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(3R,3aR,6R,6aR)-3,6-bis[(3-fluorophenyl)methoxy]-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione | 214139-76-1

中文名称
——
中文别名
——
英文名称
(3R,3aR,6R,6aR)-3,6-bis[(3-fluorophenyl)methoxy]-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione
英文别名
——
(3R,3aR,6R,6aR)-3,6-bis[(3-fluorophenyl)methoxy]-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione化学式
CAS
214139-76-1
化学式
C20H16F2O6
mdl
——
分子量
390.34
InChiKey
DNGIPSYFJXYDPD-BRSBDYLESA-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):
    2.7
  • 重原子数:
    28
  • 可旋转键数:
    6
  • 环数:
    4.0
  • sp3杂化的碳原子比例:
    0.3
  • 拓扑面积:
    71.1
  • 氢给体数:
    0
  • 氢受体数:
    8

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

  • 作为反应物:
    描述:
    (1S,2R)-(-)-1-氨基-2-茚醇(3R,3aR,6R,6aR)-3,6-bis[(3-fluorophenyl)methoxy]-3,3a,6,6a-tetrahydrofuro[3,2-b]furan-2,5-dione2-羟基吡啶 作用下, 以 1,2-二氯乙烷 为溶剂, 以67%的产率得到N1,N6-di[(1S,2R)-2-hydroxy-2,3-dihydro-1H-1-indenyl]-(2R,3R,4R,5R)-2,5-di(3-fluorobenzyloxy)-3,4-dihydroxyhexanediamide
    参考文献:
    名称:
    Design and Synthesis of Potent C2-Symmetric Diol-Based HIV-1 Protease Inhibitors:  Effects of Fluoro Substitution
    摘要:
    Implementation of derivatized carbohydrates as C-2-symmetric HIV-1 protease inhibitors has previously been reported. With the objective of improving the anti-HIV activity of such compounds, we synthesized a series of fluoro substituted P1/P1 ' analogues. These compounds were evaluated for antiviral activity toward both wild type and mutant virus. The potency of the analogues in blocking HIV-1 protease was moderate, with K-i values ranging from 1 to 7 nM. Nonetheless, compared to the parent nonfluorous inhibitors, a majority of the compounds exhibited improved antiviral activity, for example the 3-fluorobenzyl derivative 9b, which had a K-i value of 7.13 nM and displayed one of the most powerful antiviral activities in the cellular assay of the series. Our results strongly suggest that fluoro substitution can substantially improve antiviral activity. The X-ray crystal structures of two of the fluoro substituted inhibitors (9a and 9f) cocrystallized with HIV-1 protease are discussed.
    DOI:
    10.1021/jm001134q
  • 作为产物:
    参考文献:
    名称:
    Design and Synthesis of Potent C2-Symmetric Diol-Based HIV-1 Protease Inhibitors:  Effects of Fluoro Substitution
    摘要:
    Implementation of derivatized carbohydrates as C-2-symmetric HIV-1 protease inhibitors has previously been reported. With the objective of improving the anti-HIV activity of such compounds, we synthesized a series of fluoro substituted P1/P1 ' analogues. These compounds were evaluated for antiviral activity toward both wild type and mutant virus. The potency of the analogues in blocking HIV-1 protease was moderate, with K-i values ranging from 1 to 7 nM. Nonetheless, compared to the parent nonfluorous inhibitors, a majority of the compounds exhibited improved antiviral activity, for example the 3-fluorobenzyl derivative 9b, which had a K-i value of 7.13 nM and displayed one of the most powerful antiviral activities in the cellular assay of the series. Our results strongly suggest that fluoro substitution can substantially improve antiviral activity. The X-ray crystal structures of two of the fluoro substituted inhibitors (9a and 9f) cocrystallized with HIV-1 protease are discussed.
    DOI:
    10.1021/jm001134q
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文献信息

  • Design and Synthesis of Potent <i>C</i><sub>2</sub>-Symmetric Diol-Based HIV-1 Protease Inhibitors:  Effects of Fluoro Substitution
    作者:David Pyring、Jimmy Lindberg、Åsa Rosenquist、Guido Zuccarello、Ingemar Kvarnström、Hong Zhang、Lotta Vrang、Torsten Unge、Bjorn Classon、Anders Hallberg、Bertil Samuelsson
    DOI:10.1021/jm001134q
    日期:2001.9.1
    Implementation of derivatized carbohydrates as C-2-symmetric HIV-1 protease inhibitors has previously been reported. With the objective of improving the anti-HIV activity of such compounds, we synthesized a series of fluoro substituted P1/P1 ' analogues. These compounds were evaluated for antiviral activity toward both wild type and mutant virus. The potency of the analogues in blocking HIV-1 protease was moderate, with K-i values ranging from 1 to 7 nM. Nonetheless, compared to the parent nonfluorous inhibitors, a majority of the compounds exhibited improved antiviral activity, for example the 3-fluorobenzyl derivative 9b, which had a K-i value of 7.13 nM and displayed one of the most powerful antiviral activities in the cellular assay of the series. Our results strongly suggest that fluoro substitution can substantially improve antiviral activity. The X-ray crystal structures of two of the fluoro substituted inhibitors (9a and 9f) cocrystallized with HIV-1 protease are discussed.
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同类化合物

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