2,3-dimethylbenzoxazolium p-toluenesulphonate | 39759-82-5

• 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: 2,3-dimethylbenzoxazolium p-toluenesulphonate
• 英文别名: 2,3-dimethylbenzoxazole p-toluene sulfonate；2,3-dimethyl-1,3-benzoxazolium p-toluenesulfonate；2,3-dimethylbenzo[d]oxazol-3-ium 4-methylbenzenesulfonate；2,3-Dimethyl-benzoxazolium-p-toluolsulfonat；2,3-dimethyl-1,3-benzoxazol-3-ium 4-methyl-1-benzenesulfonate；2,3-dimethyl-benzooxazolium; toluene-4-sulfonate；2,3-dimethyl-benzoxazol-3-ium p-toluensulfonate；2,3-Dimethylbenzoxazolium tosylate；2,3-dimethyl-1,3-benzoxazol-3-ium;4-methylbenzenesulfonate
• CAS: 39759-82-5
• 化学式: C₇H₇O₃S*C₉H₁₀NO
• 分子量: 319.381
• InChiKey: GBBJPBIYHSMRHL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,3-Dimethyl-2-methylmercapto-3H-indol 、 2,3-dimethylbenzoxazolium p-toluenesulphonate 生成 2-(3,3-dimethyl-3H-indol-2-ylmethylene)-3-methyl-2,3-dihydro-benzooxazole
  参考文献：
  名称：

  308.烷氧基在氮环化合物中的反应性。第二部分 3,3-二甲基-2-甲硫基-3 H-吲哚的花青碱

  摘要：

  DOI：

  10.1039/jr9600001529
• 作为产物：
  描述：

  2-甲基苯并唑 、 对甲苯磺酸甲酯 反应 3.0h， 以75%的产率得到2,3-dimethylbenzoxazolium p-toluenesulphonate
  参考文献：
  名称：

  苯并二吡咯啉类双花菁染料：合成，分子结构和光谱表征

  摘要：

  一种新的长波吸收和发射双三甲胺染料的合成新方法是将苯并二吡咯啉二醛与季铵化的杂环CH-酸性化合物缩合，以制备一系列双花菁。该新方法比常规对等方法更方便，该常规对等方法是将季铵化的苯并二吡咯啉与费舍尔醛缩合，以合成包含各种杂环端基的对称取代的染料。对染料在溶液中的光谱和发光特性的研究表明，与母体“单体”花青相比，双花青素的最大吸收（596–717 nm）和最大发射（629–773 nm）红移了约100 nm。仅包含一种发色的聚次甲基系统。-1  cm -1）和量子产率（≤28％）。两个末端苯并恶唑部分均被吲哚啉，苯并噻唑，2-和4-喹啉取代，使吸收和发射最大值出现红移，但降低了量子产率。

  DOI：

  10.1016/j.dyepig.2009.09.007

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。
• Blue fluorescent dye-protein complexes based on fluorogenic cyanine dyes and single chain antibody fragments
  作者：Kimberly J. Zanotti、Gloria L. Silva、Yehuda Creeger、Kelly L. Robertson、Alan S. Waggoner、Peter B. Berget、Bruce A. Armitage

  DOI：10.1039/c0ob00444h

  日期：——

  Fluoromodules are complexes formed upon the noncovalent binding of a fluorogenic dye to its cognate biomolecular partner, which significantly enhances the fluorescence quantum yield of the dye. Previously, several single-chain, variable fragment (scFv) antibodies were selected from a yeast cell surface-displayed library that activated fluorescence from a family of unsymmetrical cyanine dyes covering much of the visible and near-IR spectrum. The current work expands our repertoire of genetically encodable scFv-dye pairs by selecting and characterizing a group of scFvs that activate fluorogenic violet-absorbing, blue-fluorescing cyanine dyes, based on oxazole and thiazole heterocycles. The dye binds to both yeast cell surface-displayed and soluble scFvs with low nanomolar Kd values. These dye-protein fluoromodules exhibit high quantum yields, approaching unity for the brightest system. The promiscuity of these scFvs with other fluorogenic cyanine dyes was also examined. Fluorescence microscopy demonstrates that the yeast cell surface-displayed scFvs can be used for multicolor imaging. The prevalence of 405 nm lasers on confocal imaging and flow cytometry systems make these new reagents potentially valuable for cell biological studies.

  氟模块是一类由荧光素与其相应生物分子伙伴之间非共价结合形成的复合物，显著增强了染料的荧光量子产率。先前，从酵母细胞表面展示文库中筛选出几种单链可变片段（scFv）抗体，它们能激活一系列覆盖大部分可见光和近红外光谱的不对称菁染料的荧光。当前工作通过筛选和表征一组激活吸收紫外光、发射蓝光的以噁唑和噻唑杂环为基础的菁染料的scFv，拓展了我们可遗传编码的scFv-染料配对组合。该染料与酵母细胞表面展示的以及可溶性scFv结合，其解离常数Kd值在低纳摩尔级别。这些染料-蛋白质氟模块显示出高量子产率，最亮系统的量子产率接近于一。此外，还考察了这些scFv与其他荧光菁染料的结合能力。荧光显微镜显示，酵母细胞表面展示的scFv可用于多色成像。由于405纳米激光在共聚焦成像和流式细胞仪系统中的普及，这些新型试剂可能对细胞生物学研究具有潜在价值。
• Development of Novel Rhodacyanine-Based Heat Shock Protein 70 Inhibitors
  作者：Chih-Shiang Chang、Vathan Kumar、Der-Yen Lee、Yeh Chen、Yu-Chieh Wu、Jing-Yan Gao、Po-Chen Chu

  DOI：10.2174/0929867328666210203204254

  日期：2021.9.8

  A growing body of evidence suggests that Hsp70, which is overexpressed in human breast tumors, plays a role in tumorigenesis and tumor progression in breast cancer as well as in its aggressive phenotypes. Hsp70 constitutes a potential therapeutic target in the treatment of this disease.

