benzyl (2R)-2-(3-aminopropanoyloxy)-4-methylpentanoate | 697217-20-2

• 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: benzyl (2R)-2-(3-aminopropanoyloxy)-4-methylpentanoate
• CAS: 697217-20-2
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: RRKVZVMWCIXYOC-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl (2R)-2-(3-aminopropanoyloxy)-4-methylpentanoate 在 palladium dihydroxide 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 22.5h， 生成 tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate
  参考文献：
  名称：

  Total Synthesis and Anti-Tubulin Activity of Epi-C3 Analogues of Cryptophycin-24

  摘要：

  Epi-C3-cryptophycin-24, epi-C3-m-chlorobenzyl-cryptophycin-24, and the corresponding styrenes were synthesized and tested in vitro against the MCF-7 and multidrug-resistant MCF-7/ADR breast cancer cell lines and in an in vitro tubulin assembly assay. The results demonstrate that the S configuration at the C3 stereocenter is not required to induce potent cytotoxicity and the m-Cl substituent present on the C10 side chain did not induce any large change in activity.

  DOI：

  10.1021/jm030555f
• 作为产物：
  描述：

  (R)-2-羟基-4-甲基戊酸 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 benzyl (2R)-2-(3-aminopropanoyloxy)-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis and Anti-Tubulin Activity of Epi-C3 Analogues of Cryptophycin-24

  摘要：

  Epi-C3-cryptophycin-24, epi-C3-m-chlorobenzyl-cryptophycin-24, and the corresponding styrenes were synthesized and tested in vitro against the MCF-7 and multidrug-resistant MCF-7/ADR breast cancer cell lines and in an in vitro tubulin assembly assay. The results demonstrate that the S configuration at the C3 stereocenter is not required to induce potent cytotoxicity and the m-Cl substituent present on the C10 side chain did not induce any large change in activity.

  DOI：

  10.1021/jm030555f

文献信息

• Total Synthesis and Anti-Tubulin Activity of Epi-C3 Analogues of Cryptophycin-24
  作者：Suzanne B. Buck、Jacquelyn K. Huff、Richard H. Himes、Gunda I. Georg

  DOI：10.1021/jm030555f

  日期：2004.7.1

  Epi-C3-cryptophycin-24, epi-C3-m-chlorobenzyl-cryptophycin-24, and the corresponding styrenes were synthesized and tested in vitro against the MCF-7 and multidrug-resistant MCF-7/ADR breast cancer cell lines and in an in vitro tubulin assembly assay. The results demonstrate that the S configuration at the C3 stereocenter is not required to induce potent cytotoxicity and the m-Cl substituent present on the C10 side chain did not induce any large change in activity.