(4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone | 635313-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone
• 英文别名: (4R,5R)-5-ethenyl-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one
• CAS: 635313-40-5
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: DOFMANRUKKLSMG-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone 在 臭氧 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以76.1%的产率得到(+)-epi-cytoxazone
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181
• 作为产物：
  描述：

  (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 在 sodium tetrahydroborate 、 草酰氯 、 sodium hydride 、 potassium carbonate 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone
  参考文献：
  名称：

  Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone

  摘要：

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

  DOI：

  10.1081/scc-120022181

文献信息

• Oxazolidinone derivatives: Cytoxazone–Linezolid hybrids induces apoptosis and senescence in DU145 prostate cancer cells
  作者：Annavareddi Naresh、Maddimsetti Venkateswara Rao、Sudha Sravanti Kotapalli、Ramesh Ummanni、Batchu Venkateswara Rao

  DOI：10.1016/j.ejmech.2014.04.062

  日期：2014.6

  In this study, we report the synthesis of novel oxazolidinone derivatives derived from linezolid 3 having p-methoxyphenyl group at C-4 position. In vitro evaluation for their anticancer activity toward cultured A549, DU145, HELA, and MCF7 were carried out. The series of compounds prepared displayed wide range of cytotoxicity in MTT assays (10-70 μM) across the cell lines tested. Of the all tested compounds 16 and 17 displayed good anticancer potential against A549 (lung) and DU145 (prostate) cancer cells. Further, to determine their anticancer potential, in the present study we have assessed effect of 17 on DU145 cells growth in in vitro assays. The results clearly demonstrated that the exposure of DU145 cells to 17 inhibits cell proliferation and induces apoptosis by activation of caspase-3 and -9. Long term exposure of DU145 cells to 17 induced cellular senescence confirmed by senescence marker β-galactosidase staining of cells on post exposure to 17. The results from this current report support that the oxazolidinone derivatives with ethyl and acryl substitutions showed promising anticancer activity which will be helpful to develop further novel anticancer agents with better therapeutic potential.
• Stereoselective Synthesis of (−)-Cytoxazone and (+)-5-Epi-cytoxazone
  作者：A. Ravi Kumar、G. Bhaskar、A. Madhan、B. Venkateswara Rao

  DOI：10.1081/scc-120022181

  日期：2003.1.8

  A novel, stereo selective synthesis of (-)-cytoxazone la and stereo-selective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.