(+/-)-4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole | 184587-77-7

• 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: (+/-)-4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole
• 英文别名: 4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxoindole；4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-2-oxindole；(+/-)-convolutamydine A；convolutamydine A；convulatamydine A；2H-Indol-2-one, 4,6-dibromo-1,3-dihydro-3-hydroxy-3-(2-oxopropyl)-；4,6-dibromo-3-hydroxy-3-(2-oxopropyl)-1H-indol-2-one
• CAS: 184587-77-7
• 化学式: C₁₁H₉Br₂NO₃
• 分子量: 363.005
• InChiKey: UCZPZZBCCIUPSH-UHFFFAOYSA-N

物化性质

• 熔点：
  198-202 °C
• 沸点：
  504.9±50.0 °C(Predicted)
• 密度：
  1.910±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 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：

  (+/-)-4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到3-(2-hydroxypropyl)-4,6-dibromoindole
  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：

  1-acetyl-4,6-dibromoindole 在 4 A molecular sieve 2,6-二甲基吡啶 、 MoO5*HMPA 、 D(+)-10-樟脑磺酸 、 三(二甲氨基)锍二氟三甲基硅酸 、 溴 、 氧气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 、 palladium dichloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 168226.0h， 生成 (+/-)-4,6-dibromo-3-(2-oxopropyl)-3-hydroxy-2-oxindole
  参考文献：
  名称：

  Synthesis of 3-hydroxyindolin-2-one alkaloids, (±)-donaxaridine and (±)-convolutamydines A and E, through enolization–Claisen rearrangement of 2-allyloxyindolin-3-ones

  摘要：

  Claisen rearrangement triggered by enolization of 2-allyloxyindolin-3-ones with DBU was performed in order to prepare 3-allyl-3-hydroxyindolin-2-ones. Total synthesis of 3-hydroxyindolin-2-one alkaloids, (+/-)-donaxaridine, as well as (+/-)-convolutamydines A and E , was achieved by transformation of the allyl moiety of 3-allyl-3-hydroxyindolin-2-ones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.031

文献信息

• Catalyst-free aldol condensation of ketones and isatins under mild reaction conditions in DMF with molecular sieves 4 Å as additive
  作者：Wen-Bing Chen、Yu-Hua Liao、Xi-Lin Du、Xiao-Mei Zhang、Wei-Cheng Yuan

  DOI：10.1039/b906684e

  日期：——

  In the presence of molecular sieve (MS) 4 Å in DMF, a catalyst-free aldol condensation of a variety of aromatic and aliphatic ketones with isatins under mild reaction conditions has been developed. This approach may provide access to a wide range of 3-substituted-3-hydroxyindolin-2-ones in good to excellent yields.

  在DMF中存在4 Å分子筛（MS）的情况下，已经开发出一种无需催化剂的醛酮缩合反应，可以在温和条件下使多种芳香和脂肪酮与靛红反应。这种方法可能提供了一条途径，以良好至优异的产率合成广泛的3-取代-3-羟基吲哚-2-酮。
• A modified Sandmeyer methodology and the synthesis of (±)-convolutamydine A
  作者：Simon J. Garden、JoséC. Torres、Alexandre A. Ferreira、Rosangela B. Silva、Angelo C. Pinto

  DOI：10.1016/s0040-4039(97)00140-8

  日期：1997.3

  (±)-Convolutamydine A (5) has been prepared by a concise synthesis form 3,5-dibromoaniline using a modified Sandmeyer methodology. The modified Sandmeyer methodology has also been found to be beneficial for the synthesis of other α-isonitrosoacetanilides. The 4,6-dibromohydrocyoxindole nucleus was further confirmed by comparison with the isomeric 5,7-dibromohydroxyoxindole.

  （±）-Convolutamydine A（5）已使用改良的Sandmeyer方法通过简明的合成形式3,5-二溴苯胺制备。还发现改进的Sandmeyer方法学对合成其他α-异亚硝基乙酰苯胺有利。通过与异构体5，7-二溴羟基羟吲哚比较，进一步确认了4，6-二溴氢羟吲哚核。
• Synthesis of Convolutamydine A from Isatin
  作者：G. K. Jnaneshwar、V. H. Deshpande

  DOI：10.1039/a904205i

  日期：——

  Synthesis of the marine alkaloid convolutamydine A is described starting from commercially available isatin.

  介绍了海洋生物碱 convolutamydine A 的合成过程，其起始原料是市售的异靛红。
• Microwave Assisted Preparation of Isatins and Synthesis of (±)-Convolutamydine-A
  作者：G. K. Jnaneshwara、A. V. Bedekar、V. H. Deshpande

  DOI：10.1080/00397919908085998

  日期：1999.10

  Microwave assisted preparation of a number of isatin derivatives is reported. A simple synthesis of (+/-)-convolutamydine-A a potent compound against leukemia cells, is presented.
• Anti-inflammatory properties of convolutamydine A and two structural analogues
  作者：Patricia D. Fernandes、Renata S. Zardo、Gabriella S.M. Figueiredo、Bárbara V. Silva、Angelo C. Pinto

  DOI：10.1016/j.lfs.2014.08.019

  日期：2014.10

  Aims: Convolutamydine A is an oxindole alkaloid that can be isolated from a marine bryozoan. Due to the variety of biological effects, two analogues were synthesized and their anti-inflammatory properties were evaluated.Main methods: The anti-inflammatory effects of convolutamydine A and its analogues (ISA003 and ISA147) were investigated in a formalin-induced licking behaviour model, where mice received an intraplantar injection of formalin and their licking behaviour was evaluated for 30 min. Additionally, inflammatory parameters were evaluated in a subcutaneous air pouch (SAP) model of carrageenan-induced inflammation. Exudates were collected for leukocyte counts; measurement of protein, prostaglandin E2 (PGE2) and cytokines by ELISA; and analysis of nitric oxide (NO) using a nitrate conversion protocol. Cyclooxygenase-2 (COX2) and inducible nitric oxide synthase (iNOS) from RAW 264.7 cells were quantified by immunoblotting.Key findings: Convolutamydine A and its two analogues inhibited the formalin-induced licking response at doses as low as 0.01 mg/kg. An inhibitory effect was also observed on leukocyte migration and the production of NO, PGE2 and cytokines (IL-6 and TNF-alpha). The reduction in inflammatory parameters did not appear to be correlated with a direct reduction in the number of cells in the SAP, because a reduction in NO and PGE2 production by cultured macrophages was observed in addition to the inhibition of iNOS and COX2 enzyme expression.Significance: These results indicate that convolutamydine A and its two analogues have significant anti-inflammatory effects. These substances can be improved to generate lead compounds for the synthesis of new anti-inflammatory drugs. (C) 2014 Elsevier Inc. All rights reserved.

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