1,2,6-trimethylquinolin-1-ium iodide | 31385-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,6-trimethylquinolin-1-ium iodide
• 英文别名: 1,2,6-trimethylquinolinium iodide；1,2,6-trimethylquinolium iodide；1,6-dimethylquinaldinium iodide；1,2,6-trimethyl-quinolinium; iodide；1,2,6-Trimethyl-chinolinium; Jodid；1-ethyl-2,6-dimethylquinolinium iodide；1,6-Trimethylquinolinium iodide；1,2,6-trimethylquinolin-1-ium;iodide
• CAS: 31385-19-0
• 化学式: C₁₂H₁₄N*I
• 分子量: 299.154
• InChiKey: MMXONYYYANDJOE-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2,6-trimethylquinolin-1-ium iodide 在 盐酸 、 tin 作用下， 生成 1,2,6-trimethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Synthesis in the 1,2,3,4-Tetrahydroquinoline Series

  摘要：

  DOI：

  10.1021/ja01265a078
• 作为产物：
  描述：

  2，6-二甲基喹啉 、 碘甲烷 以 异丙醇 为溶剂， 反应 12.0h， 以36%的产率得到1,2,6-trimethylquinolin-1-ium iodide
  参考文献：
  名称：

  烟酰胺N-甲基转移酶小分子抑制剂的结构-活性关系

  摘要：

  烟酰胺N-甲基转移酶（NNMT）是一种基本的胞质生物转化酶，可催化内源性和外源性异源生物的N-甲基化。我们已经确定了具有> 1000倍活性范围的NNMT小分子抑制剂，并为NNMT抑制剂开发了全面的结构-活性关系（SAR）。筛选N-甲基化的喹啉鎓，异喹啉鎓，吡啶鎓和苯并咪唑鎓/苯并噻唑鎓类似物导致鉴定出喹啉鎓是极有希望的具有极低摩尔浓度的支架（IC 50〜1μM）NNMT抑制。基于抑制剂的计算机对接至NNMT底物（烟酰胺）的结合位点在配体-酶相互作用对接得分与实验计算的IC 50值之间产生了稳固的相关性。预测的喹啉类似物的结合方向揭示了与NNMT底物结合位点残基的选择性结合以及驱动蛋白质-配体分子间相互作用和NNMT抑制的基本化学特征。这一新系列的小分子NNMT抑制剂的开发指导了类药物前体抑制剂的未来设计，以治疗以NNMT活性异常为特征的几种代谢和慢性疾病。

  DOI：

  10.1021/acs.jmedchem.7b00389

文献信息

• Antileukemic Activity of 2-Bis(2-methylthio)vinyl-1-methylquinolinium Iodides
  作者：William O. Foye、Joel M. Kauffman

  DOI：10.1002/jps.2600690434

  日期：1980.4

  -dithioacetic acid zwitterions with excess methyl iodide in dimethylformamide gave the corresponding bis(2-methylthio)vinyl derivatives. These compounds were more soluble in both aqueous and organic media than the dithioacetic acid zwitterions but showed comparable antileukemic activity in mice. Reaction with morpholine converted a bis(2-methylthio)vinyl derivative almost quantitatively to the 2-m

  1-甲基喹啉-2-二硫代乙酸两性离子与过量的甲基碘在二甲基甲酰胺中的反应得到相应的双（2-甲基硫代）乙烯基衍生物。这些化合物比二硫代乙酸两性离子更易溶于水和有机介质，但在小鼠中显示出可比的抗白血病活性。与吗啉的反应几乎定量地将双（2-甲硫基）乙烯基衍生物转化为2-单（甲硫基）-2-吗啉代衍生物。对6-甲基衍生物的白血病细胞培养研究表明对细胞周期过程没有影响。
• Pyrvinium Pamoate and Structural Analogs Are Early Macrofilaricide Leads
  作者：Emma L. Gunderson、Clifford Bryant、Christina A. Bulman、Chelsea Fischer、Mona Luo、Ian Vogel、Kee-Chong Lim、Shabnam Jawahar、Nancy Tricoche、Denis Voronin、Christopher Corbo、Rene B. Ayiseh、Faustin P. T. Manfo、Glory E. Mbah、Fidelis Cho-Ngwa、Brenda Beerntsen、Adam R. Renslo、Sara Lustigman、Judy A. Sakanari

