3-(2-methoxy-ethyl)-2-phenylimino-thiazolidin-4-one | 1147840-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(2-methoxy-ethyl)-2-phenylimino-thiazolidin-4-one
• 英文别名: 3-(2-Methoxyethyl)-2-phenylimino-1,3-thiazolidin-4-one
• CAS: 1147840-82-1
• 化学式: C₁₂H₁₄N₂O₂S
• 分子量: 250.321
• InChiKey: BWHUSLKKFQYSKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-methoxy-ethyl)-2-phenylimino-thiazolidin-4-one 、 2-氯-5-(5-甲酰基-2-呋喃基)苯甲酸甲酯 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以60.1%的产率得到2-chloro-5-{5-[3-(2-methoxy-ethyl)-4-oxo-2-phenylimino-thiazolidin-5-ylidenemethyl]-furan-2-yl}-benzoic acid methyl ester
  参考文献：
  名称：

  Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of Helicobacter pylori: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination

  摘要：

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

  DOI：

  10.1021/jm8015602
• 作为产物：
  描述：

  硫代异氰酸苯酯 在 sodium acetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 3-(2-methoxy-ethyl)-2-phenylimino-thiazolidin-4-one
  参考文献：
  名称：

  噻唑烷酮类免疫蛋白酶体抑制剂及其制法和药物用途

  摘要：

  本发明属于药物化学领域，公开了通式(I)所示新的噻唑烷酮类化合物及其立体异构体和生理上可接受的盐，所述化合物的制备方法，含有所述化合物的药物制剂，以及所述化合物在治疗与免疫蛋白酶体相关疾病中的临床应用。#imgabs0#

  公开号：

  CN117384150A

文献信息

• Discovering Potent Inhibitors Against the β-Hydroxyacyl-Acyl Carrier Protein Dehydratase (FabZ) of <i>Helicobacter pylori</i>: Structure-Based Design, Synthesis, Bioassay, and Crystal Structure Determination
  作者：Lingyan He、Liang Zhang、Xiaofeng Liu、Xianghua Li、Mingyue Zheng、Honglin Li、Kunqian Yu、Kaixian Chen、Xu Shen、Hualiang Jiang、Hong Liu

  DOI：10.1021/jm8015602

  日期：2009.4.23

  The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC(50) values less than 2 muM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC(50) = 0.86 muM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.
• 噻唑烷酮类免疫蛋白酶体抑制剂及其制法和药物用途
  申请人：中国医学科学院药物研究所

  公开号：CN117384150A

  公开（公告）日：2024-01-12

  本发明属于药物化学领域，公开了通式(I)所示新的噻唑烷酮类化合物及其立体异构体和生理上可接受的盐，所述化合物的制备方法，含有所述化合物的药物制剂，以及所述化合物在治疗与免疫蛋白酶体相关疾病中的临床应用。#imgabs0#