3-(4-Methoxybenzo[d]thiazol-2-yl)-2-(2,6-dichlorophenyl)thiazolidin-4-one (15) | 1421349-85-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 3-(4-Methoxybenzo[d]thiazol-2-yl)-2-(2,6-dichlorophenyl)thiazolidin-4-one (15)
• 英文别名: 2-(2,6-dichlorophenyl)-3-(4-methoxy-1,3-benzothiazol-2-yl)-1,3-thiazolidin-4-one
• CAS: 1421349-85-0
• 化学式: C₁₇H₁₂Cl₂N₂O₂S₂
• 分子量: 411.332
• InChiKey: QYHFUWPDBAVADE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基-4-甲氧基苯并噻唑 、 2,6-二氯苯甲醛 、 巯基乙酸 生成 3-(4-Methoxybenzo[d]thiazol-2-yl)-2-(2,6-dichlorophenyl)thiazolidin-4-one (15)
  参考文献：
  名称：

  Synthesis and HIV-1 RT inhibitory action of novel (4/6-substituted benzo[d]thiazol -2-yl)thiazolidin-4-ones. Divergence from the non-competitive inhibition mechanism

  摘要：

  Reverse transcriptase (RT) inhibitors play a major role in the therapy of human immunodeficiency virus type 1 (HIV-1) infection. Although, many compounds are already used as anti-HIV drugs, research on development of novel inhibitors continues, since drug resistant strains appear because of prolonged therapy. In this paper, we present the synthesis and evaluation of HIV-1 RT inhibitory action of eighteen novel (4/6-halogen/MeO/EtO-substituted benzo[d]thiazol-2-yl)thiazolidin-4-ones. The two more active compounds (IC50:0.04 mu M and 0.25 mu M) exhibited better inhibitory action than the reference compound, nevirapine. Docking analysis supports a stable binding of the most active derivative to the allosteric centre of RT. Kinetic analysis of two of the most active compounds indicate an uncompetitive inhibition mode. This is a desired characteristic, since mutations that affect activity of traditional non-competitive NNRTIs may not affect activity of compounds of this series. Interestingly, the less active derivatives (IC50 > 40 mu M) exhibit a competitive mode of action.

  DOI：

  10.3109/14756366.2011.636362

文献信息

• Synthesis and HIV-1 RT inhibitory action of novel (4/6-substituted benzo[d]thiazol -2-yl)thiazolidin-4-ones. Divergence from the non-competitive inhibition mechanism
  作者：Eleni Pitta、Athina Geronikaki、Sofiko Surmava、Phaedra Eleftheriou、Vaibhav P. Mehta、Erik V. Van der Eycken

  DOI：10.3109/14756366.2011.636362

  日期：2013.2.1

  Reverse transcriptase (RT) inhibitors play a major role in the therapy of human immunodeficiency virus type 1 (HIV-1) infection. Although, many compounds are already used as anti-HIV drugs, research on development of novel inhibitors continues, since drug resistant strains appear because of prolonged therapy. In this paper, we present the synthesis and evaluation of HIV-1 RT inhibitory action of eighteen novel (4/6-halogen/MeO/EtO-substituted benzo[d]thiazol-2-yl)thiazolidin-4-ones. The two more active compounds (IC50:0.04 mu M and 0.25 mu M) exhibited better inhibitory action than the reference compound, nevirapine. Docking analysis supports a stable binding of the most active derivative to the allosteric centre of RT. Kinetic analysis of two of the most active compounds indicate an uncompetitive inhibition mode. This is a desired characteristic, since mutations that affect activity of traditional non-competitive NNRTIs may not affect activity of compounds of this series. Interestingly, the less active derivatives (IC50 > 40 mu M) exhibit a competitive mode of action.