1-[2-(2,4-dimethyl-5-oxo-2,5-dihydro-thiophen-3-yloxy)-ethyl]-5-fluoro-1H-indole-2,3-dione | 1292322-53-2

• 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-[2-(2,4-dimethyl-5-oxo-2,5-dihydro-thiophen-3-yloxy)-ethyl]-5-fluoro-1H-indole-2,3-dione
• 英文别名: 1-[2-[(2,4-dimethyl-5-oxo-2H-thiophen-3-yl)oxy]ethyl]-5-fluoroindole-2,3-dione
• CAS: 1292322-53-2
• 化学式: C₁₆H₁₄FNO₄S
• 分子量: 335.356
• InChiKey: SWOPJCXOATZWAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-溴乙基)-5-氟二氢吲哚-2,3-二酮 、 3,5-dimethylthiotetronic acid 在 potassium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 1-[2-(2,4-dimethyl-5-oxo-2,5-dihydro-thiophen-3-yloxy)-ethyl]-5-fluoro-1H-indole-2,3-dione
  参考文献：
  名称：

  Novel thiolactone–isatin hybrids as potential antimalarial and antitubercular agents

  摘要：

  The synthesis of a novel series of thiolactone-isatin hybrids led to the discovery of tetracyclic by-products which displayed superior antiplasmodial activity. The tetracycles thus formed the basis of a more focused SAR study. Identified from this series is a compound with an IC50 of 6.92 mu M against the chloroquine-resistant (W2) strain of Plasmodium falciparum. Useful antimalarial SARs delineated include the need for substitution at C-5 of the isatin scaffold and the enhancement of activity by increasing the linker length. In contrast to their antimalarial activity, the tetracycles were devoid of antitubercular activity whereas the advanced intermediates displayed growth inhibitory activity against the H(37)Rv strain of Mycobacterium tuberculosis as revealed by BACTEC, MABA and LORA assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.008

文献信息

• Novel thiolactone–isatin hybrids as potential antimalarial and antitubercular agents
  作者：Renate H. Hans、Ian J.F. Wiid、Paul D. van Helden、Baojie Wan、Scott G. Franzblau、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmcl.2011.02.008

  日期：2011.4

  The synthesis of a novel series of thiolactone-isatin hybrids led to the discovery of tetracyclic by-products which displayed superior antiplasmodial activity. The tetracycles thus formed the basis of a more focused SAR study. Identified from this series is a compound with an IC50 of 6.92 mu M against the chloroquine-resistant (W2) strain of Plasmodium falciparum. Useful antimalarial SARs delineated include the need for substitution at C-5 of the isatin scaffold and the enhancement of activity by increasing the linker length. In contrast to their antimalarial activity, the tetracycles were devoid of antitubercular activity whereas the advanced intermediates displayed growth inhibitory activity against the H(37)Rv strain of Mycobacterium tuberculosis as revealed by BACTEC, MABA and LORA assays. (C) 2011 Elsevier Ltd. All rights reserved.