(E)-1-(1H-indol-3-yl)-4-methylpent-1-en-3-one | 36802-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-1-(1H-indol-3-yl)-4-methylpent-1-en-3-one
• CAS: 36802-04-7
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: LKWRBFKJCMMGSC-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(1H-indol-3-yl)-4-methylpent-1-en-3-one 在 5percent Pd/BaSO₄ sodium hydroxide 、 氢气 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、220.64 kPa 条件下， 反应 29.33h， 生成 5-[2-tert-butyl-4-(hydroxymethyl)-5-methyl-phenyl]sulfanyl-4-hydroxy-2-[2-(1H-indol-3-yl)ethyl]-2-isopropyl-3H-pyran-6-one
  参考文献：
  名称：

  4-Hydroxy-5,6-dihydropyrones as Inhibitors of HIV Protease:  The Effect of Heterocyclic Substituents at C-6 on Antiviral Potency and Pharmacokinetic Parameters

  摘要：

  Due largely to the emergence of multi-drug-resistant HIV strains, the development of new HIV protease inhibitors remains a high priority for the pharmaceutical industry. Toward this end, we previously identified a 4-hydroxy-5,6-dihydropyrone lead compound (CI-1029, 1) which possesses excellent activity against the protease enzyme, good antiviral efficacy in cellular assays, and promising bioavailability in several animal species. The search for a suitable backup candidate centered on the replacement of the aniline moiety at C-6 with an appropriately substituted heterocyle. In general, this series of heterocyclic inhibitors displayed good activity (in both enzymatic and cellular tests) and-low cellular toxicity; furthermore, several analogues exhibited improved pharmacokinetic parameters in animal models. The compound with the best combination of high potency, low toxicity, and favorable bioavailabilty was (S)-3-(2-tertbutyl-4-hydroxymethy1- 5-methyl-phenylsulfanyl)-4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (13-(S)). This thiophene derivative also exhibited excellent antiviral efficacy against mutant HIV protease and resistant HIV strains. For these reasons, compound 13-(S) was chosen for further preclinical evaluation.

  DOI：

  10.1021/jm0003844
• 作为产物：
  描述：

  3-吲哚甲醛 、 3-methyl-2-oxo-butylphosphonic acid dimethyl ester 在 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 23.0h， 以57%的产率得到(E)-1-(1H-indol-3-yl)-4-methylpent-1-en-3-one
  参考文献：
  名称：

  Enantioselective Conjugate Addition of Alkenylboronic Acids to Indole-Appended Enones

  摘要：

  An enantioselective addition of alkenylboronic acids and alkynylboronic esters to unprotected indole-appended enones is reported. This transformation proceeds with high enantioselectivity and high product yields via the use of catalytic amounts of 3,3'-bis(pentafluorophenyl)-BINOL and Mg(Ot-Bu)(2). A range of a-branched indole derivatives are available from the transformation.

  DOI：

  10.1021/ol2020847