5-(3-methyl-(3H)-benzothiazol-2-ylidene)-3-(2-propenyl)-2-thioxo-4-thiazolidinone | 41504-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 5-(3-methyl-(3H)-benzothiazol-2-ylidene)-3-(2-propenyl)-2-thioxo-4-thiazolidinone
• 英文别名: N-Ethyl-5-<1-methyl-1,2-dihydro-benzothiazolyliden-(2)-rhodanin；5-(3-methyl-(3H)-benzothiazol-2-ylidene)-3-ethyl-2-thioxo-4-thiazolidinone；3-ethyl-5-(3-methyl-3H-benzothiazol-2-ylidene)-2-thioxo-thiazolidin-4-one；3-Aethyl-5-(3-methyl-3H-benzothiazol-2-yliden)-2-thioxo-thiazolidin-4-on；5-(3-Methyl-2-(3H)benzothiazolinylidene)-3-ethyl rhodanine；3-ethyl-5-(3-methyl-1,3-benzothiazol-2-ylidene)-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 41504-13-6
• 化学式: C₁₃H₁₂N₂OS₃
• 分子量: 308.449
• InChiKey: BXNZOCAILBRXHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  265 °C
• 沸点：
  351.9±52.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(3-methyl-(3H)-benzothiazol-2-ylidene)-3-(2-propenyl)-2-thioxo-4-thiazolidinone 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.5h， 生成 2-[3-ethyl-5-(3-methyl-(3H)-benzothiazol-2-ylidene)-4-oxothiazolidin-2-ylidenemethyl]-3-methyl benzothiazolium 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 、 乙腈 为溶剂， 反应 5.0h， 生成 5-(3-methyl-(3H)-benzothiazol-2-ylidene)-3-(2-propenyl)-2-thioxo-4-thiazolidinone
  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

• Design, synthesis and biological evaluation of new rhodacyanine analogues as potential antitumor agents
  作者：Yang Xiong Li、Xin Zhai、Wei Ke Liao、Wu Fu Zhu、Ying He、Ping Gong

  DOI：10.1016/j.cclet.2012.01.015

  日期：2012.4

  attempt to develop potent antitumor agents, new rhodacyanine analogues containing the pyridinium ring ( 5a – 5h ), the isoquinolinium ring ( 6a – 6c ) and the quinolinium ring ( 7a – 7e ) linked to the rhodanine ring via N–N covalent bond were designed, synthesized and evaluated for antitumor activity against human lung cancer cell line (H460) by MTT assay in vitro . Most of the tested compounds showed enhanced

  摘要为了开发有效的抗肿瘤药物，新的含有酪氨酸环（5a-5h），异喹啉鎓环（6a-6c）和喹啉鎓环（7a-7e）的若丹菁类似物通过N–N共价键与罗丹宁环连接通过MTT法体外设计，合成并评价了对人肺癌细胞系（H460）的抗肿瘤活性。与先导化合物MKT-077相比，大多数测试化合物显示出增强的抗肿瘤活性，IC 50值为0.006至9.2μmol/ L。其中，最有前途的化合物7d（IC 50 = 0.006μmol/ L）的活性是MKT-077（IC 50 = 1.3μmol/ L）的216.7倍。讨论了目标化合物的初步结构-活性关系。
• Heterocyclic modulators of nuclear receptors
  申请人：X-Ceptor Therapeutics, Inc.

  公开号：US07115640B2

  公开（公告）日：2006-10-03

  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。特别地，提供了用于调节法尼酰二烯醇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，这些化合物为噻唑烷酮衍生物。
• Anti-leishmania agent
  申请人：Ihara Masataka

  公开号：US20060252800A1

  公开（公告）日：2006-11-09

  The present invention is to provide a new anti- leishmania agent with fewer side effects, having a high cell proliferation-inhibiting effect to leishamia protozoa, and also easy to manufacture at a low cost. A compound wherein a heterocycle with a conjugated system and a nitrogen atom and a heterocycle with a nitrogen atom and a sulfur atom are bound by a carbon chain with an ethylene group, that is a compound wherein a specific 5- to 8-membered heterocyclic ring and a specific 5- to 8-membered heterocycle having a conjugated system are bound via a vinylene group, more particularly a specific rhodacyanine dye compound is used as an active ingredient of the anti- leishmania agent.

  本发明旨在提供一种新的抗利什曼原虫药物，具有较少的副作用，对利什曼原虫具有高细胞增殖抑制作用，并且易于低成本制造。该化合物由具有共轭系统和氮原子的杂环和具有氮原子和硫原子的杂环通过碳链和乙烯基结合而成，即通过乙烯基将特定的5-8成员杂环和具有共轭系统的特定的5-8成员杂环结合在一起，更具体地，使用特定的铑青菁染料化合物作为抗利什曼原虫药物的活性成分。
• Meerwein,H. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 641, p. 1 - 39
  作者：Meerwein,H. et al.

  DOI：——

  日期：——
• 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。