1-(2-thioxothiazolidin-3-yl)pentane-1,4-dione | 1384959-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 1-(2-thioxothiazolidin-3-yl)pentane-1,4-dione
• 英文别名: 1-(2-Sulfanylidene-1,3-thiazolidin-3-yl)pentane-1,4-dione；1-(2-sulfanylidene-1,3-thiazolidin-3-yl)pentane-1,4-dione
• CAS: 1384959-14-1
• 化学式: C₈H₁₁NO₂S₂
• 分子量: 217.313
• InChiKey: NQIXGPZEKBFDAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-thioxothiazolidin-3-yl)pentane-1,4-dione 、 [3-(吖啶-9-基氨基)-5-氨基苯基]甲醇 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到3-(9-acridinylamino)-5-hydroxymethyl-N-acetonylacetylaniline
  参考文献：
  名称：

  Polymer conjugates of acridine-type anticancer drugs with pH-controlled activation

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2012.05.007
• 作为产物：
  描述：

  2-巯基噻唑啉 、 乙酰丙酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 1-(2-thioxothiazolidin-3-yl)pentane-1,4-dione
  参考文献：
  名称：

  PEPTIDE-BASED VACCINES, METHODS OF MANUFACTURING, AND USES THEREOF FOR INDUCING AN IMMUNE RESPONSE

  摘要：

  本公开涉及新型基于肽的疫苗，制造该新型基于肽的疫苗的方法以及将其用于传递肽抗原以诱导免疫应答，特别是T细胞应答给受试者。

  公开号：

  US20200054741A1

文献信息

• Synthesis of Poly[<i>N</i>-(2-hydroxypropyl)methacrylamide] Conjugates of Inhibitors of the ABC Transporter That Overcome Multidrug Resistance in Doxorubicin-Resistant P388 Cells in Vitro
  作者：V. Šubr、L. Sivák、E. Koziolová、A. Braunová、M. Pechar、J. Strohalm、M. Kabešová、B. Říhová、K. Ulbrich、M. Kovář

  DOI：10.1021/bm500649q

  日期：2014.8.11

  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.
• PEPTIDE-BASED VACCINES, METHODS OF MANUFACTURING, AND USES THEREOF FOR INDUCING AN IMMUNE RESPONSE
  申请人：Avidea Technologies, Inc.

  公开号：US20200054741A1

  公开（公告）日：2020-02-20

  The present disclosure relates to novel peptide-based vaccines, methods of manufacturing the novel peptide-based vaccines and uses thereof for delivering peptide antigens to induce an immune response, and in particular a T cell response to a subject.

  本公开涉及新型基于肽的疫苗，制造该新型基于肽的疫苗的方法以及将其用于传递肽抗原以诱导免疫应答，特别是T细胞应答给受试者。
• 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.