4,5-dihydro-5-(3-methyl-2(3H)-benzothiazolylidene)-2-methylthio-3-benzyl-4-oxothiazolium p-toluenesulfonate

• 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: 4,5-dihydro-5-(3-methyl-2(3H)-benzothiazolylidene)-2-methylthio-3-benzyl-4-oxothiazolium p-toluenesulfonate
• 英文别名: 3-benzyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-methylthio-4-oxo-2-thiazolium p-toluenesulfonate；(5E)-3-benzyl-5-(3-methyl-1,3-benzothiazol-2-ylidene)-2-methylsulfanyl-1,3-thiazol-3-ium-4-one;4-methylbenzenesulfonate
• 化学式: C₇H₇O₃S*C₁₉H₁₇N₂OS₃
• 分子量: 556.752
• InChiKey: AEFNGZPWRVEQHQ-HYNBPGMHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-5-(3-methyl-2(3H)-benzothiazolylidene)-2-methylthio-3-benzyl-4-oxothiazolium p-toluenesulfonate 、 1,2-dimethylpyridinium p-toluenesulfonate 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 2-[{5-(3-methyl-2(3H)-benzothiazolylidene)-4-oxo-3-benzyl-2-thiazolidinylidene}methyl]-1-methylpyridinium p-toluenesulfonate
  参考文献：
  名称：

  Rhodacyanine Dyes as Antimalarials. 1. Preliminary Evaluation of Their Activity and Toxicity

  摘要：

  The rhodacyanine dye MKT-077 (1), a potent antitumor agent, was found to possess strong in vitro activity against Plasmodium falciparum and a low cytotoxicity. Several new rhodacyanine dyes related to 1, containing a variety of linked heterocyclic moieties, were synthesized, and their antimalarial potencies were evaluated. The synthetic rhodacyanines were found to have EC50 values against P. falciparum in vitro in the range of 4-300 nM. Several compounds in this series have remarkable selective toxicity profiles (> 100).

  DOI：

  10.1021/jm0155704
• 作为产物：
  描述：

  2-甲硫基苯并噻唑 在 三乙胺 作用下， 以 苯甲醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 4,5-dihydro-5-(3-methyl-2(3H)-benzothiazolylidene)-2-methylthio-3-benzyl-4-oxothiazolium p-toluenesulfonate
  参考文献：
  名称：

  Rhodacyanine Dyes as Antimalarials. 1. Preliminary Evaluation of Their Activity and Toxicity

  摘要：

  The rhodacyanine dye MKT-077 (1), a potent antitumor agent, was found to possess strong in vitro activity against Plasmodium falciparum and a low cytotoxicity. Several new rhodacyanine dyes related to 1, containing a variety of linked heterocyclic moieties, were synthesized, and their antimalarial potencies were evaluated. The synthetic rhodacyanines were found to have EC50 values against P. falciparum in vitro in the range of 4-300 nM. Several compounds in this series have remarkable selective toxicity profiles (> 100).

  DOI：

  10.1021/jm0155704

文献信息

• Heterocyclic modulators of nuclear receptors
  申请人：——

  公开号：US20030212111A1

  公开（公告）日：2003-11-13

  Compounds, compositions and methods for modulating the activity of nuclear receptors are provided. In particular, heterocyclic compounds are provided for modulating the activity of farnesoid X receptor (FXR), liver X receptor (LXR) and/or orphan nuclear receptors. In certain embodiments, the compounds are thiazolidinone derivatives.

  提供了用于调节核受体活性的化合物、组合物和方法。具体来说，提供了用于调节法尼索醇X受体（FXR）、肝X受体（LXR）和/或孤儿核受体活性的杂环化合物。在某些实施例中，这些化合物是噻唑啉酮衍生物。
• EP1623981
  申请人：——

  公开号：——

  公开（公告）日：——
• Analogues of the Allosteric Heat Shock Protein 70 (Hsp70) Inhibitor, MKT-077, As Anti-Cancer Agents
  作者：Xiaokai Li、Sharan R. Srinivasan、Jamie Connarn、Atta Ahmad、Zapporah T. Young、Adam M. Kabza、Erik. R. P. Zuiderweg、Duxin Sun、Jason E. Gestwicki

  DOI：10.1021/ml400204n

  日期：2013.11.14

  The rhodacyanine, MKT-077, has antiproliferative activity against cancer cell lines through its ability to inhibit members of the heat shock protein 70 (Hsp70) family of molecular chaperones. However, MKT-077 is rapidly metabolized, which limits its use as either a chemical probe or potential therapeutic. We report the synthesis and characterization of MKT-077 analogues designed for greater stability. The most potent molecules, such as 30 (JG-98), were at least 3-fold more active than MKT-077 against the breast cancer cell lines MDA-MB-231 and MCF-7 (EC50 values of 0.4 +/- 0.03 and 0.7 +/- 0.2 mu M, respectively). The analogues modestly destabilized the chaperone clients, Aka and Raf1, and induced apoptosis in these cells. Further, the microsomal half-life of JG-98 was improved at least 7-fold (t(1/2) = 37 min) compared to MKT-077 (t(1/2) < 5 min). Finally, NMR titration experiments suggested that these analogues bind an allosteric site that is known to accommodate MKT-077. These studies advance MKT-077 analogues as chemical probes for studying Hsp70s roles in cancer.
• Rhodacyanine Dyes as Antimalarials. 1. Preliminary Evaluation of Their Activity and Toxicity
  作者：Kiyosei Takasu、Hiroshi Inoue、Hye-Sook Kim、Makoto Suzuki、Tadao Shishido、Yusuke Wataya、Masataka Ihara

  DOI：10.1021/jm0155704

  日期：2002.2.1

  The rhodacyanine dye MKT-077 (1), a potent antitumor agent, was found to possess strong in vitro activity against Plasmodium falciparum and a low cytotoxicity. Several new rhodacyanine dyes related to 1, containing a variety of linked heterocyclic moieties, were synthesized, and their antimalarial potencies were evaluated. The synthetic rhodacyanines were found to have EC50 values against P. falciparum in vitro in the range of 4-300 nM. Several compounds in this series have remarkable selective toxicity profiles (> 100).