relates to new rapamycin derivatives for the inhibition of cell proliferation. The compounds can advantageously target two proteins in dividing cells and interfere with cell cycle. There is thus provided derivatives of rapamycin in which the 42 position of rapamycin is linked to an amino acid or a peptide through a carbamate ester linkage. These rapamycin derivatives can be synthesized by reacting 42-O-(4-Nitrophenoxycarbonyl) rapamycin and an amino acid or a free amino peptide under basic conditions. These rapamycin derivatives can be used to inhibit the cell cycle and are therefore useful for treating cell proliferation disorders.

  本发明涉及新的雷帕霉素衍生物，用于抑制细胞增殖。这些化合物可以有利地靶向分裂细胞中的两种蛋白质并干扰细胞周期。因此提供了雷帕霉素衍生物，其中雷帕霉素的42位通过氨基酸或肽的氨基甲酸酯键连接。这些雷帕霉素衍生物可以通过在碱性条件下反应42-O-(4-硝基苯氧羰基)雷帕霉素和氨基酸或自由氨基肽来合成。这些雷帕霉素衍生物可以用于抑制细胞周期，因此对于治疗细胞增殖性疾病非常有用。