3-hexadecanoyltetronic acid | 109517-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3-hexadecanoyltetronic acid
• 英文别名: 4-hydroxy-3-[1-oxohexadecyl]-2(5H)-furanone
• CAS: 109517-13-7
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: YAFHRNIDSKZYCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  24.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  methyl 2-(3-oxo-octadecanoyl)oxyacetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 以5.4 mg的产率得到3-hexadecanoyltetronic acid
  参考文献：
  名称：

  tetronic酸文库的合成侧重于酪氨酸和双重特异性蛋白磷酸酶抑制剂，及其对VHR和cdc25B抑制的评估。

  摘要：

  蛋白质酪氨酸磷酸酶（PTPs）和双特异性磷酸酶（DSPs）的选择性抑制剂有望成为阐明PTPs自身生物学功能的有用工具，并且有望成为新型疗法的候选者。我们计划了一种用于鉴定PTP / DSP抑制剂的文库方法，其中将3-酰基teonic酸用作“核心”磷酸盐模拟物。合成了一系列新颖的tetronic酸衍生物，并评估了其为双特异性蛋白磷酸酶VHR和cdc25B的抑制剂。发现几种化合物是cdc25B的有效抑制剂，cdc25B是细胞周期进程的关键酶。本文所述的有希望的结果有力地表明，该tetronic酸文库作为专注于PTP / DSP选择性抑制剂的文库是有效的。

  DOI：

  10.1021/jm0100741

文献信息

• Tetronic and thiotetronic acid derivatives as phospholipase A.sub.2
  申请人：American Home Products Corporation

  公开号：US05242945A1

  公开（公告）日：1993-09-07

  There are disclosed compounds of the formula: ##STR1## wherein X is --CH.sub.2 R; R is ##STR2## and further when Y=S, R may also be --(CH.sub.2).sub.e CH.sub.3 ; Y is --O--or --S--; R.sup.1 and R.sup.2 are each, independently, hydrogen or lower alkyl; R.sup.3 is indolyl, furyl, phenyl or phenyl optionally mono- or disubstituted independently by alkyl of 1-7 carbon atoms, --C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3, --C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3, haloloweralkyl, perfluoroalkyl, lower alkoxy, aryl alkoxy, halo or nitro; R.sup.4 and R.sup.5 are, independently, --COCH.sub.2 R.sup.7, --CO.sub.2 R.sup.7, --CONHR.sup.7, geranyl or CH.sub.2 R.sup.3 ; R.sup.6 is hydrogen or lower alkyl; R.sup.7 is geranyl and any moiety selected from R other than ##STR3## A and B are, independently, --O--, --S-- or --NR.sup.6 --; and a is 0-8; b is 1-10 when Y=S, and 2-10 when Y=O; c is 1-3; d is 0-9; and e is 3-18; which by virtue of their ability to inhibit PLA.sub.2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals.

  公开了公式为：##STR1##的化合物，其中X为--CH.sub.2 R; R为##STR2##，当Y=S时，R也可以为--(CH.sub.2).sub.e CH.sub.3 ; Y为--O--或--S--; R.sup.1和R.sup.2各自独立地为氢或低碳基; R.sup.3为吲哚基、呋喃基、苯基或苯基，可独立地被1-7碳原子的烷基、--C(CH.sub.3).sub.3、--C(CH.sub.3).sub.2 CH.sub.2 C(CH.sub.3).sub.3、--C(CH.sub.3).sub.2 CH.sub.2 CH.sub.3、卤代低碳基、全氟烷基、低碳基氧、芳基氧、卤基或硝基取代; R.sup.4和R.sup.5独立地为--COCH.sub.2 R.sup.7、--CO.sub.2 R.sup.7、--CONHR.sup.7、香叶醇或CH.sub.2 R.sup.3 ; R.sup.6为氢或低碳基; R.sup.7为香叶醇和除##STR3##以外的任何基团; A和B独立地为--O--、--S--或--NR.sup.6 --; a为0-8; 当Y=S时，b为1-10，当Y=O时，b为2-10; c为1-3; d为0-9; e为3-18; 由于它们具有抑制PLA.sub.2的能力，因此可用作抗炎药物，还公开了一种治疗免疫炎症状况，例如过敏、过敏反应、哮喘和哺乳动物炎症的方法。
• Skin whiteners containing hydroxytetronic acid derivatives
  申请人：——

  公开号：US20020141956A1

  公开（公告）日：2002-10-03

  Skin whitening compositions contain at least one &agr;-hydroxytetronic derivative such as diphenyl hydroxytetronic acid. Some embodiments contain adjunct ingredients that enhance the efficacy and stability of skin whitening formulations such as a tetronic acid derivative that inhibits tyrosinase or tyrosine phosphatase, hydroquinone, an &agr;-hydroxy acid such as glycolic acid, and a fatty acid ester of ascorbic acid such as ascorbyl palmitate.

  美白肌肤的配方含有至少一种α-羟基四酮衍生物，例如二苯基羟基四酮酸。一些实施例包含辅助成分，可增强美白配方的功效和稳定性，例如抑制酪氨酸酶或酪氨酸磷酸酶的四酮酸衍生物、氢醌、α-羟基酸，例如乙酰基甘氨酸和抗坏血酸的脂肪酸酯，例如棕榈酸抗坏血酸。
• Tetronic and thiotetronic acid derivatives
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0508690A1

  公开（公告）日：1992-10-14

  There are disclosed compounds of the formula: wherein    X has specified meanings    Y is -O- or -S-; and    R1 and R2 are each, independently, hydrogen or lower alkyl; which by virtue of their ability to inhibit PLA2, are of use as antiinflammatory agents and there is also disclosed a method for the treatment of immunoinflammatory conditions, such as allergy, anaphylaxis, asthma and inflammation in mammals.

  已公开的化合物式如下 其中 X 具有特定含义 Y 是-O-或-S-；以及 R1和R2各自独立地为氢或低级烷基； 本发明还公开了一种治疗哺乳动物免疫炎症，如过敏、过敏性休克、哮喘和炎症的方法。
• Targeting <i>Staphylococcus aureus</i> Quorum Sensing with Nonpeptidic Small Molecule Inhibitors
  作者：Ewan J. Murray、Rebecca C. Crowley、Alex Truman、Simon R. Clarke、James A. Cottam、Gopal P. Jadhav、Victoria R. Steele、Paul O’Shea、Catharina Lindholm、Alan Cockayne、Siri Ram Chhabra、Weng C. Chan、Paul Williams

  DOI：10.1021/jm500215s

  日期：2014.3.27

  A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.
• Nomura, Keiichi; Hori, Kozo; Arai, Mikio, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 12, p. 5188 - 5191
  作者：Nomura, Keiichi、Hori, Kozo、Arai, Mikio、Yoshii, Eiichi

  DOI：——

  日期：——