5-iodo-3-hydroxy-3-(2-oxopropyl)-2-oxindole | 76325-68-3

• 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: 5-iodo-3-hydroxy-3-(2-oxopropyl)-2-oxindole
• 英文别名: 5-iodo-3-(2-oxopropyl)-3-hydroxy-2-oxindole；3-Hydroxy-5-iodo-3-(2-oxopropyl)-2,3-dihydro-1H-indol-2-one；3-hydroxy-5-iodo-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 76325-68-3
• 化学式: C₁₁H₁₀INO₃
• 分子量: 331.11
• InChiKey: UNNHYABJRXLWSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-iodo-3-hydroxy-3-(2-oxopropyl)-2-oxindole 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到3-(2-hydroxypropyl)-5-iodoindole
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7
• 作为产物：
  描述：

  5-碘吲哚醌 、 丙酮 在 二乙胺 作用下， 以80%的产率得到5-iodo-3-hydroxy-3-(2-oxopropyl)-2-oxindole
  参考文献：
  名称：

  A versatile synthetic methodology for the synthesis of tryptophols

  摘要：

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01048-7

文献信息

• Synthesis of potential anticonvulsants: Condensation of isatins with acetone and related ketones
  作者：F.D. Popp、R. Parson、B.E. Donigan

  DOI：10.1002/jps.2600691035

  日期：1980.10

  Substituted isatins were condensed with acetone and other ketones to give analogs of 3-hydroxy-3-acetonyloxindole. Some of these alcohols were dehydrated. Several compounds with anticonvulsant activity were obtained.

  将取代的靛红与丙酮和其他酮缩合，得到3-羟基-3-丙酮酰新吲哚的类似物。这些醇中有些是脱水的。获得了几种具有抗惊厥活性的化合物。
• POPP F. D.; PARSON R.; DONIGAN B. E., J. PHARM. SCI., 1980, 69, NO 10, 1235-1237
  作者：POPP F. D.、 PARSON R.、 DONIGAN B. E.

  DOI：——

  日期：——
• A versatile synthetic methodology for the synthesis of tryptophols
  作者：Simon J Garden、Rosângela B da Silva、Angelo C Pinto

  DOI：10.1016/s0040-4020(02)01048-7

  日期：2002.10

  Tryptophols have been obtained in high yields by the reduction of 3-substituted-dioxindoles (obtained by the aldol condensation reaction of ketones with isatins or by a modified Knovenagel malonate condensation) using a borane tetrahydrofuran complex. The reported methodology offers distinct advantages over existing methods for the synthesis of these compounds, including consistently greater yields, diastereoselective syntheses and the possibility for the synthesis of a wide range of structurally different tryptophols. The reduction reaction was found to proceed via an intermediate 1,3-diol-oxindole, which was obtained diastereoselectively and, which was subsequently reduced to the corresponding tryptophol. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Central and peripheral antinociceptive activity of 3-(2-oxopropyl)-3-hydroxy-2-oxindoles
  作者：Thais Biondino Sardella Giorno、Yáskara L.L. Ballard、Millena Santos Cordeiro、Bárbara V. Silva、Angelo C. Pinto、Patricia Dias Fernandes

  DOI：10.1016/j.pbb.2015.05.004

  日期：2015.8

  Convolutamydine A has been shown to develop a significant antinociceptive effect. Here we demonstrated that new analogues (5-iodo-3-(2-oxopropyl)-3-hydroxy-2-oxindole (5-Iisa), 5-fluoro-3-(2-oxopropy1)-3-hydroxy-2-oxindole (5-Fisa), 5-chloro-3-(2-oxopropyl)-3-hydroxy-2-oxindole (5-Clisa) and 5-methyl-3-(2-oxopropyl)3-hydroxy-2-oxindole (5-Meisa)), at 0.1-10 mg/kg doses, have significant peripheral and central antinociceptive effects in thermal and chemical models of nociception. Oral administered analogues demonstrated more pronounced antinociceptive effects than that obtained with the classical opioid drug morphine (5 mg/kg) in the first and second phases of formalin-induced licking. In the tail flick model, 5-Clisa and 5-Meisa antinociceptive effect was almost twice as that observed with the same dose of morphine. The concomitant administration of diverse antagonists and the analogues indicates that 5-Iisa effects involve the activation of opioid pathway. On the other hand, 5-Fisa and 5-Clisa have the participation of opioid, nitrergic, cholinergic adrenergic and serotoninergic pathways and 5-Meisa has the involvement of opioid, serotoninergic and cholinergic pathways. In conclusion, our results suggest that the new four analogues from Convolutamydine A have significant antinociceptive effects in thermal and chemical induced nociception and could be used in development of new drugs to be used in pain treatment with reduced side effects. (C) 2015 Elsevier Inc. All rights reserved.