5-Piperazin-1-ylindoline-2,3-dione | 1587732-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5-Piperazin-1-ylindoline-2,3-dione
• 英文别名: 5-piperazin-1-yl-1H-indole-2,3-dione
• CAS: 1587732-63-5
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: VPQHXHQBQSADIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  哌嗪 、 5-溴靛红 在 palladium diacetate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 5-Piperazin-1-ylindoline-2,3-dione
  参考文献：
  名称：

  Discovery and Structure Optimization of a Series of Isatin Derivatives asMycobacterium tuberculosisChorismate Mutase Inhibitors

  摘要：

  In this study, the crystal structure of the Mycobacterium tuberculosis (MTB) enzyme chorismate mutase (CM) bound to transition state analogue (PDB: 2FP2) was used as a framework for virtual screening of the BITS‐Pilani in‐house database (2500 compounds) to identify new scaffold. We identified isatin as novel small molecule MTB CM inhibitors; further twenty‐four isatin derivatives were synthesized and evaluated in vitro for their ability to inhibit MTB CM, and activity against M. tuberculosis as steps towards the derivation of structure–activity relationships (SAR) and lead optimization. Compound 3‐(4‐nitrobenzylidene)indolin‐2‐one, 24 emerged as the most promising lead with an IC50 of 1.01 ± 0.22 μm for purified CM and MIC of 23.5 μm for M. tuberculosis, with little or no cytotoxicity.

  DOI：

  10.1111/cbdd.12265

文献信息

• Discovery and Structure Optimization of a Series of Isatin Derivatives as<i>Mycobacterium tuberculosis</i>Chorismate Mutase Inhibitors
  作者：Variam U. Jeankumar、Reshma Alokam、Jonnalagadda P. Sridevi、Priyanka Suryadevara、Siddharth S. Matikonda、Santosh Peddi、Seedarala Sahithi、Mallika Alvala、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1111/cbdd.12265

  日期：2014.4

  In this study, the crystal structure of the Mycobacterium tuberculosis (MTB) enzyme chorismate mutase (CM) bound to transition state analogue (PDB: 2FP2) was used as a framework for virtual screening of the BITS‐Pilani in‐house database (2500 compounds) to identify new scaffold. We identified isatin as novel small molecule MTB CM inhibitors; further twenty‐four isatin derivatives were synthesized and evaluated in vitro for their ability to inhibit MTB CM, and activity against M. tuberculosis as steps towards the derivation of structure–activity relationships (SAR) and lead optimization. Compound 3‐(4‐nitrobenzylidene)indolin‐2‐one, 24 emerged as the most promising lead with an IC50 of 1.01 ± 0.22 μm for purified CM and MIC of 23.5 μm for M. tuberculosis, with little or no cytotoxicity.