4-(2-azido-ethyl)-3-(3-fluoro-benzenesulfonyl)-1H-indole | 945000-93-1

• 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-(2-azido-ethyl)-3-(3-fluoro-benzenesulfonyl)-1H-indole
• 英文别名: 4-(2-azidoethyl)-3-(3-fluorophenyl)sulfonyl-1H-indole
• CAS: 945000-93-1
• 化学式: C₁₆H₁₃FN₄O₂S
• 分子量: 344.369
• InChiKey: SOXWGARGLBDUIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-azido-ethyl)-3-(3-fluoro-benzenesulfonyl)-1H-indole 、 FMOC-beta-丙氨酸 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 2-[4-[(4-Aminobutylamino)methyl]phenoxy]anthracene-1,4-dione;2,2,2-trifluoroacetic acid
  参考文献：
  名称：

  Conjugation of Quinones with Natural Polyamines: Toward an Expanded Antitrypanosomatid Profile

  摘要：

  A combinatorial library of quinone-polyamine conjugates designed to optimize the antitrypanosomatid profile of hit compounds 1 and 2 has been prepared by a solid-phase approach. The conjugates were evaluated against the three most important human trypanosomatid pathogens (Trypanosoma brucei rhodesiense, Trypanosoma cruzi, and Leishmania donovani), and several showed promising activity. A subset also inhibited trypanothione reductase in vitro and induced oxidase activity of the enzyme. A highly potent analogue (7) was identified with activity against T. brucei as low as 70 nM and a selectivity index of 72. Interestingly, the presence of a cadaverine tail confers to 7 the ability to target mitochondrial function in Leishmania. In fact, in L. donovani promastigotes, we verified for 7 a decrease of cytoplasmic ATP and mitochondrial potential. Therefore, the current results support the suitability of the conjugation approach for the development of novel polyamine conjugates with enhanced therapeutic potential.

  DOI：

  10.1021/jm301112z
• 作为产物：
  描述：

  1,3-丙二胺 、 trityl chloride polystyrene resin 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-(2-azido-ethyl)-3-(3-fluoro-benzenesulfonyl)-1H-indole
  参考文献：
  名称：

  WO2007/80109

  摘要：

  公开号：

文献信息

• Sulfonyl Substituted 1H-Indoles as Ligands for the 5-Hydroxytryptamine Receptors
  申请人：McDevitt Robert E.

  公开号：US20070203120A1

  公开（公告）日：2007-08-30

  The present invention is directed to compounds of Formula I: which are modulators of the 5-hydroxtryptamine-6 and 5-hydroxytryptamine-2A receptors and which are inhibitors of norepinephrine reuptake. The compounds of the invention, and pharmaceutical composition thereof, are useful in the treatment of disorders related to or associated with the 5-hydroxytryptamine-6 and 5-hydroxtryptamine-2A receptors or with norepinephrine reuptake inhibition.

  本发明涉及式I的化合物：它们是5-羟色胺-6和5-羟色胺-2A受体的调节剂，同时也是去甲肾上腺素再摄取抑制剂。本发明的化合物及其制药组合物在治疗与5-羟色胺-6和5-羟色胺-2A受体或去甲肾上腺素再摄取抑制有关或相关的疾病方面是有用的。
• SULFONYL SUBSTITUTED 1H-INDOLES AS LIGANDS FOR THE 5-HYDROXYTRYPTAMINE RECEPTORS
  申请人：Wyeth

  公开号：EP1973876A2

  公开（公告）日：2008-10-01
• US7645752B2
  申请人：——

  公开号：US7645752B2

  公开（公告）日：2010-01-12
• [EN] SULFONYL SUBSTITUTED 1H-INDOLES AS LIGANDS FOR THE 5-HYDROXYTRYPTAMINE RECEPTORS<br/>[FR] 1H-INDOLES SUBSTITUES PAR UN GROUPE SULFONYLE EN TANT QUE LIGANDS POUR LES RECEPTEURS DE LA 5-HYDROXYTRYPTAMINE
  申请人：WYETH CORP

  公开号：WO2007084841A2

  公开（公告）日：2007-07-26

  [EN] The present invention is directed to compounds of Formula I: which are modulators of the 5-hydroxtryptamine-6 and 5-hydroxytryptamine-2A receptors and which are inhibitors of norepinephrine reuptake. The compounds of the invention, and pharmaceutical composition thereof, are useful in the treatment of disorders related to or associated with the 5-hydroxytryptamine-6 and 5- hydroxtryptamine-2A receptors or with norepinephrine reuptake inhibition.
  [FR] La présente invention concerne des composés répondant à la formule I : qui sont des modulateurs des récepteurs de la 5-hydroxtryptamine-6 et de la 5-hydroxytryptamine-2A et qui sont des inhibiteurs de recapture de la norépinéphrine. Les composés de la présente invention, et la composition pharmaceutique de ceux-ci, sont utiles dans le traitement de troubles se rapportant ou associés aux récepteurs de la 5-hydroxtryptamine-6 et de la 5-hydroxytryptamine-2A ou à l'inhibition de la recapture de la norépinéphrine.