5-[(tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-[(tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone
• 英文别名: [2-(hydroxymethyl)-5-oxooxolan-2-yl]methyl tetradecanoate
• 化学式: C₂₀H₃₆O₅
• 分子量: 356.503
• InChiKey: IJBRVCLEYDEESF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  (Z,Z)-9,12-十八烷二烯酸二聚物 、 5-[(tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone 在 三甲基乙酰氯 、 三乙胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以54.2%的产率得到
  参考文献：
  名称：

  DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT

  摘要：

  本发明揭示了一种新颖的二酰甘油内酯化合物，用于通过促进中性粒细胞运动来提高免疫力和抑制感染，以及其制备方法和包含该化合物作为活性成分的免疫刺激剂。该二酰甘油内酯化合物由规范中的化学式1表示。在化学式1中，R1和R2分别为N和独立的C2-30脂肪酸基团。

  公开号：

  US20210002242A1
• 作为产物：
  描述：

  5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one 在 三甲基乙酰氯 、 三氯化硼 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 5-[(tetradecanoyloxy)methyl]-5-hydroxymethyl-tetrahydro-2-furanone
  参考文献：
  名称：

  DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT

  摘要：

  本发明揭示了一种新颖的二酰甘油内酯化合物，用于通过促进中性粒细胞运动来提高免疫力和抑制感染，以及其制备方法和包含该化合物作为活性成分的免疫刺激剂。该二酰甘油内酯化合物由规范中的化学式1表示。在化学式1中，R1和R2分别为N和独立的C2-30脂肪酸基团。

  公开号：

  US20210002242A1

文献信息

• Conformationally constrained diacylglycerol analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05874464A1

  公开（公告）日：1999-02-23

  Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.

  构象限制的二酰基甘油类似物、包含这种类似物的制药组合物，以及使用这种类似物作为蛋白激酶C的激动剂和拮抗剂的方法。
• Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template
  作者：Rajiv Sharma、Jeewoo Lee、Shaomeng Wang、George W. A. Milne、Nancy E. Lewin、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm950276v

  日期：1996.1.1

  5,5-Bis(hydroxymethyl)tetrahydro-2-furanone and its isomer 4,4-bis(hydroxymethyl)tetrahydro-2-furanone were investigated as possible templates for the construction of conformationally constrained analogues of the biologically important second messenger, diacylglycerol (DAG). The former lactone contains embedded within its structure an exact glycerol moiety, while in the latter the ring oxygen has been transposed to the other side of the carbonyl group. Al target compounds were synthesized as racemates from 1,3-dihydroxy-2-propanone. The 5,5-bis(hydroxymethyl)tetrahydro-2-furanone proved to be the better template for the construction of DAG surrogates that were demonstrated to have high binding affinities for the biological target, protein kinase C (PK-C). The simplest target compounds derived from this template (3e and 3f) have one of the hydroxyl moieties functionalized either as a myristate or as an oleate ester. The simplest target compound (9e) derived from the ineffective 4,4-bis(hydroxymethyl)tetrahydro-2-furanone template was investigated only with a myristoyl acyl chain. Reducing the long acyl chain to an acetyl moiety and attaching a compensating lipophilic chain to the lactone ring as an alpha-alkylidene moiety produced compounds 10e and 10f(Z-isomers) and 11e and 11f(E-isomers), which were constructed on the more effective 5,5-bis(hydroxymethyl)tetrahydro-2-furanone template. Targets 14c (Z-isomer) and 15c (E-isomer) were derived, in turn, from 4,4-bis(hydroxymethyl)tetrahydro-2-furan. The affinities of these ligands for PK-C were assessed in terms of their ability to displace bound [H-3-20]phorbol 12,13-dibutyrate (PDBU) from the single isozyme PK-C alpha. The biological data support the hypothesis that the increase in binding affinity for PK-C shown by some of these constrained DAG mimetics appears to be entropic in nature. Two of the designed ligands (10e and 10f) showed the highest affinities (34 and 24 nM, respectively) reported so far for a DAG analogue. Assuming that the interaction between these racemic compounds and PK-C is stereospecific, the potency of the active enantiomer is anticipated to double.
• US5874464A
  申请人：——

  公开号：US5874464A

  公开（公告）日：1999-02-23
• [EN] PROTEIN KINASE C INHIBITOR, RELATED COMPOSITION, AND METHOD OF USE<br/>[FR] INHIBITEUR DE LA PROTEINE KINASE, COMPOSITION CONNEXE ET METHODE D'UTILISATION
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2004078118A2

  公开（公告）日：2004-09-16

  Compounds of the formula (1), (2), (3), (4), (5) or (6) or a pharmaceutically acceptable salt thereof, wherein A is a DAG receptor-binding moiety, L is a linker moiety, and B is a zinc finger reactive moiety, and, a pharmaceutical composition comprising an above compound, and methods of use.
• DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT
  申请人：ENZYCHEM LIFESCIENCES CORPORATION

  公开号：US20210002242A1

  公开（公告）日：2021-01-07

  Disclosed are a novel diacylglycerol lactone compound for improving immunity and inhibiting infection by promoting neutrophil movement, a preparation method therefor, and an immunostimulator containing same as an active ingredient. The diacyloglycerol lactone compound is represented by chemical formula 1 of the specification. In chemical formula 1, R1 and R2 are respectively N and independently a C2-30 fatty acid group.

  本发明揭示了一种新颖的二酰甘油内酯化合物，用于通过促进中性粒细胞运动来提高免疫力和抑制感染，以及其制备方法和包含该化合物作为活性成分的免疫刺激剂。该二酰甘油内酯化合物由规范中的化学式1表示。在化学式1中，R1和R2分别为N和独立的C2-30脂肪酸基团。