1-[4-(2-thioxo-thiazolidine-3-carbonyl)-phenyl]-propan-2-one | 1384959-15-2

• 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: 1-[4-(2-thioxo-thiazolidine-3-carbonyl)-phenyl]-propan-2-one
• 英文别名: 1-[4-(2-thioxothiazolidine-3-carbonyl)phenyl]propan-2-one
• CAS: 1384959-15-2
• 化学式: C₁₃H₁₃NO₂S₂
• 分子量: 279.384
• InChiKey: HOPMRXVHYDLQQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[4-(2-thioxo-thiazolidine-3-carbonyl)-phenyl]-propan-2-one 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Poly[N-(2-hydroxypropyl)methacrylamide] Conjugates of Inhibitors of the ABC Transporter That Overcome Multidrug Resistance in Doxorubicin-Resistant P388 Cells in Vitro

  摘要：

  The effects of novel polymeric therapeutics based on water-soluble N-(2-hydroxypropyl)methacrylamide copolymers (P(HPMA)) bearing the anticancer drug doxorubicin (Dox), an inhibitor of ABC transporters, or both, on the viability and the proliferation of the murine monocytic leukemia cell line P388 (parental cell line) and its doxorubicin-resistant subline P388/MDR were studied in vitro. The inhibitor derivatives 5-methyl-4-oxohexanoyl reversin 121 (MeOHe-R121) and 5-methyl-4-oxohexanoyl ritonavir ester (MeOHe-RIT), showing the highest inhibitory activities, were conjugated to the P(HPMA) via the biodegradable pH-sensitive hydrazone bond, and the ability of these conjugates to block the ATP driven P-glycoprotein (P-gp) efflux pump was tested. The P(HPMA) conjugate P-Ahx-NH-N═MeOHe-R121 showed a dose-dependent increase in the ability to sensitize the P388/MDR cells to Dox from 1.5 to 24 μM, and achieved an approximately 50-fold increase in sensitization at 24 μM. The P(HPMA) conjugate P-Ahx-NH-N═MeOHe-RIT showed moderate activity at 6 μM (∼10 times higher sensitization) and increased sensitization by 50-fold at 12 μM. The cytostatic activity of the P(HPMA) conjugate P-Ahx-NH-N═MeOHe-R121(Dox) containing Dox and the P-gp inhibitor MeOHe-R121, both bound via hydrazone bonds to the P(HPMA) carrier, was almost 30 times higher than that of the conjugate P-Ahx-NH-N═Dox toward the P388/MDR cells in vitro. A similar result was observed for P-Ahx-NH-N═MeOHe-RIT(Dox), which exhibited almost 10 times higher cytostatic activity than P-Ahx-NH-N═Dox.

  DOI：

  10.1021/bm500649q
• 作为产物：
  描述：

  2-巯基噻唑啉 、 4-(2-oxopropyl)benzoic acid 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 1-[4-(2-thioxo-thiazolidine-3-carbonyl)-phenyl]-propan-2-one
  参考文献：
  名称：

  [EN] FLUORESCENTLY LABELLED POLYMER FOR TUMOUR VISUALIZATION, METHOD OF ITS PREPARATION AND USE THEREOF
  [FR] POLYMÈRE MARQUÉ PAR FLUORESCENCE POUR VISUALISATION DE TUMEURS, SON PROCÉDÉ DE PRÉPARATION ET SON UTILISATION

  摘要：

  The present invention relates to a fluorescently labelled polymer, to which a fluorescent label is bound in an amount of from 0.1 to 10 mol %, related to the total number of monomer units. The fluorescence of said polymer is activated in tumour tissue, therefore a significant visualization of tumour tissue is provided. It may therefore be used in diagnostic methods or image-guided surgery. Preferably, the fluorescently labelled polymer is targeted towards tumour cells and tumour neovasculature using specific targeting groups. The present invention further relates to methods of preparation of the fluorescently labelled polymer, and its use as a fluorescence probe in diagnostic methods as a contrast agent for tumour visualization, whole body imaging and/or for image-guided surgery.

  公开号：

  WO2023036351A1

文献信息

• Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation
  作者：Ondřej Sedláček、Martin Hrubý、Martin Studenovský、David Větvička、Jan Svoboda、Dana Kaňková、Jan Kovář、Karel Ulbrich

  DOI：10.1016/j.bmc.2012.05.007

  日期：2012.7

  Acridines are potent DNA-intercalating anticancer agents with high in vivo anticancer effectiveness, but also severe side effects. We synthesized five 9-anilinoacridine-type drugs and their conjugates with biocompatible water-soluble hydrazide polymer carrier. All of the synthesized acridine drugs retained their in vitro antiproliferative properties. Their polymer conjugates were sufficiently stable at pH 7.4 (model of pH in blood plasma) while releasing free drugs at pH 5.0 (model of pH in endosomes). After internalization of the conjugates, the free drugs were released and are visible in cell nuclei by fluorescence microscopy. Their intercalation ability was proven using a competitive ethidium bromide displacement assay. (C) 2012 Elsevier Ltd. All rights reserved.