(2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(phenyl)propionylamino]propionyloxy]-4-methylpentanoic acid | 654068-61-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(phenyl)propionylamino]propionyloxy]-4-methylpentanoic acid
• CAS: 654068-61-8
• 化学式: C₂₃H₃₄N₂O₇
• 分子量: 450.532
• InChiKey: VGFQOWUZXPHGDI-MSOLQXFVSA-N

物化性质

• 沸点：
  668.8±55.0 °C(predicted)
• 密度：
  1.163±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131.03
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(phenyl)propionylamino]propionyloxy]-4-methylpentanoic acid 在 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2E,7E)-(5S,6R)-5-{(S)-2-[3-((R)-2-Amino-3-phenyl-propionylamino)-propionyloxy]-4-methyl-pentanoyloxy}-6-methyl-8-phenyl-octa-2,7-dienoic acid; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Total Synthesis and Antitubulin Activity of C10 Analogues of Cryptophycin-24

  摘要：

  The unsubstituted, 3'-C1, 4'-C1, and 3',4'-diC1 C10 analogues of cryptophycin-24 were prepared via total synthesis and tested in vitro for cytotoxicity against MCF-7 and multi-drug-resistant MCF-7/ADR breast cancer cell lines and in a tubulin assembly assay. The ED50 values ranged from 7.2 to 15.8 muM in the tubulin assay and from 0.05 to 3.4 nM in the cell assays. The presence of a 3'-C1 and/or 4'-C1 substituent on the C10 phenyl ring increased cytotoxicity in the MCF-7 cell line compared to the unsubstituted phenyl ring. The most potent compound in this series possessed a X-Cl substituent on the C10 phenyl ring. The X-Cl analogue had ED50 values of 50 and 580 pM in the MCF-7 and MCF-7/ADR cell lines, respectively. Its activity was very similar to the parent compound cryptophycin-24. Substitution of the 4'-MeO group in cryptophycin-24 with a 4'-C1 moiety did not significantly affect cytotoxicity against MCF-7 and MCF-7/ADR cells compared to the parent compound. These results demonstrated that the 4'-MeO group in cryptophycin-24 is not essential and can be replaced with X-Cl or 4'-C1 substituents.

  DOI：

  10.1021/jm030278c
• 作为产物：
  描述：

  benzyl (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(phenyl)propionylamino]propionyloxy]-4-methylpentanoate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 (2S)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(phenyl)propionylamino]propionyloxy]-4-methylpentanoic acid
  参考文献：
  名称：

  Total Synthesis and Antitubulin Activity of C10 Analogues of Cryptophycin-24

  摘要：

  The unsubstituted, 3'-C1, 4'-C1, and 3',4'-diC1 C10 analogues of cryptophycin-24 were prepared via total synthesis and tested in vitro for cytotoxicity against MCF-7 and multi-drug-resistant MCF-7/ADR breast cancer cell lines and in a tubulin assembly assay. The ED50 values ranged from 7.2 to 15.8 muM in the tubulin assay and from 0.05 to 3.4 nM in the cell assays. The presence of a 3'-C1 and/or 4'-C1 substituent on the C10 phenyl ring increased cytotoxicity in the MCF-7 cell line compared to the unsubstituted phenyl ring. The most potent compound in this series possessed a X-Cl substituent on the C10 phenyl ring. The X-Cl analogue had ED50 values of 50 and 580 pM in the MCF-7 and MCF-7/ADR cell lines, respectively. Its activity was very similar to the parent compound cryptophycin-24. Substitution of the 4'-MeO group in cryptophycin-24 with a 4'-C1 moiety did not significantly affect cytotoxicity against MCF-7 and MCF-7/ADR cells compared to the parent compound. These results demonstrated that the 4'-MeO group in cryptophycin-24 is not essential and can be replaced with X-Cl or 4'-C1 substituents.

  DOI：

  10.1021/jm030278c