3-hydroxy-3-trimethylsilylmethyloxindole

• 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: 3-hydroxy-3-trimethylsilylmethyloxindole
• 英文别名: 3-hydroxy-3-(trimethylsilylmethyl)-1H-indol-2-one
• 化学式: C₁₂H₁₇NO₂Si
• 分子量: 235.358
• InChiKey: KQNPCFLCGYEYAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-3-trimethylsilylmethyloxindole 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 3-亚甲基氧化吲哚
  参考文献：
  名称：

  从 3-Ylideneoxindoles 合成功能化的 Spiroaziridine-oxindoles：生成 3-（氨基烷基）oxindoles 的简单途径

  摘要：

  通过在 CaO 存在下用 N-{[(4-硝基苯基)磺酰基]氧基}氨基甲酸酯 (NsONHCO2Et) 处理容易获得的 3-ylideneoxindoles，制备了新型的具有潜在生物活性的螺氮丙啶-oxindoles。这些化合物通过简单且区域选择性的还原性氮丙啶开环反应生成了新的 3-（氨基烷基）羟吲哚衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）

  DOI：

  10.1002/ejoc.200900891
• 作为产物：
  描述：

  (三甲基硅基)甲基氯化镁 、 靛红 以 四氢呋喃 、 乙醚 为溶剂， 生成 3-hydroxy-3-trimethylsilylmethyloxindole
  参考文献：
  名称：

  从 3-Ylideneoxindoles 合成功能化的 Spiroaziridine-oxindoles：生成 3-（氨基烷基）oxindoles 的简单途径

  摘要：

  通过在 CaO 存在下用 N-{[(4-硝基苯基)磺酰基]氧基}氨基甲酸酯 (NsONHCO2Et) 处理容易获得的 3-ylideneoxindoles，制备了新型的具有潜在生物活性的螺氮丙啶-oxindoles。这些化合物通过简单且区域选择性的还原性氮丙啶开环反应生成了新的 3-（氨基烷基）羟吲哚衍生物。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2009）

  DOI：

  10.1002/ejoc.200900891

文献信息

• A convenient synthesis of 3-methyleneoxindoles: cytotoxic metabolites of indole-3-acetic acids
  作者：Sharon Rossiter

  DOI：10.1016/s0040-4039(02)00855-9

  日期：2002.5

  3-Methyleneoxindole is a cytotoxic metabolite of indole-3-acetic acid with potential for use in cancer therapy. This species and ring-substituted analogues are conveniently synthesised from the corresponding isatins via a Peterson olefination.

  3-亚甲基羟吲哚是吲哚-3-乙酸的细胞毒性代谢产物，有可能用于癌症治疗。该物质和环取代的类似物可方便地通过彼得森烯化反应从相应的靛红合成。
• Modular Assembly of Six‐Membered Carbocyclic Spirooxindoles via Peterson Olefination/Michael Addition/C(sp3) Arylation Cascade
  作者：Feng‐Cheng Jia、Zi‐Yi Yuan、Na Luo、Shuang‐Xi Gu、Xiao‐Qiang Hu

  DOI：10.1002/cjoc.202400410

  日期：2024.11

  tolerance (> 50 examples). Mechanistic experiments revealed that this reaction involved a Peterson olefination, Michael addition and intramolecular C(sp3) arylation cascade. The variegated synthetic derivatization of target products and successful construction of bioactive molecules further illustrate the synthetic potential in spirooxindole-related drug discovery.

  螺氧吲哚的简洁组装具有重要意义，但在现代有机合成中是一项具有挑战性的任务。本文描述的是很少使用的盐丁衍生的 β-甲硅烷基甲醇与 o-卤素芳香酮的不寻常的碱促进 [4+2] 螺缩氢，它能够快速和模块化地合成六元碳环螺吲哚，产量高，具有优异的官能团耐受性（> 50个例子）。机理实验表明，该反应涉及 Peterson 烯化、Michael 加成和分子内 C（sp3） 芳基化级联反应。靶产品的杂色合成衍生化和生物活性分子的成功构建进一步说明了螺吲哚相关药物发现的合成潜力。
• Alantrypinone and its derivatives: Synthesis and antagonist activity toward insect GABA receptors
  作者：Takayuki Watanabe、Mitsuhiro Arisawa、Kenji Narusuye、Mohommad Sayed Alam、Kazumi Yamamoto、Masaaki Mitomi、Yoshihisa Ozoe、Atsushi Nishida

  DOI：10.1016/j.bmc.2008.11.017

  日期：2009.1

  The gamma-aminobutyric acid (GABA) receptor bears important sites of action for insecticides. Alantrypinone is an insecticidal alkaloid that acts as a selective antagonist for housefly (vs rat) GABA receptors, and is considered to be a lead compound for the development of a safer insecticide. In an attempt to obtain compounds with greater activity, a series of racemic alantrypinone derivatives were systematically synthesized using hetero Diels-Alder reactions, and a total of34 compounds were examined for their ability to inhibit the specific binding of [H-3]4'-ethynyl-4-n-propylbicycloorthobenzoate, a high-affinity non-competitive antagonist, to housefly-head membranes. The assay results showed that (1) there is no significant difference between the potencies of natural (+)-alantrypinone and its synthetic racemate; (2) the amide NHs at the 2- and 18-positions are important for high activity; (3) there is a considerable drop in potency for compounds without an aromatic ring at the 16-position; and (4) a large substituent at the 3-position is detrimental to high activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Natural α-methylenelactam analogues: Design, synthesis and evaluation of α-alkenyl-γ and δ-lactams as potential antifungal agents against Colletotrichum orbiculare
  作者：Wang Delong、Wang Lanying、Wu Yongling、Song Shuang、Feng Juntao、Zhang Xing

  DOI：10.1016/j.ejmech.2017.02.050

  日期：2017.4

  In our continued efforts to improve the potential utility of the alpha-methylene-gamma-lactone scaffold, 62 new and 59 known natural alpha-methylenelactam analogues including alpha-methylene-gamma- lactams, alpha-arylidene- gamma and delta-lactams, and 3-arylideneindolin-2-ones were synthesized as the bioisosteric analogues of the amethylenelactone scaffold. The results of antifungal and cytotoxic activity indicated that among these derivatives compound (E)-1-(2, 6-dichlorobenzyl)-3-(2-fluorobenzylidene) pyrrolidin-2-one (Py51) possessed good selectivity with the highest antifungal activity against Colletotrichum orbiculare with IC50 - 10.4 mu M but less cytotoxic activity with IC50 - 141.2 mu M (against HepG2 cell line) and 161.2 mu M ( against human hepatic L02 cell line). Ultrastructural change studies performed by transmission electron microscope showed that Py51 could cause important cell morphological changes in C. orbiculare, such as plasma membrane detached from cell wall, cell wall thickening, mitochondria disruption, a dramatic increase in vacuolation, and eventually a complete loss in the integrity of organelles. Significantly, mitochondria appeared one of the primary targets, as confirmed by their remarkably aberrant morphological changes. Analysis of structureeactivity relationships revealed that incorporation of the aryl group into the alpha-exo methylene and the N-benzyl substitution increased the activity. Meanwhile, the alpha-arylidene-gamma-lactams have superiority in selectivity over the 3-arylideneindolin-2-ones. Based on the results, the N- benzyl substituted a-(2-fluorophenyl)-gamma-lactam was identified as the most promising natural- based scaffold for further discovering and developing improved crop- protection agents. (c) 2017 Elsevier Masson SAS. All rights reserved.