5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione | 736177-64-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 736177-64-3
• 化学式: C₁₈H₃₀O₅
• 分子量: 326.433
• InChiKey: OBCDRAOVAZLLBB-UHFFFAOYSA-N

物化性质

• 沸点：
  483.1±45.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (R)-1-methyl-3-oxobutyl 3-oxotetradecanoate
  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
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 月桂酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.33h， 生成 5-(1-hydroxydodecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  具有高对映体纯度的N-酰化-1-高丝氨酸内酯（AHL）群体感应分子的合成的稳健途径

  摘要：

  在以有用方式操纵细菌群体感应系统的方法的开发中，自然群体感应分子和相关结构类似物的现成可用性具有重要的生物学意义。在这封信中，我们报告了合成一系列N-酰化-1-高丝氨酸内酯（AHL）群体感应分子的稳健路线。至关重要的是，我们分析了最终AHL的对映体纯度，并在所有情况下均观察到了极佳的水平。

  DOI：

  10.1016/j.tetlet.2011.04.059

文献信息

• Synthetic libraries of tyrosine-derived bacterial metabolites
  作者：Savvas N. Georgiades、Jon Clardy

  DOI：10.1016/j.bmcl.2007.10.058

  日期：2008.5

  The preparation of a collection of 131 small molecules, reminiscent of families of long chain N-acyl tyrosines, enamides and enol esters that have been isolated from heterologous expression of environmental DNA (eDNA) in Escherichia coli, is reported. The synthetic libraries of N-acyl tyrosines and their 3-keto counterparts were prepared via solid-phase routes, whereas the enamides and enol esters

  据报道，制备了 131 个小分子的集合，让人联想到长链 N-酰基酪氨酸、烯酰胺和烯醇酯家族，这些分子是从大肠杆菌环境 DNA (eDNA) 的异源表达中分离出来的。N-酰基酪氨酸及其3-酮对应物的合成库是通过固相途径制备的，而烯酰胺和烯醇酯是在溶液相中合成的。
• The Ras Pathway Modulator Melophlin A Targets Dynamins
  作者：Tanja Knoth、Karin Warburg、Catherine Katzka、Amrita Rai、Alexander Wolf、Andreas Brockmeyer、Petra Janning、Thomas F. Reubold、Susanne Eschenburg、Dietmar J. Manstein、Katja Hübel、Markus Kaiser、Herbert Waldmann

  DOI：10.1002/anie.200902023

  日期：2009.9.14

  combination of organic synthesis, chemical proteomics, biophysics, and cell and molecular biology investigations reveals that the natural product melophlin A (purple) influences signal propagation through the Ras network by interfering with the function of dynamins (green) in endocytosis.

  天然原因：有机合成，化学蛋白质组学，生物物理学以及细胞和分子生物学研究的结合表明，天然产物melophlin A（紫色）通过干扰细胞活力（绿色）在胞吞作用中影响通过Ras网络传播的信号。
• Synthesis of β-ketoesters from renewable resources and Meldrum's acid
  作者：Rafael C. Brinkerhoff、Hernan F. Tarazona、Patrick M. de Oliveira、Darlene C. Flores、Caroline Da R. Montes D'Oca、Dennis Russowsky、Marcelo G. Montes D'Oca

  DOI：10.1039/c4ra08986c

  日期：——

  β-Ketoesters are valuable building blocks for the synthesis of compounds with different biological activities.

  β-酮酯是合成具有不同生物活性化合物的宝贵构建模块。
• Synthetic Analogues of the Bacterial Signal (Quorum Sensing) Molecule <i>N</i>-(3-Oxododecanoyl)-<scp>l</scp>-homoserine Lactone as Immune Modulators
  作者：Siri Ram Chhabra、Chris Harty、Doreen S. W. Hooi、Mavis Daykin、Paul Williams、Gary Telford、David I. Pritchard、Barrie W. Bycroft

  DOI：10.1021/jm020909n

  日期：2003.1.1

  Comparative immune modulatory activity for a range of synthetic analogues of a Pseudomonas aeruginosa signal molecule, N-(3-oxododecanoyl)-L-homoserine lactone (3O, C-12-HSL), is described. Twenty-four single or combination systematic alterations of the structural components of 3O, C12-HSL were introduced as described. Given the already defined immunological profile of the parent compound, 3O, C12-HSL, these compounds were assayed for their ability to inhibit murine and human leucocyte proliferation and TNF-alpha secretion by lipopolysaccharide (LPS) stimulated human leucocytes in order to provide an initial structure-activity profile. From IC50 values obtained with a murine splenocyte proliferation assay, it is apparent that acylated L-homoserine lactones with an 11-13 C side chain containing either a 3-oxo or a 3-hydroxy group are optimal structures for immune suppressive activity. These derivatives of 3O, C-12-HSL with monounsaturation and/or a terminal nonpolar substituent on the side chain were also potent immune suppressive agents. However, structures lacking the homoserine lactone ring, structures lacking the L-configuration at the chiral center, and those with polar substituents were essentially devoid of activity. The ability of compounds selected from the optimal activity range to modulate mitogen-driven human peripheral blood mononuclear cell proliferation and LPS-induced TNF-alpha secretion indicates the suitability of these compounds for further investigation in relation to their molecular mechanisms of action in TNF-alpha driven immunological diseases, particularly autoimmune diseases such as psoriasis, rheumatoid arthritis, and type 1 (autoimmune) diabetes.