  We developed a new series of rhodacyanine-based Hsp70 inhibitors, represented by compounds 1 and 6, in which the cationic pyridin-1-ium or thiazol-3-ium ring of existing Hsp70 inhibitors (e.g., JG-40 and JG-98) was replaced by a corresponding benzo- fused N-heterocycle.

  Several lines of evidence suggest that these benzo-fused derivatives may exert their antitumor activities, in part, by targeting Hsp70. These putative inhibitors displayed differential antiproliferative efficacy against breast cancer cells (IC₅₀ as low as 0.25 μM) versus nontumorigenic MCF-10A breast epithelial cells (IC₅₀ ≥ 5 μM). This was correlated with the corresponding Hsp70 expression levels. Using a protein refolding assay, we confirmed that these agents effectively inhibited the chaperone activity of Hsp70. Moreover, these inhibitors effectively suppressed the expression of well-known oncogenic client proteins of Hsp70’s, including FoxM1, HuR, and Akt, which paralleled their antiproliferative efficacy. Supporting the established role of Hsp70 in regulating protein refolding, these derivatives induced autophagy, as manifested by the conversion of LC3B-I to LC3B-II. Notably, these putative Hsp70 inhibitors did not cause a compensatory elevation in Hsp90 expression, contrasting with the previously reported effects of Hsp90 inhibitors on Hsp70 upregulation.

  Together with the finding that compounds 1 and 6 showed improved microsomal stability, these results suggest the translational potential of these putative Hsp70 inhibitors to foster new strategies for cancer therapy. However, whether these benzo-fused rhodacyanines act on kinases or other targets remains unclear. It is currently under investigation.

  背景：越来越多的证据表明，在人类乳腺肿瘤中过度表达的Hsp70在乳腺癌的肿瘤发生和进展以及其侵袭性表型中发挥作用。Hsp70构成了治疗该疾病的潜在治疗靶点。 方法：我们开发了一系列基于罗达氰基的Hsp70抑制剂，代表物为化合物1和6，其中现有Hsp70抑制剂（例如JG-40和JG-98）的阳离子吡啶-1-ium或噻唑-3-ium环被相应的苯并N-杂环取代。 结果：多条证据表明，这些苯并融合衍生物可能部分通过靶向Hsp70发挥其抗肿瘤活性。这些假定的抑制剂对乳腺癌细胞显示出不同的抗增殖效力（IC50低至0.25μM），而对非肿瘤性MCF-10A乳腺上皮细胞的IC50≥5μM。这与相应的Hsp70表达水平相关。通过蛋白质重折叠实验，我们确认这些药物有效地抑制了Hsp70的分子伴侣活性。此外，这些抑制剂有效地抑制了Hsp70的已知致癌客体蛋白，包括FoxM1、HuR和Akt的表达，这与它们的抗增殖效力相一致。支持Hsp70在调节蛋白质重折叠中的已知作用，这些衍生物诱导了自噬，表现为LC3B-I向LC3B-II的转化。值得注意的是，这些假定的Hsp70抑制剂不会引起Hsp90表达的补偿性升高，与先前报道的Hsp90抑制剂对Hsp70上调的效应形成对比。 结论：与化合物1和6显示出改善的微粒体稳定性的发现一起，这些结果表明这些假定的Hsp70抑制剂在促进癌症治疗新策略方面具有转化潜力。然而，这些苯并融合罗达氰是否作用于激酶或其他靶点仍不清楚，目前正在进行研究。
• LUMINESCENT COMPOUNDS
  申请人：Patsenker D. Leonid

  公开号：US20070281363A1

  公开（公告）日：2007-12-06

  Reporter compounds based on cyanine dyes, among others, including reactive intermediates used to synthesize the reporter compounds, and methods of synthesizing and using the reporter compounds, among others, where the reporter compounds relate generally to the following structure:

  基于青菁染料的报告化合物，其中包括用于合成报告化合物的反应中间体，以及合成和使用报告化合物的方法，其中报告化合物通常与以下结构相关：
• Novel heterocyclic dyes as DNA markers. Part I. Synthesis and characterization
  作者：Wenceslao Moreda、Alexander R Forrester

  DOI：10.1016/s0040-4020(97)00528-0

  日期：1997.9

  A range of new cyanine dyes has been prepared and characterised. These dyes are more conveniently synthesised by the reaction of two heterocyclic quaternary salts. The dyes contain a purine heterocycle coupled to an aro-(thia-, selena-, oxa-, imida)zole and are in the form of iodide or p-toluenesulphonate salts. Characterisation were done by FABMS and NMR spectroscopy. These dyes can be used as fluorescent

  已经制备并表征了一系列新的花青染料。这些染料通过两种杂环季盐的反应更方便地合成。染料含有与芳族（硫代，硒代，氧杂，亚胺基）唑偶联的嘌呤杂环，并呈碘化物或对甲苯磺酸盐的形式。通过FABMS和NMR光谱进行表征。这些染料可用作诊断疟疾寄生虫的DNA标记的荧光染料。