5-methyl-5-(4-methylpent-3-enyl)-1-oxo[1,2]dithiolan-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 5-methyl-5-(4-methylpent-3-enyl)-1-oxo[1,2]dithiolan-3-one
• 英文别名: 5-Methyl-5-(4-methylpent-3-enyl)-1-oxodithiolan-3-one；5-methyl-5-(4-methylpent-3-enyl)-1-oxodithiolan-3-one
• 化学式: C₁₀H₁₆O₂S₂
• 分子量: 232.368
• InChiKey: RGWHSIQSKPWUMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-5-(4-methylpent-3-enyl)-1-oxo[1,2]dithiolan-3-one 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 3.0h， 生成 3-ethyldisulfanyl-3,7-dimethyloct-6-enoic acid methyl ester
  参考文献：
  名称：

  Synthesis and characterization of a small analogue of the anticancer natural product leinamycin

  摘要：

  Leinamycin (1) is a Streptomyces-derived natural product that displays nanomolar IC50 values against human cancer cell lines. In the work described here, we report the synthesis and characterization of a small leinamycin analogue 19 that closely resembles the 'upper-right quadrant' of the natural product, consisting of an alicyclic 1,2-dithiolan-3-one 1-oxide heterocycle connected to an alkene by a two-carbon linker. The results indicate that this small analogue contains the core set of functional groups required to enable thiol-triggered generation of both redox active polysulfides and an episulfonium ion intermediate via the complex reaction cascade first seen in the natural product leinamycin. The small leinamycin analogue 19 caused thiol-triggered oxidative DNA strand cleavage in a manner similar to the natural product, but did not alkyate duplex DNA effectively. This highlights the central role of the 18-membered macrocycle of leinamycin in driving efficient DNA alkylation by the natural product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.021
• 作为产物：
  描述：

  香叶酸 在 哌啶 、 4-二甲氨基吡啶 、 硫化氢 、 氨 、 sodium 、 二甲基二环氧乙烷 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 四氯化碳 、 丙酮 为溶剂， 反应 75.0h， 生成 5-methyl-5-(4-methylpent-3-enyl)-1-oxo[1,2]dithiolan-3-one
  参考文献：
  名称：

  Synthesis and characterization of a small analogue of the anticancer natural product leinamycin

  摘要：

  Leinamycin (1) is a Streptomyces-derived natural product that displays nanomolar IC50 values against human cancer cell lines. In the work described here, we report the synthesis and characterization of a small leinamycin analogue 19 that closely resembles the 'upper-right quadrant' of the natural product, consisting of an alicyclic 1,2-dithiolan-3-one 1-oxide heterocycle connected to an alkene by a two-carbon linker. The results indicate that this small analogue contains the core set of functional groups required to enable thiol-triggered generation of both redox active polysulfides and an episulfonium ion intermediate via the complex reaction cascade first seen in the natural product leinamycin. The small leinamycin analogue 19 caused thiol-triggered oxidative DNA strand cleavage in a manner similar to the natural product, but did not alkyate duplex DNA effectively. This highlights the central role of the 18-membered macrocycle of leinamycin in driving efficient DNA alkylation by the natural product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.021

文献信息

• Synthesis and characterization of a small analogue of the anticancer natural product leinamycin
  作者：Kripa Keerthi、Anuruddha Rajapakse、Daekyu Sun、Kent S. Gates

  DOI：10.1016/j.bmc.2012.10.021

  日期：2013.1

  Leinamycin (1) is a Streptomyces-derived natural product that displays nanomolar IC50 values against human cancer cell lines. In the work described here, we report the synthesis and characterization of a small leinamycin analogue 19 that closely resembles the 'upper-right quadrant' of the natural product, consisting of an alicyclic 1,2-dithiolan-3-one 1-oxide heterocycle connected to an alkene by a two-carbon linker. The results indicate that this small analogue contains the core set of functional groups required to enable thiol-triggered generation of both redox active polysulfides and an episulfonium ion intermediate via the complex reaction cascade first seen in the natural product leinamycin. The small leinamycin analogue 19 caused thiol-triggered oxidative DNA strand cleavage in a manner similar to the natural product, but did not alkyate duplex DNA effectively. This highlights the central role of the 18-membered macrocycle of leinamycin in driving efficient DNA alkylation by the natural product. (C) 2012 Elsevier Ltd. All rights reserved.