3-(2-fluorophenylthio)quinoline | 1299398-28-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(2-fluorophenylthio)quinoline
• 英文别名: 3-(2-Fluorophenyl)sulfanylquinoline
• CAS: 1299398-28-9
• 化学式: C₁₅H₁₀FNS
• 分子量: 255.316
• InChiKey: UJTZMBBMKRQHJF-UHFFFAOYSA-N

物化性质

• 沸点：
  375.6±22.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-fluorophenylthio)quinoline 、 (5-碘戊基)苯 以 环丁砜 为溶剂， 以53%的产率得到3-(2-fluorophenylsulfanyl)-1-(5-phenylpentyl)quinolin-1-ium iodide
  参考文献：
  名称：

  Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens

  摘要：

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.02.034
• 作为产物：
  描述：

  3-溴喹啉 在 copper(l) iodide 、 potassium carbonate 、 乙二醇 、 sodium iodide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 78.0h， 生成 3-(2-fluorophenylthio)quinoline
  参考文献：
  名称：

  Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens

  摘要：

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.02.034

文献信息

• Nickel-Catalyzed Site-Selective C3–H Functionalization of Quinolines with Electrophilic Reagents at Room Temperature
  作者：Xinghao Sheng、Mingpan Yan、Bo Zhang、Wai-Yeung Wong、Nobuaki Kambe、Renhua Qiu

  DOI：10.1021/acscatal.3c01553

  日期：2023.7.21

  Herein, we disclose a mild and versatile nickel-catalyzed method for exclusive C3-selective thioetherification, alkylation, arylation, acylation, and phosphorylation of quinolines with a variety of electrophiles. Unactivated quinolines can be functionalized without directing groups at room temperature. Control experiments indicated that quinolines underwent 1,4-addition with nickel hydride species

  在此，我们公开了一种温和且通用的镍催化方法，用于喹啉与各种亲电子试剂的排他性C3选择性硫醚化、烷基化、芳基化、酰化和磷酸化。未活化的喹啉可以在室温下无需定向基团即可官能化。对照实验表明，喹啉与烷基镍中间体β-H消除产生的氢化镍物质进行1,4-加成反应生成1,4-二氢喹啉，进一步通过随后对外部亲电试剂的亲核攻击和氧化芳构化生成C3-H功能化产物。
• Structural Simplification of Cryptolepine to Obtain Novel Antifungal Quinoline Derivatives against Phytopathogenic Fungi
  作者：Hai-Xin Li、Xiong-Fei Luo、Peng Deng、Shao-Yong Zhang、Han Zhou、Yan Yan Ding、Yi-Rong Wang、Ying-Qian Liu、Zhi-Jun Zhang

  DOI：10.1021/acs.jafc.2c07575

  日期：2023.2.8
• Optimization of 3-(phenylthio)quinolinium compounds against opportunistic fungal pathogens
  作者：Comfort A. Boateng、Xue Y. Zhu、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.ejmech.2011.02.034

  日期：2011.5

  Ring-opened benzothieno[3,2-b]quinolinium salts (3) were designed and synthesized with substitution on the thiophene moiety. In vitro screenings were carried out against fungal pathogens including Cryptococcus neoformans, Candida albicans, Candida glabrata, Candida krusei and Aspergillus fumigatus. In all, by replacing the N-methyl group (2) with N-omega-phenylpentyl or omega-cyclohexylpentyl group to form substituted 3-(phenylthio)quinolinium compounds produced remarkable potencies, as high as 300-fold (cf. cryptolepine (1) = 250 mu g/mL vs lip = 0.8 mu g/mL for C. albicans) over the starting tetracyclic parent. In addition, all the N-omega-cyclohexylpentyl analogs produced superior activity against all the microorganisms tested than the N-omega-phenylpentyl substituted compounds. The potential of these compounds to induce toxicity in Vero cells was also investigated and the majority of them showed lower or no cytotoxicity at 10 mu g/mL than amphotericin B. the gold standard in antifungal drug development. For instance, the trifluoromethyl substituted analogs (11n-p) have selectivity indices over 2-fold better than those of amphotericin B in C. neoformans. Overall, this ring-opened scafford of benzothienoquinolines, with substitution on the thiophenyl moiety, serves as a new lead for further development. Published by Elsevier Masson SAS.