5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one | 862549-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one
• 英文别名: 5-(Hydroxymethyl)-5-(phenylmethoxymethyl)oxolan-2-one
• CAS: 862549-37-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: OBIWUMHFPMQLMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one 在 三氯化硼 、 sodium hydride 、 甲基磺酰氯 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.92h， 生成 5,5-Bis-hydroxymethyl-3-[3-isobutyl-5-methyl-hex-(E)-ylidene]-dihydro-furan-2-one
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the sn-1 and sn-2 Carbonyl Functionality Reveals the Essential Role of the sn-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C

  摘要：

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.

  DOI：

  10.1021/jm050352m
• 作为产物：
  描述：

  1-(benzyloxy)-2-[(4-methoxyphenoxy)methyl]-4-penten-2-ol 在 ammonium cerium (IV) nitrate 、 dimethyl sulfide borane 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 5.0h， 生成 5-(hydroxymethyl)-5-[(phenylmethoxy)methyl]-3,4,5-trihydrofuran-2-one
  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

• [EN] GLYCEROL COMPOUNDS AND METHODS OF USE<br/>[FR] COMPOSÉS DE GLYCÉROL ET PROCÉDÉS D'UTILISATION
  申请人：ENZYCHEM LIFESCIENCES CORP

  公开号：WO2022058965A1

  公开（公告）日：2022-03-24

  Provided herein,inter alia, are compounds of fatty acid glycerol derivatives and compositions including the same.

  本文提供了脂肪酸甘油衍生物化合物和包含这些化合物的组合物。
• Polar 3-alkylidene-5-pivaloyloxymethyl-5′-hydroxymethyl-γ-lactones as protein kinase C ligands and antitumor agents
  作者：Ji-Hye Kang、Yerim Kim、Shin-Hye Won、Song-Kyu Park、Chang Woo Lee、Hwan-Mook Kim、Nancy E. Lewin、Nicholas A. Perry、Larry V. Pearce、Daniel J. Lundberg、Robert J. Surawski、Peter M. Blumberg、Jeewoo Lee

  DOI：10.1016/j.bmcl.2009.12.058

  日期：2010.2

  A series of DAG-lactones with polar 3-alkylidene substituents have been investigated as PKC-alpha ligands and antitumor agents. Extensive analysis of structure-activity relationships for the 3-alkylidene chain revealed that polar groups such as ether, hydroxyl, aldehyde, ester, acyloxy, and amido were tolerated with similar binding affinities and reduced lipophilicities compared to the corresponding unsubstituted alkylidene chain. Among the derivatives, compounds 5, 6 and 8 with an ether type of side chain showed high binding affinities in range of K-i = 3-5 nM and excellent antitumor profiles, particularly against the colo205 colon cancer and the K562 leukemia cell lines. (c) 2010 Elsevier Ltd. All rights reserved.
• US5874464A
  申请人：——

  公开号：US5874464A

  公开（公告）日：1999-02-23
• [EN] DIACYLGLYCEROL LACTONE COMPOUND, PREPARATION METHOD THEREFOR, AND IMMUNOSTIMULATOR CONTAINING SAME AS ACTIVE INGREDIENT<br/>[FR] COMPOSÉ DE DIACYLGLYCÉROL LACTONE, SON PROCÉDÉ DE FABRICATION ET IMMUNOSTIMULATEUR LE CONTENANT EN TANT QUE PRINCIPE ACTIF<br/>[KO] 디아실글리세롤락톤 화합물, 그 제조방법 및 이를 유효성분으로 함유하는 면역증진제
  申请人：ENZYCHEM LIFESCIENCES CORP

  公开号：WO2019177314A1

  公开（公告）日：2019-09-19

  호중구 이동을 촉진하여 면역을 증진시키고 감염을 억제하는 신규한 디아실글리세롤락톤 화합물, 그 제조방법 및 이를 유효성분으로 함유하는 면역증진제가 개시된다. 상기 디아실글리세롤락톤 화합물은 명세서의 화학식 1로 표시된다. 상기 화학식 1에서, R1 및 R2는 각각 독립적으로 탄소수 2 내지 30의 지방산기이다.
• Conformationally Constrained Analogues of Diacylglycerol (DAG). 25. Exploration of the <i>sn</i>-1 and <i>sn</i>-2 Carbonyl Functionality Reveals the Essential Role of the <i>sn</i>-1 Carbonyl at the Lipid Interface in the Binding of DAG-Lactones to Protein Kinase C
  作者：Ji-Hye Kang、Megan L. Peach、Yongmei Pu、Nancy E. Lewin、Marc C. Nicklaus、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm050352m

  日期：2005.9.1

  Diacylglycerol (DAG) lactones with altered functionality (C=O -> CH2 or C=O -> C=S) at the sn-1 and sn-2 carbonyl pharmacophores were synthesized and used as probes to dissect the individual role of each carbonyl in the binding to protein kinase C (PKC). The results suggest that the hydrated sn-1 carbonyl is engaged in very strong hydrogen-bonding interactions with the charged lipid headgroups and organized water molecules at the lipid interface. Conversely, the sn-2 carbonyl has a more modest contribution to the binding process as a result of its involvement with the receptor (Cl domain) via conventional hydrogen bonding to the protein. The parent DAG-lactones, E-6 and Z-7, were designed to bind exclusively in the sn-2 binding mode to ensure the correct orientation and disposition of pharmacophores at the binding site.