1-(4-diethylamino-but-2-ynyl)-5-methyl-1H-indole-2,3-dione | 1575882-06-2

• 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: 1-(4-diethylamino-but-2-ynyl)-5-methyl-1H-indole-2,3-dione
• 英文别名: 1-(4-diethylaminobut-2-ynyl)-5-methyl-1H-indole-2,3-dione
• CAS: 1575882-06-2
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: WYWUFSVLRNYUSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-甲基靛红 在 sodium hydride 、 copper(l) chloride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.17h， 生成 1-(4-diethylamino-but-2-ynyl)-5-methyl-1H-indole-2,3-dione
  参考文献：
  名称：

  N-Propargylated isatin-Mannich mono- and bis-adducts: Synthesis and preliminary analysis of in vitro activity against Tritrichomonas foetus

  摘要：

  Cu(I)Cl promoted synthesis of N-propargylated-isatin Mannich mono- and bis-adducts with an extension towards the synthesis of N-propargylated-isatin-7-chloroquinoline conjugates was described. The synthesized scaffolds were evaluated for their in vitro activity against the veterinary protozoal pathogen Tritrichomonas foetus and cytotoxicity against human prostate (PC-3) cancer cell line. The preliminary evaluation data revealed the enhancement in the activity profiles with the introduction of 7-chloroquinoline ring with the most active conjugates 7a, 7c and 7d exhibiting an IC50 of 22.2, 11.3 and 24.5 mu M respectively against T. foetus and minimal toxicity against human prostate (PC-3) cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.015

文献信息

• Cu(I)Cl-promoted synthesis of novel N-alkylated isatin analogs with an extension toward isatin-4-aminoquinoline conjugates: in vitro analysis against Trichomonas vaginalis
  作者：Nisha、Richard Tran、Donald Yang、Dominique Hall、Melissa J. Hopper、Lisa A. Wrischnik、Kirkwood M. Land、Vipan Kumar

  DOI：10.1007/s00044-014-1024-y

  日期：2014.10

  Trichomonas vaginalis, the causative agent of trichomonosis, is the most common non-viral sexually transmitted disease. Infection with this protozoan may have serious consequences, especially for women. Currently, 5-nitroimidazole drugs are the treatment of choice for trichomonosis, but the emergence of drug resistant isolates has limited the effectiveness of this therapy. In this context, a library of isatin-mannich adducts and 4-aminoquinoline-isatin mannich conjugates was synthesized following the Cu-promoted Mannich reaction and evaluated for their preliminary in vitro analysis against T. vaginalis at 50 mu M. The preliminary evaluation data revealed that the introduction of 4-aminoquinoline ring enhanced the activity profiles with compounds viz. 6a and 6c exhibiting percentage growth inhibition of 92.13 and 100 %, respectively. Compounds with high levels of potency were further analyzed to determine their IC50 values as well as cytotoxicity profiles against mammalian cells. The most active compound in the synthesized conjugates displayed an IC50 value of 23 mu M against cultured G3 strain in TYM Diamond's media of T. vaginalis and was non-toxic to cultured mammalian HeLa cells at the same concentration.