(S)-3-[(E)-dodec-12-enoyl]-5,6-dihydro-4,6-dimethyl-2H-pyran-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (S)-3-[(E)-dodec-12-enoyl]-5,6-dihydro-4,6-dimethyl-2H-pyran-2-one
• 英文别名: dictyopyrone A；(2S)-5-[(E)-dodec-10-enoyl]-2,4-dimethyl-2,3-dihydropyran-6-one
• 化学式: C₁₉H₃₀O₃
• 分子量: 306.445
• InChiKey: LDTOSUNDGREUIH-APHBUQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,10-癸二醇 在 盐酸 、 4-二甲氨基吡啶 、 重铬酸吡啶 、 pyridine-SO3 complex 、 sodium ethanolate 、 sodium hydride 、 二异丁基氢化铝 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 71.0h， 生成 (S)-3-[(E)-dodec-12-enoyl]-5,6-dihydro-4,6-dimethyl-2H-pyran-2-one
  参考文献：
  名称：

  Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity

  摘要：

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.001

文献信息

• Novel Acyl α-Pyronoids, Dictyopyrone A, B, and C, from <i>Dictyostelium</i> Cellular Slime Molds
  作者：Yoshiaki Takaya、Haruhisa Kikuchi、Yuichi Terui、Jun Komiya、Ken-Ichi Furukawa、Kazuhiko Seya、Shigeru Motomura、Akira Ito、Yoshiteru Oshima

  DOI：10.1021/jo991338i

  日期：2000.2.1

  three novel compounds, dictyopyrone A (1) and B (2) from D. discoideum and D. rhizoposium and dictyopyrone C (3) from D. longosporum. They possess a unique alpha-pyrone moiety with a side chain at the C-3 position. Their relative structures were elucidated by spectral means, and the absolute configuration was confirmed by asymmetric synthesis of 1. Since these compounds were obtained from different

  为了阐明Dictyostelium细胞粘液霉菌次生代谢产物的多样性，我们研究了三种粘液霉菌的成分。从其子实体的甲醇提取物中，我们获得了三种新颖的化合物：D。discoideum和D. rhizoposium的dictyopyrone A（1）和B（2）和L. longosporum的dictyopyrone C（3）。它们具有在C-3位置带有侧链的独特的α-吡喃酮部分。通过光谱方法阐明了它们的相对结构，并通过1的不对称合成证实了其绝对构型。由于这些化合物是从不同种类的Dictyostelium粘液霉菌中获得的，因此它们可能是该属的一种常见化合物。
• Structural requirements of dictyopyrones isolated from Dictyostelium spp. in the regulation of Dictyostelium development and in anti-leukemic activity
  作者：Haruhisa Kikuchi、Kazunori Sasaki、Jun'ichi Sekiya、Yasuo Maeda、Aiko Amagai、Yuzuru Kubohara、Yoshiteru Oshima

  DOI：10.1016/j.bmc.2004.04.001

  日期：2004.6

  Cellular slime molds are fascinating to the field of developmental biology, and have long been used as excellent model organisms for the study of various aspects of multicellular development. We have recently isolated alpha-pyronoids, named dictyopyrones A-D (1-4), from various species of Dictyostelium cellular slime molds, and it was shown that compound 3 may regulate Dictyostelium development. In this study, we synthesized dictyopyrones A-D (1-4) and their analogues, investigated the physiological role of the molecules in cell growth and morphogenesis in D. discoideum, and further verified their effects on human leukemia K562 cells. Nitrogen-containing compounds 22 and 37 strongly inhibited cell growth in K562 leukemia cells, indicating that these compounds may be utilized as novel lead compounds for anti-leukemic agents. (C) 2004 Elsevier Ltd. All rights reserved.