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3-(4-benzyloxyphenyl)-1-cyclohexylpropan-1-one | 207736-70-7

中文名称
——
中文别名
——
英文名称
3-(4-benzyloxyphenyl)-1-cyclohexylpropan-1-one
英文别名
3-(4-Benzyloxy-phenyl)-1-cyclohexyl-propan-1-one;1-cyclohexyl-3-(4-phenylmethoxyphenyl)propan-1-one
3-(4-benzyloxyphenyl)-1-cyclohexylpropan-1-one化学式
CAS
207736-70-7
化学式
C22H26O2
mdl
——
分子量
322.447
InChiKey
FLZGYJSCXGYVQS-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

物化性质

  • 沸点:
    468.510±25.00 °C(Press: 760.00 Torr)(predicted)
  • 密度:
    1.076±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    5.4
  • 重原子数:
    24
  • 可旋转键数:
    7
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.41
  • 拓扑面积:
    26.3
  • 氢给体数:
    0
  • 氢受体数:
    2

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:
    3-(4-benzyloxyphenyl)-1-cyclohexylpropan-1-onesodium hydroxide正丁基锂 、 sodium hydride 作用下, 以 四氢呋喃正己烷 为溶剂, 反应 6.0h, 生成 6-cyclohexyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydropyran-2-one
    参考文献:
    名称:
    Nonpeptidic HIV protease inhibitors possessing excellent antiviral activities and therapeutic indices. PD 178390: a lead HIV protease inhibitor
    摘要:
    With the insight generated by the availability of X-ray crystal structures of various 5,6-dihydropyran-2-ones bound to HIV PR, inhibitors possessing various alkyl groups at the 6-position of 5,6-dihydropyran-2-one ring were synthesized. The inhibitors possessing a 6-alkyl group exhibited superior antiviral activities when compared to 6-phenyl analogues. Antiviral efficacies were further improved upon introduction of a polar group (hydroxyl or amino) on the 4-position of the phenethyl moiety as well as the polar group (hydroxymethyl) on the 3-(tert-butyl-5-methyl-phenylthio) moiety. The polar substitution is also advantageous for decreasing toxicity, providing inhibitors with higher therapeutic indices. The best inhibitor among this series, (S)-6-[2-(4-aminophenyl)-ethyl]-(3-(2-tert-butyl-5-methyl-phenylsulfa nyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (34S), exhibited an EC50 of 200 nM with a therapeutic index of > 1000. More importantly, these non-peptidic inhibitors, 16S and 34S, appear to offer little cross-resistance to the currently marketed peptidomimetic PR inhibitors. The selected inhibitors tested in vitro against mutant HIV PR showed a very small increase in binding affinities relative to wild-type HIV PR. Cmax and absolute bioavailability of 34S were higher and half-life and time above EC95 were longer compared to 16S. Thus 34S, also known as PD 178390, which displays good antiviral efficacy, promising pharmacokinetic characteristics and favorable activity against mutant enzymes and CYP3A4, has been chosen for further preclinical evaluation.
    DOI:
    10.1016/s0968-0896(99)00215-1
  • 作为产物:
    描述:
    乙酰基环己烷 在 Pd-BaSO4 barium dihydroxide氢气 作用下, 以 四氢呋喃乙醇 为溶剂, 20.0 ℃ 、330.95 kPa 条件下, 反应 8.0h, 生成 3-(4-benzyloxyphenyl)-1-cyclohexylpropan-1-one
    参考文献:
    名称:
    Nonpeptidic HIV protease inhibitors possessing excellent antiviral activities and therapeutic indices. PD 178390: a lead HIV protease inhibitor
    摘要:
    With the insight generated by the availability of X-ray crystal structures of various 5,6-dihydropyran-2-ones bound to HIV PR, inhibitors possessing various alkyl groups at the 6-position of 5,6-dihydropyran-2-one ring were synthesized. The inhibitors possessing a 6-alkyl group exhibited superior antiviral activities when compared to 6-phenyl analogues. Antiviral efficacies were further improved upon introduction of a polar group (hydroxyl or amino) on the 4-position of the phenethyl moiety as well as the polar group (hydroxymethyl) on the 3-(tert-butyl-5-methyl-phenylthio) moiety. The polar substitution is also advantageous for decreasing toxicity, providing inhibitors with higher therapeutic indices. The best inhibitor among this series, (S)-6-[2-(4-aminophenyl)-ethyl]-(3-(2-tert-butyl-5-methyl-phenylsulfa nyl)-4-hydroxy-6-isopropyl-5,6-dihydro-pyran-2-one (34S), exhibited an EC50 of 200 nM with a therapeutic index of > 1000. More importantly, these non-peptidic inhibitors, 16S and 34S, appear to offer little cross-resistance to the currently marketed peptidomimetic PR inhibitors. The selected inhibitors tested in vitro against mutant HIV PR showed a very small increase in binding affinities relative to wild-type HIV PR. Cmax and absolute bioavailability of 34S were higher and half-life and time above EC95 were longer compared to 16S. Thus 34S, also known as PD 178390, which displays good antiviral efficacy, promising pharmacokinetic characteristics and favorable activity against mutant enzymes and CYP3A4, has been chosen for further preclinical evaluation.
    DOI:
    10.1016/s0968-0896(99)00215-1
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文献信息

  • Dihydropyrones with improved antiviral activity
    申请人:Warner-Lambert Company
    公开号:US06046355A1
    公开(公告)日:2000-04-04
    This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions. The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.
    本发明涉及通过在3和/或6位恰当地放置某些极性取代基,改善6,6-二取代-5,6-二氢吡喃-2-酮的抗病毒活性。这些增强细胞活性的相同取代基还降低了细胞毒性,进一步增强了这些化合物作为抗病毒药物的理想性能。
  • DIHYDROPYRONES WITH IMPROVED ANTIVIRAL ACTIVITY
    申请人:WARNER-LAMBERT COMPANY
    公开号:EP0935597A2
    公开(公告)日:1999-08-18
  • US5834506A
    申请人:——
    公开号:US5834506A
    公开(公告)日:1998-11-10
  • US6046355A
    申请人:——
    公开号:US6046355A
    公开(公告)日:2000-04-04
  • [EN] DIHYDROPYRONES WITH IMPROVED ANTIVIRAL ACTIVITY<br/>[FR] DIHYDROPYRONES A ACTIVITE ANTIVIRALE AMELIOREE
    申请人:——
    公开号:WO1998019997A2
    公开(公告)日:1998-05-14
    [EN] This invention pertains to improved antiviral activity of 6,6-disubstituted-5,6-dihydropyran-2-ones caused by judicious placement of certain polar substituents at the 3 and/or 6 positions. The same substituents which enhance the cellular activity also diminish cytotoxicity further enhancing the desirable properties of these agents as antivirals.
    [FR] La présente invention concerne une amélioration de l'activité antivirale de 5,6-dihydropyran-2-ones disubstitués en 6,6 obtenue grâce à une disposition judicieuse de substituants en positions 3 et/ou 6. Ces mêmes substituants qui renforcent l'activité cellulaire diminuent également la cytotoxicité, ce qui renforce encore plus les propriétés souhaitables de ces agents comme antiviraux.
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