6-nitro-1-(phenylsulfonyl)-1H-indole | 73282-17-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-nitro-1-(phenylsulfonyl)-1H-indole
• 英文别名: 1-(benzenesulfonyl)-6-nitroindole
• CAS: 73282-17-4
• 化学式: C₁₄H₁₀N₂O₄S
• 分子量: 302.31
• InChiKey: SEEFFVRQZSCTOF-UHFFFAOYSA-N

物化性质

• 熔点：
  197-200 °C
• 沸点：
  530.4±42.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-nitro-1-(phenylsulfonyl)-1H-indole 在 四甲基乙二胺 、 palladium 10% on activated carbon 、 氢气 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 14.67h， 生成 6-(N,N-diethylamino)-2-iodo-1-(phenylsulfonyl)-1H-indole
  参考文献：
  名称：

  MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes

  摘要：

  A small library of six polarity-sensitive fluorescent dyes, nicknamed MediaChrom, was prepared. This class of dyes is characterized by a pyrimidoindolone core fitted out with a conjugated push pull system and a carboxy linker for a conceivable coupling with biomolecules. The optimized eight-step synthetic strategy involves a highly chemo- and regioselective gold-catalyzed cycloisomerization reaction. The photophysical properties of MediaChrom dyes have been evaluated in-depth. In particular, the MediaChrom bearing a diethylamino as an electron-donating group and a trifluormethyl as an electron-withdrawing group displays the most interesting and advantageous spectroscopic features (e.g., absorption and emission in the visible range and a good quantum yield). Promising results in terms of sensitivity have been obtained in vitro on this dye as a membrane/lipophilic probe and as a peptide fluorescent label.

  DOI：

  10.1021/acs.joc.5b02066
• 作为产物：
  描述：

  6-硝基吲哚 、 苯磺酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以96%的产率得到6-nitro-1-(phenylsulfonyl)-1H-indole
  参考文献：
  名称：

  MediaChrom: Discovering a Class of Pyrimidoindolone-Based Polarity-Sensitive Dyes

  摘要：

  A small library of six polarity-sensitive fluorescent dyes, nicknamed MediaChrom, was prepared. This class of dyes is characterized by a pyrimidoindolone core fitted out with a conjugated push pull system and a carboxy linker for a conceivable coupling with biomolecules. The optimized eight-step synthetic strategy involves a highly chemo- and regioselective gold-catalyzed cycloisomerization reaction. The photophysical properties of MediaChrom dyes have been evaluated in-depth. In particular, the MediaChrom bearing a diethylamino as an electron-donating group and a trifluormethyl as an electron-withdrawing group displays the most interesting and advantageous spectroscopic features (e.g., absorption and emission in the visible range and a good quantum yield). Promising results in terms of sensitivity have been obtained in vitro on this dye as a membrane/lipophilic probe and as a peptide fluorescent label.

  DOI：

  10.1021/acs.joc.5b02066

文献信息

• [EN] SYNTHESIS, PHARMACOLOGY AND USE OF NEW AND SELECTIVE FMS-LIKE TYROSINE KINASE 3 (FLT3) FLT3 INHIBITORS<br/>[FR] SYNTHÈSE, PHARMACOLOGIE ET UTILISATION DE NOUVEAUX INHIBITEURS SÉLECTIFS DE LA TYROSINE KINASE 3 DE TYPE FMS FLT3 (FLT3)
  申请人：UNIV REGENSBURG

  公开号：WO2019034538A1

  公开（公告）日：2019-02-21

  The present invention relates to small molecule compounds of formula (I) and their use as FLT3 inhibitors for the treatment of various diseases, such as acute myeloid leukemia (AML). The present invention further relates to methods of synthesizing the compounds and methods of treatment.

  本发明涉及式(I)的小分子化合物及其作为FLT3抑制剂用于治疗各种疾病，如急性髓系白血病（AML）。本发明还涉及合成这些化合物的方法和治疗方法。
• Synthesis, pharmacology and use of new and selective FMS-like tyrosine kinase 3 (FLT3) FLT3 inhibitors
  申请人：UNIVERSITÄT REGENSBURG

  公开号：US11384076B2

  公开（公告）日：2022-07-12

  The present invention relates to small molecule compounds of formula (I) and their use as FLT3 inhibitors for the treatment of various diseases, such as acute myeloid leukemia (AML). The present invention further relates to methods of synthesizing the compounds and methods of treatment.

  本发明涉及式（I）的小分子化合物及其作为FLT3抑制剂用于治疗各种疾病，如急性髓性白血病（AML）。本发明进一步涉及化合物的合成方法和治疗方法。
• Synthesis and Reactions of N-Protected 3-Nitroindoles
  作者：Erin T. Pelkey

  DOI：10.1055/s-1999-3512

  日期：1999.7
• CAIXACH J.; CAPELL R.; GALVEZ C.; GONZALEZ A.; ROCA N., J. HETEROCYCL. CHEM., 1979, 16, NO 8, 1631-1635
  作者：CAIXACH J.、 CAPELL R.、 GALVEZ C.、 GONZALEZ A.、 ROCA N.

  DOI：——

  日期：——
• Catalytic, dearomative 2,3-difluorination of indoles
  作者：Fang-Hai Tu、Shuang Lin、Ya-Jie Tang、Li-Cai Liu、Qingjiang Li、Honggen Wang

  DOI：10.1016/j.tchem.2023.100052

  日期：2023.12