methyl (2S)-2-[[8-(hydroxyamino)-8-oxooctanoyl]amino]-3-(4-thiophen-2-ylphenyl)propanoate | 1019684-33-3

• 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: methyl (2S)-2-[[8-(hydroxyamino)-8-oxooctanoyl]amino]-3-(4-thiophen-2-ylphenyl)propanoate
• CAS: 1019684-33-3
• 化学式: C₂₂H₂₈N₂O₅S
• 分子量: 432.541
• InChiKey: BKOVMQQMYVHKLB-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-3-(4-(thiophen-2-yl)phenyl)-2-(7-trityloxycarbamoylheptanoylamino)propionic acid methyl ester 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以55%的产率得到methyl (2S)-2-[[8-(hydroxyamino)-8-oxooctanoyl]amino]-3-(4-thiophen-2-ylphenyl)propanoate
  参考文献：
  名称：

  Phenylalanine-containing hydroxamic acids as selective inhibitors of class IIb histone deacetylases (HDACs)

  摘要：

  We synthesized biarylalanine-containing hydroxamic acids and tested them on immunoprecipitated HDAC1 and HDAC6 and show a subtype selectivity for HDAC6 that was confirmed in cells by Western blot (tubulin vs histones). We obtained an X-ray structure with a HDAC6-selective inhibitor with the bacterial deacetylase HDAH. Docking studies were carried out using HDAC1 and HDAC6 protein models. Antiproliferative activity was shown on cancer cells for selected compounds.

  DOI：

  10.1016/j.bmc.2007.10.092

文献信息

• Phenylalanine-containing hydroxamic acids as selective inhibitors of class IIb histone deacetylases (HDACs)
  作者：Stefan Schäfer、Laura Saunders、Elena Eliseeva、Alfredo Velena、Mira Jung、Andreas Schwienhorst、Anja Strasser、Achim Dickmanns、Ralf Ficner、Sonja Schlimme

  DOI：10.1016/j.bmc.2007.10.092

  日期：2008.2.15

  We synthesized biarylalanine-containing hydroxamic acids and tested them on immunoprecipitated HDAC1 and HDAC6 and show a subtype selectivity for HDAC6 that was confirmed in cells by Western blot (tubulin vs histones). We obtained an X-ray structure with a HDAC6-selective inhibitor with the bacterial deacetylase HDAH. Docking studies were carried out using HDAC1 and HDAC6 protein models. Antiproliferative activity was shown on cancer cells for selected compounds.