1-(4-甲氧基苯氧基)-3-苯基甲氧基丙烷-2-酮 | 213828-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-甲氧基苯氧基)-3-苯基甲氧基丙烷-2-酮
• 英文名称: 1-(benzyloxy)-3-(4-methoxyphenoxy)acetone
• 英文别名: 2-Propanone, 1-(4-methoxyphenoxy)-3-(phenylmethoxy)-；1-(4-methoxyphenoxy)-3-phenylmethoxypropan-2-one
• CAS: 213828-28-5
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: NNVNFKSIRROKIB-UHFFFAOYSA-N

物化性质

• 熔点：
  58.8 °C
• 沸点：
  442.6±30.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苯氧基)-3-苯基甲氧基丙烷-2-酮 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 7.0h， 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
• 作为产物：
  描述：

  2,3-环氧丙基-4-甲氧基苯基醚 在 pyridinium chloroformate 、 4 A molecular sieve 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 1-(4-甲氧基苯氧基)-3-苯基甲氧基丙烷-2-酮
  参考文献：
  名称：

  基于四氢呋喃模板的蛋白激酶C配体，其中包含一组新的佛波酯酯药效基团。

  摘要：

  根据立体化学，一系列带有嵌入的甘油骨架的取代的四氢呋喃系列带有附加的四氢呋喃亚基乙酸盐或四氢呋喃基乙酸盐基序，分为四个不同的模板（I-IV）。根据新的修订模型，将这些化合物设计为模仿佛波酯的三个基本药效基团（C（3）-C = O，C（20）-OH和C（13）-C = O）。由缩水甘油基4-甲氧基苯基醚构成四氢呋喃环，并通过NMR光谱法（包括NOE）确定异构体模板的结构。对蛋白激酶C（PKC）的结合亲和力是根据配体从PKC的重组α同工酶置换结合的[（3）H-20] phorbol 12、13-二丁酸酯（PDBU）的能力来评估的。Z和E几何异构体（1、3，分别含有四氢呋喃亚基乙酸盐基序的）是最有效的配体，它们的K（i）值相同，为0.35 microM。对这四个模板的分子建模研究表明，当拟合到典型的佛波醇12,13-二乙酸酯时，均方根值与亲和力成反比，其相关性依次为：I约II> III> IV。

  DOI：

  10.1021/jm980713g

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。
• Conformationally Constrained Analogues of Diacylglycerol (DAG). 28. DAG-dioxolanones Reveal a New Additional Interaction Site in the C1b Domain of PKCδ
  作者：Yongseok Choi、Yongmei Pu、Megan L. Peach、Ji-Hye Kang、Nancy E. Lewin、Dina M. Sigano、Susan H. Garfield、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm0702579

  日期：2007.7.1

  Diacylglycerol (DAG) lactones have provided a powerful platform for structural exploration of the interactions between ligands and the C1 domains of protein kinase C (PKC). In this study, we report that DAG-dioxolanones, novel derivatives of DAG-lactones, exploit an additional point of contact (glutamine 27) in their binding with the C1b domain of PKC delta. Mutation of this point of contact to glutamate selectively impairs binding of the DAG-dioxolanones compared to that of the corresponding DAG-lactones (1200- to 3000-fold versus 35- to 55-fold, respectively). The differential response of this mutated C1b domain to the DAG-dioxolanones relative to the DAG-lactones provides a unique tool to probe the role of the C1b domain in PKC delta function, where the response to the DAG-lactones affords a positive control for retained function. Using this approach, we show that the C1b domain of PKC delta plays the predominant role in the translocation of PKC delta to the membrane in the presence of DAG.
• Conformationally Constrained Analogues of Diacylglycerol (DAG). 23. Hydrophobic Ligand−Protein Interactions versus Ligand−Lipid Interactions of DAG-Lactones with Protein Kinase C (PK-C)
  作者：Hirokazu Tamamura、Dina M. Sigano、Nancy E. Lewin、Megan L. Peach、Marc C. Nicklaus、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm049723+

  日期：2004.9.1

  The constrained glycerol backbone of DAG-lactones, when combined with highly branched alkyl chains, has engendered a series of DAG-lactone ligands capable of binding protein kinase C (PK-C) with affinities that approximate those of phorbol esters. These branched chains not only appear to be involved in making important hydrophobic contacts with the protein (specific interactions) but also provide adequate lipophilicity to facilitate partitioning into the lipid-rich membrane environment (nonspecific interactions). With the idea of minimizing the nonspecific interactions without reducing lipophilicity, the present work explores the strategy of relocating lipophilicity from the side chain to the lactone "core". Such a transfer of lipophilicity, exemplified by compounds I and 3, was conceived to allow the new hydrophobic groups on the lactone to engage in specific hydrophobic contacts inside the binding pocket without any expectation of interfering with the hydrogen-bonding network of the DAG-lactone pharmacophore. Surprisingly, both (E)-3 and (Z)-3 showed a significant decrease in binding affinity. From the molecular docking studies performed with the new ligands, we conclude that the binding pocket of the C I domain of PK-C is sterically restricted and prevents the methyl groups at the C-3 position of the lactone from engaging in productive hydrophobic contacts with the receptor.
• [EN] DIACYGLYCEROL MIMETICS AND METHODS OF USING THE SAME AS PROTEIN KINASE C ALPHA ACTIVATORS AND APOPTOSIS INDUCERS<br/>[FR] MIMETIQUES DE DIACYLGLYCEROL ET LEURS PROCEDES D'UTILISATION EN TANT QU'ACTIVATEURS DE LA PROTEINE KINASE C ALPHA ET EN TANT QU'INDUCTEURS D'APOPTOSE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2003013504A1

  公开（公告）日：2003-02-20

  Disclosed herein are methods for inducing apoptosis by exposing cells to an apoptic inducing amount of one or more of newly created DAG-lactone mimetics. In one embodiment of the new class of DAG compounds the new DAG-mimetic compound satisfies general formula (I) as follows:, wherein R1, R2, R3, and R4 are independently selected from the group consisting essentially of hydrogen, oxygen, nitrogen, hydroxyls, halogens, branched or unbranched, substituted or unsubstituted, aliphatic groups, heteroatom (e.g., O, S, N, hydroxyls, halogens) substituted aliphatic groups, aromatic groups, and all major functional groups. Preferably, R1 is O and R3 is a hydroxyalkyl such as CH2OH. Also preferably, R2 is an alkylidene group derived from an aldehyde and R4 is an alkyl group derived from an acid chloride. The size of the lactone ring may be varied by either increasing or decreasing the ring size. Preferably, R1, R2, R3, and R4 when comprising carbon chains or rings, comprise groups of carbon chains or rings of 12 carbon atoms or less.
• [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.