(4R,5S,2'S,3'R,4'E)-3-(2',4'-dimethyl-3'-hydroxy-1'-oxo-4'-hexenyl)-4-methyl-5-phenyl-2-oxazolidinone | 760984-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R,5S,2'S,3'R,4'E)-3-(2',4'-dimethyl-3'-hydroxy-1'-oxo-4'-hexenyl)-4-methyl-5-phenyl-2-oxazolidinone
• 英文别名: (4R,5S)-3-[(E,2S,3R)-3-hydroxy-2,4-dimethylhex-4-enoyl]-4-methyl-5-phenyl-1,3-oxazolidin-2-one
• CAS: 760984-68-7
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: UXOPVZQGQPPOIX-SHPLYALYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S,2'S,3'R,4'E)-3-(2',4'-dimethyl-3'-hydroxy-1'-oxo-4'-hexenyl)-4-methyl-5-phenyl-2-oxazolidinone 在 咪唑 、 lithium aluminium tetrahydride 、 三甲基铝 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2S,3R,4E)-3-(tert-Butyldimethylsiloxy)-2,4-dimethylhex-4-en-1-al
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 、 (4R,5S)-3-丙酰基-4-甲基-5-苯基-2-噁唑烷酮 在 三氟甲磺酸二丁硼 、 N,N-二异丙基乙胺 、 双氧水 作用下， 以 二氯甲烷 、 甲醇 、 phosphate buffer 为溶剂， 反应 3.5h， 以60%的产率得到(4R,5S,2'S,3'R,4'E)-3-(2',4'-dimethyl-3'-hydroxy-1'-oxo-4'-hexenyl)-4-methyl-5-phenyl-2-oxazolidinone
  参考文献：
  名称：

  Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk Philinopsis speciosa

  摘要：

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.

  DOI：

  10.1021/np049949f

文献信息

• EVANS, D. A.;MORRISSEY, M. M., TETRAHEDRON LETT., 1984, 25, N 41, 4637-4640
  作者：EVANS, D. A.、MORRISSEY, M. M.

  DOI：——

  日期：——
• Kulokekahilide-2, a Cytotoxic Depsipeptide from a Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Yoichi Nakao、Wesley Y. Yoshida、Yuuki Takada、Junji Kimura、Liu Yang、Susan L. Mooberry、Paul J. Scheuer

  DOI：10.1021/np049949f

  日期：2004.8.1

  A cytotoxic depsipeptide, kulokekahilide-2 (1), was isolated from a cephalaspidean mollusk, Philinopsis speciosa. The structure elucidation of kulokekahilide-2 was carried out by spectroscopic analysis and chemical degradation. Kulokekahilide-2 showed potent cytotoxicity against several cell lines (P388, SKOV-3, MDA-MB-435, and A-10 with IC50 values ranging from 4.2 to 59.1 nM) indicating cancer cell selectivity.