5-(3-methyl-(3H)-benzothiazol-2-ylidene)-2-methylsulfanyl-4-oxo-4,5-dihydrothiazol-3-ium 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: 5-(3-methyl-(3H)-benzothiazol-2-ylidene)-2-methylsulfanyl-4-oxo-4,5-dihydrothiazol-3-ium p-toluenesulfonate
• 英文别名: 3-Ethyl-5-(3-methyl-1,3-benzothiazol-2-ylidene)-2-methylsulfanyl-1,3-thiazol-3-ium-4-one;4-methylbenzenesulfonate；3-ethyl-5-(3-methyl-1,3-benzothiazol-2-ylidene)-2-methylsulfanyl-1,3-thiazol-3-ium-4-one;4-methylbenzenesulfonate
• 化学式: C₇H₇O₃S*C₁₄H₁₅N₂OS₃
• 分子量: 494.681
• InChiKey: ZKBPTHOQNINQOD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  5-(3-methyl-(3H)-benzothiazol-2-ylidene)-2-methylsulfanyl-4-oxo-4,5-dihydrothiazol-3-ium p-toluenesulfonate 、 1,4-dimethylquinolinium iodide 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以0.23 g的产率得到4-[3-ethyl-5-(3-methyl-(3H)-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylidenemethyl]-1-methyl quinolinium iodide
  参考文献：
  名称：

  Synthesis, spectral properties of rhodanine complex merocyanine dyes as well as their effect on K562 leukemia cells

  摘要：

  Two rhodanine complex merocyanine dyes 9a and 9b were synthesized and their structures were confirmed by H-1 NMR, IR, MS, HRMS and UV-Vis spectra. From the spectral properties of the two dyes, it could be found that the lambda(max) of the dyes showed hypsochromic shifts with the increase of permittivity in protonic solvents, and bathochromic shifts with the increase of refractive index in non protonic solvents. The interactions of two dyes with DNA or BSA were also studied under physiological conditions. The results showed that the quantum yield of DNA-dye 9a was up to 29.5 times compared with free dye 9a. Dyes 9a and 9b were researched in Photodynamic Therapy (PDT) as well. It was demonstrated that supplementation of dye 9a or 9b as photosensitizers for PDT in K562 cells decreases the survival rate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2011.10.017
• 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 8.0h， 生成 5-(3-methyl-(3H)-benzothiazol-2-ylidene)-2-methylsulfanyl-4-oxo-4,5-dihydrothiazol-3-ium p-toluenesulfonate
  参考文献：
  名称：

  三种类别的若丹菁染料的合成及其对体外和体内抗疟活性的评估。

  摘要：

  合成了三类罗丹菁染料[0,0]-，[1,0]-和[0,0,0]-罗丹菁的选定成员，它们对恶性疟原虫K1具有体外抗疟活性（对氯喹有抗性）确定了它们在小鼠中的抗性以及它们对伯氏疟原虫的体内活性。具有苯并噻唑部分的新型[0,0,0]-罗丹嘧啶3e和3h已显示出在体内具有非常有前途的抗疟活性。此外，发现[0,0,0]-罗丹菁是口服生物利用度的。

  DOI：

  10.1016/j.bmc.2006.08.035

文献信息

• Synthesis of three classes of rhodacyanine dyes and evaluation of their in vitro and in vivo antimalarial activity
  作者：Khanitha Pudhom、Kazuki Kasai、Hiroki Terauchi、Hiroshi Inoue、Marcel Kaiser、Reto Brun、Masataka Ihara、Kiyosei Takasu

  DOI：10.1016/j.bmc.2006.08.035

  日期：2006.12

  0]-rhodacyanines, were synthesized and their in vitro antimalarial activities against Plasmodium falciparum K1 (chloroquine-resistant strain) as well as their in vivo activities against P. berghei in mice were determined. The novel [0,0,0]-rhodacynines, 3e and 3h, possessing a benzothiazole moiety, were shown to have highly promising antimalarial activities in vivo. Moreover, the [0,0,0]-rhodacyanines were found

  合成了三类罗丹菁染料[0,0]-，[1,0]-和[0,0,0]-罗丹菁的选定成员，它们对恶性疟原虫K1具有体外抗疟活性（对氯喹有抗性）确定了它们在小鼠中的抗性以及它们对伯氏疟原虫的体内活性。具有苯并噻唑部分的新型[0,0,0]-罗丹嘧啶3e和3h已显示出在体内具有非常有前途的抗疟活性。此外，发现[0,0,0]-罗丹菁是口服生物利用度的。
• 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酰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，这些化合物是噻唑烷酮衍生物。
• Synthesis, spectral properties of rhodanine complex merocyanine dyes as well as their effect on K562 leukemia cells
  作者：Jun-Feng Xiang、Yan-Xia Liu、Dan Sun、Su-Juan Zhang、Yi-Le Fu、Xiang-Han Zhang、Lan-Ying Wang

  DOI：10.1016/j.dyepig.2011.10.017

  日期：2012.4

  Two rhodanine complex merocyanine dyes 9a and 9b were synthesized and their structures were confirmed by H-1 NMR, IR, MS, HRMS and UV-Vis spectra. From the spectral properties of the two dyes, it could be found that the lambda(max) of the dyes showed hypsochromic shifts with the increase of permittivity in protonic solvents, and bathochromic shifts with the increase of refractive index in non protonic solvents. The interactions of two dyes with DNA or BSA were also studied under physiological conditions. The results showed that the quantum yield of DNA-dye 9a was up to 29.5 times compared with free dye 9a. Dyes 9a and 9b were researched in Photodynamic Therapy (PDT) as well. It was demonstrated that supplementation of dye 9a or 9b as photosensitizers for PDT in K562 cells decreases the survival rate. (C) 2011 Elsevier Ltd. All rights reserved.