  DOI：10.3390/ph15020189

  日期：——

  Onchocerciasis and lymphatic filariasis are neglected tropical diseases caused by infection with filarial worms. Annual or biannual mass drug administration with microfilaricidal drugs that kill the microfilarial stages of the parasites has helped reduce infection rates and thus prevent transmission of both infections. However, success depends on high population coverage that is maintained for the duration of the adult worm’s lifespan. Given that these filarial worms can live up to 14 years in their human hosts, a macrofilaricidal drug would vastly accelerate elimination efforts. Here, we have evaluated the repurposed drug pyrvinium pamoate as well as newly synthesized analogs of pyrvinium for their efficacy against filarial worms in vitro and in vivo. We found that pyrvinium pamoate, tetrahydropyrvinium and one of the analogs were highly potent in inhibiting worms in in vitro whole-worm screening assays, and that all three compounds reduced female worm fecundity and inhibited embryogenesis in the Brugia pahangi-gerbil in vivo model of infection.

  Onchocerciasis和淋巴丝虫病是由丝虫感染引起的热带忽视病。每年或每两年进行大规模服药治疗，使用杀灭寄生虫微丝阶段的药物有助于降低感染率，从而防止这两种感染的传播。然而，成功取决于高人口覆盖率，在成虫寿命期间保持这种覆盖率。考虑到这些丝虫可以在宿主人体中存活长达14年，一种杀灭成虫的药物将大大加速消除工作。在这里，我们评估了改良药物吡硫酸吡唑以及新合成的吡硫酸吡唑类似物对体内外丝虫的有效性。我们发现，吡硫酸吡唑、四氢吡硫酸吡唑和其中一个类似物在体外全虫筛选实验中抑制虫子的效果非常明显，并且这三种化合物均降低了雌性虫的繁殖能力，并在Brugia pahangi-鼠类感染模型中抑制了胚胎发育。
• Moeller, Justus Liebigs Annalen der Chemie, 1887, vol. 242, p. 313
  作者：Moeller

  DOI：——

  日期：——
• Structure-inherent near-infrared fluorescent probe mediates apoptosis imaging and targeted drug delivery in vivo
  作者：Xianghan Zhang、Na Zhao、Bo Wang、Zuhong Tian、Yunpeng Dai、Pengbo Ning、Dan Chen

  DOI：10.1016/j.dyepig.2016.11.022

  日期：2017.3

  Imaging of tumor apoptosis can provide invaluable information in regards to drug treatment effectiveness, drug development and tumor therapeutic response. Thus, the development of apoptotic specific and sensitive targeted fluorescence probes is critically needed. In this work, we developed a novel and simple one-step synthetic method for producing monocarboxylate near-infrared cyanine dyes. The hydrophobic cationic dyes possess advantageous optical properties and good membrane permeability. One hydrophilic zwitterionic probe is able to both increase specificity and image apoptotic cells owing to its inherent chemical structure. Furthermore, we conjugated the probe with the antitumor drug gemcitabine for effective apoptosis imaging and therapeutic targeting of gastric tumors in vitro and in vivo. The novel dye-drug conjugate imaged apoptosis successfully in vitro and in vivo and restricted the growth of SGC7901 subcutaneous xenograft models. This strategy may offer the advantages of NIR apoptosis imaging probes for non-invasive tumor imaging and should provide the application for targeted drug delivery and the evaluation of therapeutic efficacy. (C) 2016 Elsevier Ltd. All rights reserved.
• Rusinov; Plekhanov; Rusinov, Russian Journal of Organic Chemistry, 1998, vol. 34, # 2, p. 263 - 270
  作者：Rusinov、Plekhanov、Rusinov、Chupakhin、Aleksandrov

  DOI：——

  日期：——