(R)-methyl 6-(N-(benzyloxy)formamido)-2-(2-(2-hydroxyphenyl)-5-methyloxazole-4-carboxamido)hexanoate | 937244-48-9

• 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: (R)-methyl 6-(N-(benzyloxy)formamido)-2-(2-(2-hydroxyphenyl)-5-methyloxazole-4-carboxamido)hexanoate
• 英文别名: methyl (2R)-6-[formyl(phenylmethoxy)amino]-2-[[2-(2-hydroxyphenyl)-5-methyl-1,3-oxazole-4-carbonyl]amino]hexanoate
• CAS: 937244-48-9
• 化学式: C₂₆H₂₉N₃O₇
• 分子量: 495.532
• InChiKey: HLMAOSDIWGTPLW-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-methyl 6-(N-(benzyloxy)formamido)-2-(2-(2-hydroxyphenyl)-5-methyloxazole-4-carboxamido)hexanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 以89%的产率得到(R)-methyl 6-(N-(hydroxy)formamido)-2-(2-(2-hydroxyphenyl)-5-methyloxazole-4-carboxamido)hexanoate
  参考文献：
  名称：

  Syntheses of Amamistatin Fragments and Determination of Their HDAC and Antitumor Activity

  摘要：

  Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC(50) 0.24-0.56 mu M). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition mediated by the N-formyl-N-hydroxy lysine moiety. Amamistatin B fragment analogs were synthesized and screened for biological activity. These compounds were modest HDAC inhibitors and showed antitumor activity against MCF-7 and PC-3 human tumor cells.

  DOI：

  10.1021/ol070382e
• 作为产物：
  描述：

  methyl (2R)-2-(benzyloxycarbonylamino)-6-(N-(phenylcarbonyloxy)formamido)hexanoate 在 氢溴酸 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 63.5h， 生成 (R)-methyl 6-(N-(benzyloxy)formamido)-2-(2-(2-hydroxyphenyl)-5-methyloxazole-4-carboxamido)hexanoate
  参考文献：
  名称：

  Syntheses of Amamistatin Fragments and Determination of Their HDAC and Antitumor Activity

  摘要：

  Amamistatins A and B are natural products found to have anti-proliferative effects against MCF-7, A549, and MKN45 human tumor cell lines (IC(50) 0.24-0.56 mu M). It was proposed that their activity was due to histone deacetylase (HDAC) inhibition mediated by the N-formyl-N-hydroxy lysine moiety. Amamistatin B fragment analogs were synthesized and screened for biological activity. These compounds were modest HDAC inhibitors and showed antitumor activity against MCF-7 and PC-3 human tumor cells.

  DOI：

  10.1021/ol070382e