3-decanoyltetronic acid | 145436-96-0

• 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-decanoyltetronic acid
• 英文别名: 4-hydroxy-3-(1-oxodecyl)-2(5H)-furanone
• CAS: 145436-96-0
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: KRYBBZCRSUICMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  18.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  4-羟乙酰乙酸内酯 、 正癸酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以15%的产率得到3-decanoyltetronic acid
  参考文献：
  名称：

  Targeting Staphylococcus aureus Quorum Sensing with Nonpeptidic Small Molecule Inhibitors

  摘要：

  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.

  DOI：

  10.1021/jm500215s

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.

  公开了以下式的化合物：## STR1 ##其中X为-CH.sub.2 R; R为## STR2 ##并且当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分别独立地为氢或低碳基; R.sup.3为吲哚基，呋喃基，苯基或苯基，可以单独或双独立地被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，低碳烷氧基，芳基烷氧基，卤素或硝基取代; R.sup.4和R.sup.5分别独立地为-COCH.sub.2 R.sup.7，-CO.sub.2 R.sup.7，-CONHR.sup.7，蒎烯基或CH.sub.2 R.sup.3; R.sup.6为氢或低碳基; R.sup.7为蒎烯基和除## STR3 ##之外的任何基团; A和B分别为-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;由于它们能够抑制PLA.sub.2，因此可用作抗炎药物，还公开了一种用于治疗免疫炎症疾病，如过敏，过敏反应，哮喘和哺乳动物炎症的方法。
• 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。
• US5242945A
  申请人：——

  公开号：US5242945A

  公开（公告）日：1993-09-07