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phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate | 1452161-96-4

中文名称
——
中文别名
——
英文名称
phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate
英文别名
Phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate
phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate化学式
CAS
1452161-96-4
化学式
C13H14O5
mdl
——
分子量
250.251
InChiKey
HDFKQIPNKAJRCW-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.3
  • 重原子数:
    18
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.38
  • 拓扑面积:
    61.8
  • 氢给体数:
    0
  • 氢受体数:
    5

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    甲瓦龙酸内酯吡啶4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 四丁基溴化铵氢气盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 potassium hydroxide 作用下, 以 四氢呋喃二氯甲烷乙酸乙酯乙腈 为溶剂, 反应 7.25h, 生成 phenyl 2-(4-methyl-2-oxo-1,3-dioxan-4-yl)acetate
    参考文献:
    名称:
    Synthesis of mevalonate- and fluorinated mevalonate prodrugs and their in vitro human plasma stability
    摘要:
    The mevalonate pathway is essential for the production of many important molecules in lipid biosynthesis. Inhibition of this pathway is the mechanism of statin cholesterol-lowering drugs, as well as the target of drugs to treat osteoporosis, to combat parasites, and to inhibit tumor cell growth. Unlike the human mevalonate pathway, the bacterial pathway appears to be regulated by diphosphomevalonate (DPM). Enzymes in the mevalonate pathway act to produce isopentenyl diphosphate, the product of the DPM decarboxylase reaction, utilize phosphorylated (charged) intermediates, which are poorly bioavailable. It has been shown that fluorinated DPMs (6-fluoro- and 6,6,6-trifluoro-5diphosphomevalonate) are excellent inhibitors of the bacterial pathway; however, highly charged DPM and analogs are not bioavailable. To increase cellular permeability of mevalonate analogs, we have synthesized various prodrugs of mevalonate and 6-fluoro- and 6,6,6-trifluoromevalonate that can be enzymatically transformed to the corresponding DPM or fluorinated DPM analogs by esterases or amidases. To probe the required stabilities as potentially bioavailable prodrugs, we measured the half-lives of esters, amides, carbonates, acetals, and ketal promoieties of mevalonate and the fluorinated mevalonate analogs in human blood plasma. Stability studies showed that the prodrugs are converted to the mevalonates in human plasma with a wide range of half-lives. These studies provide stability data for a variety of prodrug options having varying stabilities and should be very useful in the design of appropriate prodrugs of mevalonate and fluorinated mevalonates. (C) 2014 Elsevier Masson SAS. All rights reserved.
    DOI:
    10.1016/j.ejmech.2014.11.040
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文献信息

  • [EN] PRODRUGS OF FLUORINATED MEVALONATES TO INHIBIT THE MEVALONATE PATHWAY OF STREPTOCOCCUS PNEUMONIAE<br/>[FR] PROMÉDICAMENTS DE MÉVALONATES FLUORÉS POUR INHIBER LA VOIE DU MÉVALONATE DU PNEUMOCOQUE
    申请人:UNIV NORTHWESTERN
    公开号:WO2013130792A3
    公开(公告)日:2013-10-24
  • Prodrugs of Fluorinated Mevalonates to Inhibit the Mevalonate Pathway of Streptococcus pneumoniae
    申请人:Silverman Richard B.
    公开号:US20130245284A1
    公开(公告)日:2013-09-19
    Fluorinated prodrug compounds as can be used for selective streptococcal mevalonate pathway inhibition.
  • US9150534B2
    申请人:——
    公开号:US9150534B2
    公开(公告)日:2015-10-06
  • Synthesis of mevalonate- and fluorinated mevalonate prodrugs and their in vitro human plasma stability
    作者:Soosung Kang、Mizuki Watanabe、J.C. Jacobs、Masaya Yamaguchi、Samira Dahesh、Victor Nizet、Thomas S. Leyh、Richard B. Silverman
    DOI:10.1016/j.ejmech.2014.11.040
    日期:2015.1
    The mevalonate pathway is essential for the production of many important molecules in lipid biosynthesis. Inhibition of this pathway is the mechanism of statin cholesterol-lowering drugs, as well as the target of drugs to treat osteoporosis, to combat parasites, and to inhibit tumor cell growth. Unlike the human mevalonate pathway, the bacterial pathway appears to be regulated by diphosphomevalonate (DPM). Enzymes in the mevalonate pathway act to produce isopentenyl diphosphate, the product of the DPM decarboxylase reaction, utilize phosphorylated (charged) intermediates, which are poorly bioavailable. It has been shown that fluorinated DPMs (6-fluoro- and 6,6,6-trifluoro-5diphosphomevalonate) are excellent inhibitors of the bacterial pathway; however, highly charged DPM and analogs are not bioavailable. To increase cellular permeability of mevalonate analogs, we have synthesized various prodrugs of mevalonate and 6-fluoro- and 6,6,6-trifluoromevalonate that can be enzymatically transformed to the corresponding DPM or fluorinated DPM analogs by esterases or amidases. To probe the required stabilities as potentially bioavailable prodrugs, we measured the half-lives of esters, amides, carbonates, acetals, and ketal promoieties of mevalonate and the fluorinated mevalonate analogs in human blood plasma. Stability studies showed that the prodrugs are converted to the mevalonates in human plasma with a wide range of half-lives. These studies provide stability data for a variety of prodrug options having varying stabilities and should be very useful in the design of appropriate prodrugs of mevalonate and fluorinated mevalonates. (C) 2014 Elsevier Masson SAS. All rights reserved.
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