(2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one | 52121-55-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one
• 英文别名: (E)-1-cyclopropyl-3-(4-phenylmethoxyphenyl)prop-2-en-1-one
• CAS: 52121-55-8
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: JYDGDGYMSUEFMF-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one 在 palladium on activated charcoal 、 Pd-BaSO₄ 正丁基锂 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 6-cyclopropyl-4-hydroxy-6-[2-(4-hydroxyphenyl)ethyl]-5,6-dihydro-pyran-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：

  4-苄氧基苯甲醛 、 环丙甲基酮 在 sodium hydroxide 水 、 乙醇 作用下， 以 乙醇 、 水 为溶剂， 反应 16.33h， 以to give (2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one (6.29 g)的产率得到(2E)-3-[4-(benzyloxy)phenyl]-1-cyclopropyl-2-propen-1-one
  参考文献：
  名称：

  Pyrazole derivatives

  摘要：

  化合物的公式(I)：其中R1是氢或较低的烷基；R2是较低的烷基等；R3是较低的烷氧基等；R4是羟基等；X是O，S等；Y是CH或N；Z是较低的烷基或较低的烯基；m为0或1；或其盐。这些化合物可用作药物。

  公开号：

  US20040116475A1

文献信息

• Pyrazole Derivatives
  申请人：SHIRAI Fumiyuki

  公开号：US20070112037A1

  公开（公告）日：2007-05-17

  A compound of the formula (I): wherein R 1 is hydrogen or lower alkyl; R 2 is lower alkyl, etc.; R 3 is lower alkoxy, etc.; R 4 is hydroxy, etc.; X is O, S, etc.; Y is CH or N; Z is lower alkylene or lower alkenylene; and m is 0 or 1; or salts thereof, which are useful as a medicament.

  化合物的公式（I）：其中R1为氢或低级烷基；R2为低级烷基等；R3为低级烷氧基等；R4为羟基等；X为O，S等；Y为CH或N；Z为低级烷基或低级烯基；m为0或1；或其盐。这些化合物在药物方面有用。
• PYRAZOLE DERIVATIVES USEFUL AS COX-I INHIBITORS
  申请人：Astellas Pharma Inc.

  公开号：EP1567503B1

  公开（公告）日：2011-12-21
• US4182729A
  申请人：——

  公开号：US4182729A

  公开（公告）日：1980-01-08
• US4166074A
  申请人：——

  公开号：US4166074A

  公开（公告）日：1979-08-28
• US4171378A
  申请人：——

  公开号：US4171378A

  公开（公告）日：1979-10-16